1. Trang chủ
  2. » Tất cả

British journal of pharmacology 2015 volume 172 part 3

237 368 0
Tài liệu đã được kiểm tra trùng lặp

Đang tải... (xem toàn văn)

Tài liệu hạn chế xem trước, để xem đầy đủ mời bạn chọn Tải xuống

THÔNG TIN TÀI LIỆU

Thông tin cơ bản

Định dạng
Số trang 237
Dung lượng 28,23 MB

Các công cụ chuyển đổi và chỉnh sửa cho tài liệu này

Nội dung

Abbreviations ANP, atrial natriuretic peptide; CAD, coronary artery disease; CVD, cardiovascular disease; DPP-4, dipeptidyl peptidase-4; eNOS, endothelial NOS; GLP-1, glucagon-like pepti

Trang 1

David J Grieve, Centre forExperimental Medicine, Queen’sUniversity Belfast, Institute ofClinical Science Block A,Grosvenor Road, BelfastBT12 6BA, UK E-mail:

Glucagon-like peptide-1 (GLP-1) is an incretin hormone whose glucose-dependent insulinotropic actions have been harnessed

as a novel therapy for glycaemic control in type 2 diabetes Although it has been known for some time that the GLP-1receptor is expressed in the CVS where it mediates important physiological actions, it is only recently that specific

cardiovascular effects of GLP-1 in the setting of diabetes have been described GLP-1 confers indirect benefits in cardiovasculardisease (CVD) under both normal and hyperglycaemic conditions via reducing established risk factors, such as hypertension,dyslipidaemia and obesity, which are markedly increased in diabetes Emerging evidence indicates that GLP-1 also exertsdirect effects on specific aspects of diabetic CVD, such as endothelial dysfunction, inflammation, angiogenesis and adversecardiac remodelling However, the majority of studies have employed experimental models of diabetic CVD and information

on the effects of GLP-1 in the clinical setting is limited, although several large-scale trials are ongoing It is clearly important

to gain a detailed knowledge of the cardiovascular actions of GLP-1 in diabetes given the large number of patients currentlyreceiving GLP-1-based therapies This review will therefore discuss current understanding of the effects of GLP-1 on bothcardiovascular risk factors in diabetes and direct actions on the heart and vasculature in this setting and the evidence

implicating specific targeting of GLP-1 as a novel therapy for CVD in diabetes

Abbreviations

ANP, atrial natriuretic peptide; CAD, coronary artery disease; CVD, cardiovascular disease; DPP-4, dipeptidyl

peptidase-4; eNOS, endothelial NOS; GLP-1, glucagon-like peptide-1; hs-CRP, high sensitivity C-reactive protein;

ICAM-1, intercellular adhesion molecule-1; MI, myocardial infarction; PAI-1, plasminogen activator inhibitor-1; STZ,streptozotocin; T1DM, type 1 diabetes mellitus; T2DM, type 2 diabetes mellitus; TLR, toll-like receptor; UKPDS, UnitedKingdom Prospective Diabetes Study; VCAM-1, vascular cell adhesion molecule-1

Trang 2

The prevalence of type 2 diabetes mellitus (T2DM) is

increas-ing alarmincreas-ingly with the 2013 figure of 382 million estimated

to rise to 592 million by 2035 (International Diabetes

Federation, 2014) A change in lifestyle coupled with an

increase in obesity has led to a global epidemic, with diabetics

typically carrying a fivefold greater mortality risk as a result of

cardiovascular disease (CVD) compared with non-diabetics

(Stamler et al., 1993), and coronary artery disease (CAD)

being the leading underlying cause (Bertoni et al., 2004) It is

well established that hyperglycaemia plays a central role in

development and progression of CVD associated with

diabe-tes (Nathan, 1996) Indeed, two long-term clinical trials, the

Diabetes Control and Complications Trial/Epidemiology of

Diabetes Interventions and Complications study and the

United Kingdom Prospective Diabetes Study (UKPDS), have

demonstrated that intensive glucose-lowering strategies are

effective in markedly reducing the incidence of microvascular

(e.g retinopathy, nephropathy) and macrovascular (e.g

CAD, stroke) complications in both type 1 diabetes mellitus

(T1DM) and T2DM (Holman et al., 2008), although several

similar large-scale trials have reported limited benefits

(Action to Control Cardiovascular Risk in Diabetes Study

Group, 2008; Duckworth et al., 2009; Ginsberg, 2011)

None-theless, there remains a significant incidence of CVD even in

optimally treated diabetic patients, so it is clear that more

effective strategies are required In this regard, the incretin

peptide hormone, glucagon-like peptide-1 (GLP-1), has

received considerable recent attention

The incretin effect is responsible for augmenting insulin

secretion following nutrient ingestion and GLP-1 together

with its sister hormone, gastrointestinal peptide, account for

up to 60% of post-prandial insulin secretion, leading to rapid

blood glucose reduction (Nauck et al., 1986; Drucker et al.,

1987) Furthermore, they possess an inherent ability to

reduce glucagon secretion (Kreymann et al., 1987), delay gastric emptying (Näslund et al., 1998a) and promote satiety (Flint et al., 1998) The metabolic actions of GLP-1 are medi-

ated by GLP-1 receptor activation and stimulation of cAMPand several downstream kinases, including ERK1/2, PI3K andPKA Under physiological conditions, GLP-1 has a short half-life (∼2 min) as it is rapidly degraded by its endogenous

inhibitor, dipeptidyl peptidase-4 (DPP-4) (Deacon et al.,

1995), resulting in cleavage of two amino acids from nativeGLP-1(7-36) to produce GLP-1(9-36), which acts as a weakGLP-1 receptor antagonist lacking insulinotropic activity

(Green et al., 2004) However, emerging evidence suggests

that ‘metabolically inactive’ GLP-1(9-36) may itself be an

important signalling molecule (Ban et al., 2010; Gardiner

et al., 2010) More detailed information on GLP-1 biology and

signalling is provided by recent review articles (Grieve et al., 2009; Donnelly, 2012; Pabreja et al., 2013).

The unique ability of GLP-1 to promote insulin secretion

in a glucose-dependent manner has been harnessed for ment of T2DM, with GLP-1 receptor agonists resistant toDPP-4 (exenatide, Byetta®; liraglutide, Victoza®), and DPP-4inhibitors (e.g sitagliptin, vildagliptin) now widely used foreffective glycaemic control Interestingly, it is well recognizedthat GLP-1 exerts wide-ranging extra-pancreatic actionsoccurring independently of its established metabolic effects.Indeed, GLP-1 signalling is reported to play several important

treat-roles in the CVS in both health and disease (Grieve et al.,

2009), although it appears that the GLP-1 receptor may not

These Tables list key protein targets and ligands in this article which are hyperlinked to corresponding entries in http://

www.guidetopharmacology.org, the common portal for data from the IUPHAR/BPS Guide to PHARMACOLOGY (Pawson et al., 2014) and are

permanently archived in the Concise Guide to PHARMACOLOGY 2013/14 (a,b,c,d,e Alexander et al., 2013a,b,c,d,e).

Trang 3

be as widely expressed as previously thought For example,

recent work suggests that cardiac GLP-1 receptor expression

may be localized to atrial tissue, sinoatrial node and

vascula-ture, with some species variation (Kim et al., 2013; Pyke et al.,

2014; Richards et al., 2014), and that earlier reports of more

ubiquitous expression may be questionable because of poor

antibody selectivity and sensitivity (Panjwani et al., 2012).

Nonetheless, it is clear that GLP-1 exerts important

cardio-vascular actions, although it is only recently that its effects in

the setting of diabetes, a condition synonymous with micro/

macrovascular complications, have been explored This is

clearly important because of the large number of patients

receiving GLP-1-based therapies, in which its cardiovascular

actions are largely unknown This review will therefore

discuss the current understanding of the effects of GLP-1 on

both cardiovascular risk factors in diabetes and direct actions

on the heart/vasculature in this setting and the evidence

implicating specific targeting of GLP-1 as a novel therapy for

CVD in diabetes, with a primary focus on the role of GLP-1

receptor agonists More detailed discussion of the pleiotropic

actions of DPP-4 inhibitors in this setting is provided by

recent review articles specifically focused on this important

aspect of cardiovascular GLP-1 signalling (Scheen, 2013;

Aroor et al., 2014).

Influence of GLP-1 on cardiovascular

risk factors in diabetes

BP and hypertension

Increased BP is an established risk factor for CVD in both

normoglycaemia and T2DM (Turner et al., 1998; Vasan et al.,

2001) Notably, therapeutic reductions in BP and circulating

glucose have an additive effect in decreasing cardiovascular

complications in T2DM patients, as highlighted by the

UKPDS (Stratton et al., 2006) Indeed, in an experimental

setting, chronic GLP-1 infusion inhibits development of

hypertension in Dahl salt-sensitive rats, as well as reducing

cardiac fibrosis and hypertrophy, effects which appear to

occur via a natriuretic/diuretic mechanism independently of

blood glucose (Yu et al., 2003), suggesting that GLP-1 may

confer additional benefits which could be harnessed for the

treatment of hypertension associated with T2DM Consistent

with an indirect BP-lowering effect, it was recently reported

that liraglutide-stimulated reduction of angiotensin

II-induced hypertension in mice was blocked by the natriuretic

peptide receptor antagonist, anantin, in a GLP-1

receptor-dependent manner, but unaltered by the NOS inhibitor, NG

-monomethyl-L-arginine, and that liraglutide induced rapid

increases in atrial natriuretic peptide (ANP) secretion both in

vivo and in isolated perfused hearts, suggesting that observed

BP reduction occurred at least partly via direct activation of

cardiac ANP (Kim et al., 2013) Importantly, in the context of

diabetes, the GLP-1 mimetic, exendin-4, inhibited

develop-ment of both spontaneous and high salt-induced

hyperten-sion in obese db/db mice via beneficial actions on renal

sodium handling (Hirata et al., 2009) Furthermore, it was

recently reported that treatment of insulin-resistant Zucker

rats with the DPP-4 inhibitor, linagliptin, for 8 weeks reduced

BP and improved diastolic function (Aroor et al., 2013).

Interestingly, although chronic administration of GLP-1may prevent development of hypertension, it is widelyreported that acute GLP-1 exposure is associated withincreased BP and heart rate, which predisposes to CVD Forexample, acute infusion of GLP-1(7-36) increased systolic/diastolic BP and heart rate in both normal and insulin-deficient streptozotocin (STZ)-induced T1DM rats (Barragán

et al., 1994), with the same group reporting that

exendin-4-induced increases in BP and heart rate were reversed by the

GLP-1 receptor antagonist, exendin(9-39) (Barragán et al.,

1996), suggesting that these effects occurred via an independent mechanism but involving GLP-1 receptor acti-vation Although similar increases in BP and heart rate aftershort-term GLP-1 administration have been reported in

insulin-various experimental models (Grieve et al., 2009), the data

from clinical studies are less clear For example, GLP-1 sion in a small number of T2DM patients with or withoutCAD for 105 min and 48 h, respectively, had no effect on

infu-heart rate or systolic/diastolic BP (Toft-Nielsen et al., 1999; Nystrưm et al., 2004), whereas 48 h GLP-1 infusion in patients with ischaemic heart failure (Halbirk et al., 2010) and

treatment of T2DM patients with an exendin-transferrinfusion protein or exenatide for 7 or 10 days, respectively

(Kothare et al., 2008; Gustavson et al., 2011), resulted in

elevated heart rate and diastolic BP However, the data fromlonger-term GLP-1 clinical trials are more consistent, with themajority reporting decreased BP and minimal effects on heartrate For example, the Liraglutide Effect and Action in Diabe-tes (LEAD)-4 study, investigating 26 week liraglutide treat-ment in combination with metformin in T2DM patients,reported a modest reduction in systolic BP of 6 mmHg com-

pared with placebo (1.1 mmHg) (Zinman et al., 2009)

Simi-larly, the LEAD-2 study, assessing liraglutide combinationtherapy, reported a 2–3 mmHg decrease in systolic BP versus

a small increase (0.4 mmHg) in the glimepiride control group

(Nauck et al., 2009) Furthermore, a 30 week trial comparing

once-weekly versus twice-daily exenatide injection in nạve T2DM patients observed a significant decrease in

drug-systolic/diastolic BP compared with baseline (Drucker et al.,

2008), while another 20 week trial in obese patients reportedreduced systolic/diastolic BP in response to liraglutide, which

persisted for the 2 year follow-up period (Astrup et al., 2012).

Interestingly, meta-analysis of six clinical trials comprising

2171 T2DM patients found that exenatide treatment for 6months produced maximal systolic BP reduction in individu-als with abnormally high baseline levels, whereas no effects

were observed in normotensive subjects (Okerson et al.,

2010) It should be noted that BP reduction is positively

correlated with weight loss (Neter et al., 2003), so it is possible

that the observed changes after chronic GLP-1 treatment mayoccur secondary to its metabolic effects However, althoughbeneficial effects of GLP-1 on body weight are associated withimproved hypertension, it is clear that this cannot solelyaccount for its vascular effects as several studies have reported

a BP reduction prior to weight loss For example, a combinedmeta-analysis of three 26 week liraglutide trials reporteddecreased BP after only 2 weeks, while maximal weight loss

did not occur until 8 weeks (Gallwitz et al., 2010) Indeed,

heart rate, which is not linked to body weight, was increased

by chronic administration of both liraglutide and exenatide

in T2DM patients in parallel with reduced systolic BP (Garber

Trang 4

et al., 2009; Gill et al., 2010) Interestingly, it was recently

reported that GLP-1 secretory function increases with age and

is negatively correlated with systolic BP, suggesting that this

may represent an adaptive response (Yoshihara et al., 2013).

Dyslipidaemia

The pathophysiology of diabetes is commonly considered

largely in terms of associated hyperglycaemia However, it is

increasingly apparent that dyslipidaemia is equally important

and represents a significant risk factor for CVD in diabetic

patients (Reiner et al., 2011) It is likely that impaired insulin

sensitivity contributes to dyslipidaemia in T2DM, which is

associated with reduced GLP-1 secretion Indeed, in addition

to their established glycaemic actions, GLP-1 receptor

activa-tion and DPP-4 inhibiactiva-tion are reported to improve lipid

pro-files in both experimental and clinical diabetes For example,

short-term infusion of GLP-1 in normoglycaemic Syrian

golden hamsters decreased lipid absorption and triglyceride

levels, an effect potentiated by oral glucose (Hein et al., 2013),

suggesting that its incretin action may inhibit intestinal

pro-duction of chylomicrons, which are strongly linked to

ath-erosclerosis (Nakano et al., 2008) Similarly, circulating

triglycerides and fat pad mass in rats with diet-induced

obesity were reduced after 4 week treatment with liraglutide

(Madsen et al., 2010), while 40 day administration of

exendin-4 ameliorated systemic and cardiac insulin

resist-ance and dyslipidaemia in both genetic KKAy and

Furthermore, chronic GLP-1 receptor activation with both

the GLP-1 analogue, CNTO3649, and exendin-4 in

apolipo-protein E3-Leiden transgenic mice, which develop severe

hypercholesterolaemia after high-fat feeding, resulted in

reduced very-low-density lipoprotein (VLDL)-triglyceride

and apolipoprotein B synthesis in parallel with decreased

hepatic triglyceride, cholesterol and phospholipids and

lipo-genesis gene expression (Parlevliet et al., 2012) The

long-acting DPP-4 inhibitor, teneligliptin, is also reported to

decrease circulating triglyceride and free fatty acid levels in

insulin-resistant Zucker fatty rats after 2 week treatment

(Fukuda-Tsuru et al., 2012).

Importantly, the majority of clinical studies have also

demonstrated beneficial outcomes of GLP-1 administration

on lipid metabolism in T2DM, such as reduced circulating

triglycerides and low-density lipoprotein (LDL) cholesterol

(Flock et al., 2007; Drucker et al., 2008; Tremblay et al., 2011),

although one study in which patients were treated with

exenatide for 24 weeks reported a similar plasma lipid profile

versus controls (Moretto et al., 2008) For example, decreased

circulating levels of atherogenic triglyceride-rich lipoproteins

were observed following 4 week vildagliptin monotherapy in

drug-nạve T2DM patients, characterized by specific

reduc-tions in total plasma and chylomicron triglycerides, together

with apolipoprotein B-48 and cholesterol in the chylomicron

subfraction (Matikainen et al., 2006) Furthermore, the

LEAD-4 study found that 26 week liraglutide treatment in

combination with metformin and rosiglitazone decreased

cir-culating LDL cholesterol, triglycerides and free fatty acids in

T2DM patients compared with placebo controls, although it

is interesting to note that these changes were greater in

response to low-dose treatment (Zinman et al., 2009) Indeed,

similar results are reported for DPP-4 inhibitors, which

produce much lower circulating levels of GLP-1 For example,twice-daily sitagliptin led to a significant reduction in circu-lating triglycerides and free fatty acids in a large number ofT2DM patients compared with placebo and glipizide controlgroups, despite similar decreases in fasting plasma glucose

and HbA1c levels (Scott et al., 2007) Interestingly, a single

injection of exenatide was shown to attenuate postprandialincreases in triglycerides, apolipoprotein B-48 and CIII/remnant lipoprotein cholesterol for up to 8 h in patients withimpaired glucose tolerance and recent-onset T2DM (Schwartz

et al., 2010), suggesting that such lipid profile benefits may

not be explained solely by chronic changes in body weight,glucose levels and insulin resistance Indeed, it was recentlyreported that exendin-4 completely reverses hepatic steatosis

in mice fed a high-fat diet via a GLP-1 receptor-dependentmechanism resulting in reduced numbers/size of circulatingVLDL-triglyceride and VLDL-apolipoprotein B particles

(Parlevliet et al., 2012), suggesting that GLP-1 may exert

direct effects on dyslipidaemia in diabetes

Obesity

Although it is well known that obesity significantly increases

the risk of T2DM (Willett et al., 1999), and both are ent risk factors for CVD (Hubert et al., 1983), many estab-

independ-lished diabetes therapies, including sulfonylureas andthiazolidinediones, may increase body weight However,GLP-1 reduces body weight because of beneficial effects onglucagon secretion, gastric emptying and satiety (Kreymann

et al., 1987; Flint et al., 1998; Näslund et al., 1998a), so it

seems likely that impaired GLP-1 secretion observed in

non-diabetic obese individuals (Holst et al., 1982; Näslund et al.,

1998b) may at least partly account for their increased bodyweight Indeed, weight loss improves the postprandial GLP-1

response in severely obese patients (Verdich et al., 2001),

sug-gesting that the two are interlinked Furthermore, a 20 weektreatment with liraglutide was reported to cause significantweight loss in obese individuals and to reduce the incidence

of prediabetes (Astrup et al., 2009), confirming an apparent

role for GLP-1 in weight control which may be harnessed fortherapeutic benefit This assertion is supported by the LEADtrials which have consistently reported a reduction in bodyweight in T2DM patients following liraglutide treatment

(Moretto et al., 2008; Buse et al., 2009; Garber et al., 2009; Nauck et al., 2009; 2013; Zinman et al., 2009) For example, in

the LEAD-2 trial, 26 week combination therapy of liraglutidewith metformin in T2DM patients resulted in increased

weight loss compared with metformin alone (Nauck et al.,

2013) Importantly, weight loss associated with both tide and exenatide treatment is reported to be linked toimproved cardiovascular risk factors, such as HbA1c and BP,

liraglu-and to persist for at least 2 years (Klonoff et al., 2007; Astrup

et al., 2009; 2012), highlighting important benefits of GLP-1

which may not be related to its insulinotropic actions Thelong-term effects of GLP-1 on weight loss may be particularlyimportant as conventional weight loss is typically poorlymaintained in T2DM patients Despite GLP-1 receptor ago-nists promoting weight loss in both diabetic and non-diabeticobese subjects, DPP-4 inhibitors appear to be weight-neutral

(Amori et al., 2007), suggesting that GLP-1 receptor agonists

may exert direct gastrointestinal effects in addition to

improving insulin resistance (Rask et al., 2001), although this

Trang 5

could simply be due to differences in circulating GLP-1 levels.

However, postprandial GLP-1 levels are reported to be

increased immediately after gastric bypass surgery, despite

patients remaining obese, indicating that GLP-1 may regulate

appetite and food intake directly (Morinigo et al., 2006).

Indeed, in T2DM patients, GLP-1 promotes satiety, thereby

reducing energy consumption (Gutzwiller et al., 1999), while

in healthy individuals i.v administration of GLP-1(7-36)

slows gastric emptying in a dose-dependent manner (Nauck

et al., 1997).

GLP-1 and vascular disease

Vascular function

Impaired endothelial and vascular function are established as

key initiating factors underlying the development of

micro-vascular and macromicro-vascular complications associated with

diabetes Indeed, it has been known for some time that native

GLP-1(7-36) induces ex vivo dose-dependent vasodilatation

in a number of isolated rodent vessels, including aorta

(Golpon et al., 2001; Green et al., 2008), pulmonary artery

(Richter et al., 1993; Golpon et al., 2001), femoral artery

(Nyström et al., 2005) and mesenteric artery (Ban et al., 2008),

although several different mechanisms have been proposed

For example, some studies indicate that the vasorelaxant

actions of GLP-1 are dependent upon endothelium-derived

NO (Golpon et al., 2001; Ban et al., 2008; Gaspari et al., 2011),

whereas others have proposed endothelium-independent

mechanisms involving mediators such as KATP channels,

cAMP andβ2-adrenoceptor activation (Nyström et al., 2005;

Gardiner et al., 2008; Green et al., 2008) Interestingly,

although several studies suggest that the vascular actions of

GLP-1 are dependent upon the GLP-1 receptor (Gaspari et al.,

2011; Chai et al., 2012), it appears that they may also be

mediated, at least partly, by its truncated metabolite,

GLP-1(9-36), which induces dose-dependent relaxation in both

isolated mouse mesenteric artery (Ban et al., 2008) and rat

aorta (Green et al., 2008) It should be noted that although

the synthetic GLP-1 mimetic, exendin-4, exerts similar

actions in rat aorta (Golpon et al., 2001; Green et al., 2008),

they are of reduced magnitude compared with GLP-1(7-36)

and are absent in mouse mesenteric artery (Ban et al., 2008).

Importantly, the vasorelaxant actions of GLP-1 are also

reported in vivo For example, systemic administration of

GLP-1(7-36) by both bolus dose and short-term infusion in

rats induced hindquarters vasodilatation (Gardiner et al.,

2010) Interestingly, however, GLP-1 promoted

vasoconstric-tion in both mesenteric and renal arteries, while exendin-4

exerted similar vasoconstriction in mesenteric artery but

induced vasodilatation in both hindquarters and renal artery

(Gardiner et al., 2008), suggesting differential vascular effects.

Indeed, a similar study demonstrated that GLP-1(7-36)

infu-sion acutely increased muscle microvascular blood volume in

the absence of changes in microvascular blood flow velocity

or femoral blood flow, in association with increased plasma

NO, muscle insulin clearance/uptake, hindlimb glucose

extraction and muscle interstitial oxygen saturation (Chai

et al., 2012) It should be noted that in contrast to the ex vivo

studies, GLP-1(9-36) failed to modulate vascular function in

rats in vivo when given as either a bolus dose or via short-term

infusion, which together with the fact that DPP-4 inhibitorsprolonged the vascular actions of native GLP-1(7-36) in this

setting (Gardiner et al., 2010), suggest that the actions of this

‘inactive’ metabolite may not be significant in vivo.

Importantly, it appears that the vascular effects of GLP-1are also evident in the setting of diabetes, where they arereported to promote beneficial actions Chronic treatment ofSTZ/nicotinamide T1DM rats with either GLP-1(7-36) orexendin-4 was shown to prevent endothelial dysfunction in

parallel with reduction of blood glucose (Özyazgan et al.,

2005), effects which may be mediated via activation of

endothelial NOS (eNOS) (Goyal et al., 2010) Although

similar studies have not been performed in the setting ofovert T2DM, it was recently reported that chronic treatment

of insulin-resistant Zucker rats with the DPP-4 inhibitor, gliptin, resulted in reduced hypertension in parallel withincreased expression of total/phosphorylated eNOS (Aroor

lina-et al., 2013) Furthermore, high-fat fed apolipoprotein

E-deficient mice treated with a different DPP-4 inhibitor, fluoro-sitagliptin, demonstrated attenuation of endothelialdysfunction in parallel with eNOS activation and improved

des-glucose tolerance (Matsubara et al., 2012) Interestingly,

however, endothelial dysfunction in rat femoral arteryinduced by short-term triglyceride exposure was not affected

by exendin-4 (Nathanson et al., 2009), suggesting that the reported in vivo protective actions may occur via indirect

mechanisms In this regard, it is important to note that thevascular actions of GLP-1 in diabetes are likely to occur, atleast partly, secondary to stimulation of insulin, whichinduces vascular relaxation via Ca2+-dependent activation of

eNOS (Han et al., 1995; Kahn et al., 1998).

In addition to the data supporting important vascularactions of GLP-1 in experimental diabetes, several studieshave reported beneficial functional effects in the clinicalsetting For example, in T2DM patients with stable CAD,acute GLP-1 administration improved brachial artery flow-mediated vasodilatation, an effect not observed in healthy

individuals (Nyström et al., 2004) Comparable effects were

observed in insulin-resistant patients with obesity-relatedmetabolic syndrome, where acute treatment with GLP-1(7-36) enhanced insulin-mediated forearm blood flow responses

to both ACh and sodium nitroprusside in the absence ofchanges in forearm glucose extraction/uptake, while GLP-

1(9-36) did not affect vascular function (Tesauro et al., 2013).

Similarly, in patients with T1DM, brachial artery endothelialdysfunction induced by acute blood glucose modulation wascounteracted by simultaneous infusion of GLP-1 (Ceriello

et al., 2013) Interestingly, GLP-1-induced enhancement of

endothelium-dependent peripheral vasodilatation observed

in non-diabetic individuals is differentially modulated bysulphonylureas, with glyburide abolishing GLP-1-inducedACh-mediated responses which are unaltered by glimepiride

(Basu et al., 2007) Furthermore exenatide, which is

com-monly used for hyperglycaemic control in T2DM, alsoincreased postprandial endothelial function assessed byperipheral arterial tonometry in patients with recent-onsetdisease when given as a single dose, largely secondary to a

reduction in circulating triglycerides (Koska et al., 2010),

although chronic treatment for 3 months in obese betic patients had no additional effect when compared with

Trang 6

predia-those receiving metformin (Kelly et al., 2012) While it

appears that clinical GLP-1 administration exerts acute

vas-cular effects in T2DM, data on its chronic actions in this

setting are variable T2DM patients who received exenatide

for a period of 4 months as an adjunct to standard metformin

therapy demonstrated improved brachial artery

flow-mediated dilatation, indicated by elevated peak dilatation

and shear rate which are reflective of improved

macrovascu-lar and microvascumacrovascu-lar function respectively (Irace et al.,

2013) Notably, enhanced vasodilatation in exenatide-treated

patients in this study was significantly greater than that

observed in those receiving glimepiride as an add-on to

met-formin therapy Furthermore, liraglutide treatment for 12

weeks in T2DM patients well controlled on metformin

mono-therapy resulted in an improvement in both circulating

markers of vascular function [asymmetric dimethylarginine,

plasminogen activator inhibitor-1 (PAI-1), E-selectin] and

retinal microvascular endothelial function (Forst et al., 2012).

However, a similar study in a small number of severely obese

T2DM patients chronically treated with GLP-1 receptor

ago-nists for 6 months reported that neither exenatide or

liraglu-tide had any effect on brachial artery endothelial-dependent

flow-mediated dilation (Hopkins et al., 2013), indicating

potential for other confounding factors in this setting which

may need to be considered Furthermore, 6 week treatment

with sitagliptin or alogliptin significantly reduced

flow-mediated dilatation in male T2DM patients (Ayaori et al.,

2013), suggesting that chronically increased physiological

levels of GLP-1 may exert unfavourable vascular actions,

although it is possible that this could be a class-specific effect

of DPP-4 inhibitors warranting further investigation

Inflammation and atherosclerosis

It is well known that the incidence and progression of

endothelial dysfunction is exacerbated in T2DM, secondary

to established risk factors, such as insulin resistance,

dyslipi-daemia and hyperglycaemia Endothelial dysfunction in this

setting is characterized by an elevation in circulating

adhe-sion molecules, such as intercellular adheadhe-sion molecule-1

(ICAM-1) and vascular cell adhesion molecule-1 (VCAM-1),

and an increased propensity to develop atherosclerosis which

is typified by inflammatory cell infiltration and plaque

for-mation (Van Gaal et al., 2006) Interestingly, several recent

clinical and experimental studies appear to indicate that

GLP-1 exerts both anti-inflammatory and anti-atherogenic

actions For example, GLP-1 treatment in T2DM patients is

associated with beneficial effects on a number of established

CVD biomarkers, including high sensitivity C-reactive

protein (hs-CRP) and PAI-1, which are important in

athero-sclerosis development (Haffner, 2006) Similarly, 14 week

treatment of T2DM patients with liraglutide resulted in

sig-nificantly reduced PAI-1 levels, and a dose-dependent

decrease in plasma hs-CRP levels (Vilsbøll et al., 2007;

Courrèges et al., 2008), an effect that was also observed after

26 week treatment with exenatide (Bergenstal et al., 2010)

and was over and above that seen in patients treated with

insulin glargine (Diamant et al., 2010) Importantly, the

ben-eficial effects of exenatide on circulating hs-CRP appear to

persist at 1 year treatment in T2DM patients receiving

stand-ard metformin therapy, resulting in reduced levels of both

hs-CRP and leptin (Bunck et al., 2010) DPP-4 inhibitors seem

to exert similar effects as T2DM patients receiving sitagliptinfor 6 months also demonstrated significant reductions inplasma hs-CRP, together with VCAM-1 and associated albu-minuria, which may attenuate glucose excursion and inhibit

vascular inflammation (Horváth et al., 2009; Hattori, 2010).

Interestingly, a recent study demonstrated that cessation ofexenatide treatment resulted in the reversal of benefits on

circulating hs-CRP within 6 months (Varanasi et al., 2011) It

should be noted that although these studies support thesuggestion that GLP-1 may protect against inflammation andatherosclerosis in the clinical setting, it is not possible to drawclear conclusions because of the absence of longer-termstudies specifically assessing effects on disease development.Interestingly, a recent study has reported a positive correla-tion between circulating GLP-1 levels and CAD in both dia-betic and non-diabetic patients undergoing angiographybecause of typical or atypical chest pain, highlighting thepossibility that GLP-1 may exert detrimental effects in this

setting (Piotrowski et al., 2013).

Nonetheless, the majority of clinical data are broadly portive of the anti-inflammatory actions of GLP-1, whichpersist for up to 12 weeks in obese T2DM patients after a

sup-single exenatide injection (Chaudhuri et al., 2011) Indeed, in

this study, GLP-1 was associated with a specific reduction ofseveral inflammatory mediators, including TNF-α, toll-likereceptor-2 (TLR-2) and TLR-4, in parallel with suppression ofNF-κB signalling and MMP-9 activity, which are key initiatingfactors of atherosclerosis Furthermore, in obese T2DMpatients, 8 week liraglutide treatment is reported to decreaselevels of the inflammatory macrophage activation molecule,sCD163, and pro-inflammatory cytokines, TNF-α and IL-6,while increasing levels of the anti-inflammatory adipokine,

adiponectin (Hogan et al., 2014) Importantly, these clinical

observations are supported by a number of experimentalstudies which have specifically assessed the effects of GLP-1

on development and progression of atherosclerosis Forexample, continuous infusion of exendin-4 in both wild-typeand apolipoprotein E-deficient normoglycaemic mice wasreported to decrease monocyte adhesion and development ofatherosclerotic lesions in thoracic aorta, effects proposed tooccur via cAMP/PKA-dependent suppression of inflammation

(Arakawa et al., 2010) These findings were confirmed by a

different group who demonstrated reduced aortic rophage recruitment, foam cell formation and atheroscleroticlesion development in apolipoprotein E-deficient mice after

mac-GLP-1 infusion (Nagashima et al., 2011) Furthermore,

chemokine-induced migration of CD4+lymphocytes is ited by both GLP-1(7-36) and exendin-4 in a GLP-1 receptor-

inhib-dependent manner (Marx et al., 2010), while liraglutide

suppresses NF-κB signalling in HUVECs and THP-1 monocyteadhesion in human aortic endothelial cells via downstreamactivation of several proinflammatory and cell adhesion mol-ecules, including TNF-α, VCAM-1 and E-selectin (Shiraki

et al., 2012; Krasner et al., 2014) Indeed, liraglutide inhibits

TNF-α in human vascular endothelial cells and reduceshyperglycaemia-mediated PAI-1, ICAM-1 and VCAM-1 acti-vation, which is associated with endothelial dysfunction and

accelerated atherogenesis in T2DM (Liu et al., 2009)

Further-more, the DPP-4 inhibitor, des-fluoro-sitagliptin, is reported

to exert cAMP-dependent anti-inflammatory actions in tured human macrophages by increasing GLP-1 levels and to

Trang 7

cul-reduce atherosclerotic lesion formation in apolipoprotein

E-deficient mice (Matsubara et al., 2012), while alogliptin

inhibits vascular monocyte/macrophage recruitment and

reduces atherosclerotic burden in high-fat diet-fed, LDL

receptor-deficient mice in association with improvement of

metabolic indices (Shah et al., 2011) Taken together, these

experimental data clearly support an important role for

GLP-1 in protecting against vascular inflammation and

atherogenesis, effects which are borne out by the reported

clinical benefits of GLP-1 treatment on circulating

inflamma-tory mediators and CVD biomarkers However, it is evident

that long-term studies specifically investigating effects on

atherosclerotic disease development and progression are

required to ascertain whether the apparent protective effects

of GLP-1 under both normoglycaemic and diabetic

condi-tions may translate to the clinical setting

Angiogenesis

Abnormal angiogenesis is a hallmark of CVD which is

exac-erbated by diabetes, with impaired neovascularization

con-tributing significantly to progression of ischaemic disease

associated with peripheral and coronary arteries

Interest-ingly, it is becoming apparent that GLP-1 may modulate

angiogenesis suggesting that such actions may underlie some

of its reported beneficial cardiovascular effects For example,

exendin-4 stimulates proliferation of human coronary artery

endothelial cells in a GLP-1 receptor-dependent manner via

downstream activation of eNOS, PKA and PI3K/Akt signalling

(Erdogdu et al., 2010) and promotes in vitro HUVEC

migra-tion, ex vivo aortic sprouting angiogenesis and in vivo blood

vessel formation in Matrigel plugs (Kang et al., 2013), while

native GLP-1(7-36) stimulates in vitro angiogenesis in

HUVECs via Akt, Src and PKC-dependent pathways (Aronis

et al., 2013), suggesting that GLP-1 may directly modulate

neovascularization Importantly, these effects appear to

trans-late to the pathological situation, with several recent studies

reporting that GLP-1 can promote the pro-angiogenic actions

of mesenchymal stem cells in different disease settings

Intracoronary artery delivery of GLP-1 eluting encapsulated

human mesenchymal stem cells in a porcine model of

experi-mental myocardial infarction (MI) resulted in improved left

ventricular function and remodelling which was associated

with increased infarct zone angiogenesis (Wright et al., 2012),

while peri-adventitial treatment of porcine vein grafts with

these cells inhibited neointima formation in parallel with

accelerated adventitial angiogenesis (Huang et al., 2013)

Fur-thermore, the addition of GLP-1 to encapsulated human

mes-enchymal cells significantly improved blood flow recovery

and foot salvage in a mouse model of hindlimb ischaemia via

increased capillary and arteriole formation secondary to

par-acrine activation of VEGF-A (Katare et al., 2013) Although

the majority of work investigating the pro-angiogenic actions

of GLP-1 has been performed in normoglycaemic models, a

recent study reported similar beneficial effects in the setting

of diabetes Impaired myocardial angiogenesis in STZ-treated

T1DM rats and associated fibrosis and diastolic dysfunction

were reversed by genetic deletion of DPP-4 or

pharmacologi-cal inhibition with vildagliptin (Shigeta et al., 2012)

Interest-ingly, this study identified DPP-4 as being membrane-bound

and localized to the cardiac capillary endothelium with

increased expression in diabetes, which together with a

report of increased binding affinity of GLP-1 to the coronaryendothelium but not cardiomyocytes in isolated perfused

T1DM rat hearts (Barakat et al., 2011), supports a key

endothelial-specific role of GLP-1 in this setting Althoughthese data provide supportive evidence for pro-angiogenicactions of GLP-1 in diabetes, it is clear that additional mecha-nistic studies are required using different CVD models inorder to define its precise role Furthermore, it is important toassess the effects of GLP-1 therapy in diabetic patients inorder to investigate whether the apparent pro-angiogeniceffects of GLP-1 translate to the clinical setting and are offunctional relevance

GLP-1 and the diabetic myocardium

The heart is one of the major organ targets of GLP-1 and anincreasing number of studies have investigated the actions ofnative GLP-1(7-36), GLP-1 receptor agonists and DPP-4inhibitors in the context of cardioprotection The majority ofexperimental studies have focused on the effects of GLP-1 incardiac ischaemia and its apparent ability to protect againstacute myocardial damage Indeed, it is well established thatGLP-1 pretreatment and chronic DPP-4 inhibition reduceinfarct size after experimental ischaemia in both small andlarge animal models, which is associated with increased sur-

vival and improved cardiac function (Bose et al., 2005; Ban

et al., 2008; 2010; Timmers et al., 2009) Interestingly, a

recent study employing a rabbit model of ischaemia/reperfusion injury reported protective actions of transferrin-stabilized GLP-1, when given both 12 h prior to ischaemiaand immediately upon reperfusion, suggesting that GLP-1may limit infarct size and contractile dysfunction directly,rather than by preconditioning the heart against ischaemia,

as suggested by previous reports (Matsubara et al., 2011) In

addition to its established beneficial actions against acuteischaemic myocardial damage, GLP-1 also confers protectionagainst contractile dysfunction associated with experimentalchronic post-MI remodelling, dilated cardiomyopathy and

hypertensive heart failure (Nikolaidis et al., 2004a; Poornima

et al., 2008; Liu et al., 2010), with similar results reported in

the clinical setting in response to short-term GLP-1 treatment

(Nikolaidis et al., 2004b; Sokos et al., 2006).

Until recently, only limited data were available on thecardiac actions of GLP-1 in diabetes, but it is becomingincreasingly apparent that GLP-1 also plays a key cardiopro-tective role in this setting This is important as it is wellknown that hyperglycaemia is associated with increased sus-ceptibility to cardiac disease and poor outcomes in both

humans and experimental models (Shiomi et al., 2003; Liu

et al., 2005; Greer et al., 2006; Vergès et al., 2007) Chronic

DPP-4 inhibition with linagliptin improves obesity-relateddiastolic dysfunction in insulin-resistant Zucker rats, but has

no effect on cardiomyocyte hypertrophy and fibrosis (Aroor

et al., 2013) Indeed, exendin-4 has been reported to directly

protect isolated rat cardiomyocytes from high induced apoptosis via inhibition of endoplasmic reticulumstress and activation of sarcoplasmic reticulum Ca2 +ATPase 2a

glucose-(Younce et al., 2013) GLP-1 also appears to protect against

diabetic cardiomyopathy, which is defined as cardiac function in the absence of, or disproportionate to, associated

Trang 8

dys-hypertension and CAD and is characterized by marked

colla-gen accumulation and impaired diastolic function (Bugger

and Abel, 2014) Both GLP-1 receptor activation and DPP-4

inhibition attenuate development of cardiac dysfunction,

extracellular matrix remodelling, cardiomyocyte

hypertro-phy and apoptosis in experimental models of T1DM and

T2DM, with various mechanisms proposed including

reduc-tion of lipid accumulareduc-tion, oxidative stress and myocardial

inflammation, and modulation of the MMP-2/tissue inhibitor

of MMP-2 axis, endoplasmic reticulum stress and

microvas-cular barrier function (Shigeta et al., 2012; Liu et al., 2013; Monji et al., 2013; Picatoste et al., 2013; Wang et al., 2013).

Furthermore, it appears that GLP-1 also confers reducing actions in diabetes, which is associated withincreased susceptibility to myocardial ischaemia Forexample, mice made diabetic by a combination of STZ

infarct-Figure 1

Summary of the cardiovascular actions of GLP-1 in diabetes GLP-1 exerts indirect cardiovascular benefits in diabetes secondary to its establishedmetabolic actions and subsequent reduction of cardiovascular risk factors In addition, GLP-1 promotes direct cardiovascular benefits which conferprotection against CVD and heart failure, the latter of which may occur via direct myocardial actions or secondary to reduced hypertension andcoronary atherosclerosis

Trang 9

injection and high-fat feeding and treated with the GLP-1

receptor agonist, liraglutide, prior to coronary artery ligation,

demonstrated reduced infarct development and improved

survival compared with those treated with the

glucose-lowering drug, metformin, suggesting that the observed

effects occurred via direct actions on the heart and not

sec-ondary to reduced blood glucose (Noyan-Ashraf et al., 2009).

Similar cardioprotective effects have been reported with

DPP-4 inhibition in experimental diet-induced obesity

(Huisamen et al., 2013), while the infarct-limiting effects of

exendin-4 in mice with T2DM were shown to be mediated by

cAMP-induced PKA activation (Ye et al., 2013) Interestingly,

it has recently been suggested that the infarct-reducing

actions of DPP-4 inhibitors may be glucose-dependent, as

both sitagliptin and vildagliptin were found to only decrease

infarct size in isolated rat hearts subjected to

ischaemia-reperfusion injury when they were perfused with elevated

glucose concentrations ≥7 mmol L−1, with similar results

observed in vivo in diabetic, but not normoglycaemic rats

(Hausenloy et al., 2013) This raises the intriguing possibility

that glucose-lowering may counteract the cardioprotectiveactions of GLP-1 and explain why several large-scale clinicaltrials focused on intensive glucose control in T2DM havefailed to demonstrate significant cardiovascular benefits

(Giorgino et al., 2013) Furthermore, it appears that at least

part of the observed beneficial actions of DPP-4 inhibitorsagainst ischaemia-reperfusion injury may be mediated by thechemokine, stromal cell-derived factor 1α in a GLP-1-

independent manner (Bromage et al., 2014).

In addition to the experimental data highlighting a tective role for GLP-1 in the diabetic heart, importantly, asmall number of studies have assessed its cardiac actions inpatients with diabetes It has been known for some time thatshort-term GLP-1 treatment exerts beneficial effects in clini-cal heart failure in both normoglycaemic and diabeticpatients For example, in a small number of heart failurepatients (New York Heart Association class III/IV), 5 weekinfusion with GLP-1 plus standard therapy improved left

pro-Figure 2

Proposed mechanisms underlying the reported cardiovascular actions of GLP-1 Although it is well established that GLP-1 exerts several beneficialeffects on the CVS relevant to diabetes, such as reduction of metabolic CVD risk factors, BP modulation, improved vascular function, decreasedatherosclerosis, promotion of angiogenesis and attenuation of adverse cardiac remodelling, the precise mechanisms are yet to be established,although several pathways have been proposed which are the focus of further investigation EC, endothelial cell; ECM, extracellular matrix; SDF,stromal cell-derived factor 1α; SR, sarcoplasmic reticulum

Trang 10

ventricular ejection fraction and myocardial oxygen

con-sumption compared with those receiving standard therapy

alone, effects that were seen in both diabetic and

non-diabetic patients (Sokos et al., 2006) Furthermore, a small

non-randomized trial of 72 h GLP-1 infusion following

primary angioplasty after acute MI led to improved cardiac

function in both non-diabetic and diabetic patients which

was still evident upon 120 day follow-up (Nikolaidis et al.,

2004b) More recently, a larger randomized trial in patients

presenting with ST-segment elevation MI reported that

exenatide infusion for 15 min prior to primary angioplasty

continued until 6 h post-reperfusion resulted in improved

myocardial salvage at 3 months although no functional

ben-efits were observed (Lønborg et al., 2012) Indeed, two current

clinical trials are assessing the potential of using exenatide as

a post-conditioning agent to reduce reperfusion injury

fol-lowing percutaneous coronary intervention (Effect of

Addi-tional Treatment With EXenatide in Patients With an Acute

Myocardial Infarction, the EXAMI trial, NCT01254123;

Phar-macological Postconditioning to Reduce Infarct Size

Follow-ing Primary PCI, POSTCON II, NCT00835848) InterestFollow-ingly,

in patients with left ventricular diastolic dysfunction, DPP-4

activity in the coronary sinus and peripheral circulation is

reported to be negatively correlated with diastolic function

and increased by co-morbid diabetes (Shigeta et al., 2012),

suggesting that reduced GLP-1 levels in diabetes may underlie

the associated cardiac dysfunction Exenatide has also been

found to modulate myocardial glucose transport and uptake

in T2DM patients dependent upon the degree of insulin

resistance (Gejl et al., 2012), although a similar study

reported that GLP-1-induced increases in resting myocardial

glucose uptake in lean individuals were absent in obese

T2DM patients, with parallel studies in pigs suggesting that

this was due to impaired p38-MAPK signalling (Moberly et al.,

2013) Interestingly, a recent experimental study found that

exendin-4 reduced contractile function and was unable to

stimulate glucose utilization in normal rat hearts in the

pres-ence of fatty acids (Nguyen et al., 2013), despite previous

reports of increased myocardial glucose uptake in response to

GLP-1 in experimental myocardial ischaemia and dilated

car-diomyopathy (Nikolaidis et al., 2005; Zhao et al., 2006;

Bhashyam et al., 2010) Such findings highlight the need for

detailed investigation of the effects of GLP-1 on altered

myo-cardial metabolism in diabetic patients both with and

without cardiac complications, in which the effects of GLP-1

may diverge

Although these clinical and experimental data are clearly

supportive of an important role for GLP-1 signalling in the

diabetic heart, they are largely descriptive with limited focus

on underlying mechanisms Previous studies in experimental

models of heart failure have highlighted several pathways

which may mediate the cardioprotective effects of GLP-1,

including cAMP/PKA, PI3K/Akt, p44/p42MAPK, ERK1/2 (Bose

et al., 2005; Timmers et al., 2009; Ravassa et al., 2011),

together with suggestions of GLP-1 receptor-independent

sig-nalling (Nikolaidis et al., 2005; Sonne et al., 2008) However,

the precise mechanisms underlying the apparent protective

actions of GLP-1 in the diabetic heart, in which GLP-1

sig-nalling is likely to be different, remain unknown and clearly

need to be defined in order to fully assess the therapeutic

Trang 11

Summary and future perspective

Over recent years, it has become clear that GLP-1 exerts

important actions on the CVS in both health and disease in

addition to its prototypic effects on glycaemic control (Grieve

et al., 2009) and also confers beneficial effects on the

cardio-vascular risk profile in diabetic patients However, emerging

evidence now strongly suggests that GLP-1 exerts specific

cardiovascular actions in diabetes and may attenuate the

development and progression of associated cardiovascular

complications (summarized in Figure 1), although the precise

mechanisms are yet to be established with several candidate

pathways proposed (see Figure 2) Nonetheless, it is

impor-tant to note that the majority of data pointing towards such

beneficial effects are largely experimental and that equivalent

information on the cardiovascular actions of GLP-1 in the

clinical setting of diabetes is somewhat lacking, particularly

in relation to its chronic effects In this regard, the first

large-scale GLP-1 clinical trials to assess cardiovascular

out-comes after long-term treatment (SAVOR-TIMI 53, EXAMINE)

have recently reported that chronic DPP-4 inhibition with

either saxagliptin or apogliptin had no significant effects on

their primary composite end points of cardiovascular death,

or non-fatal MI/stroke (Scirica et al., 2013; White et al., 2013),

although it should be noted that SAVOR-TIMI 53 reported a

27% increase in hospitalization for heart failure However,

until the results of several ongoing clinical trials investigating

the chronic cardiovascular effects of GLP-1 receptor agonists

are known (summarized in Table 1 together with further

DPP-4 inhibitor trials), in which circulating GLP-1 levels will

be much higher than those achieved using DPP-4 inhibitors,

no conclusions can be drawn on either the potential clinical

cardiovascular benefits or safety of GLP-1-based therapies in

diabetes Nonetheless, the apparent complexity of

cardiovas-cular GLP-1 signalling under both normal and diabetic

con-ditions clearly suggests that it is likely that selective targeting

of specific aspects of CVD may be required in order to realize

the optimal benefits of GLP-1 targeting in this setting

Acknowledgements

The authors’ work is supported by the British Heart

Founda-tion, Diabetes UK and the Medical Research Council

Conflict of interest

None

References

Action to Control Cardiovascular Risk in Diabetes Study Group

(2008) Effects of intensive glucose lowering in type 2 diabetes N

Engl J Med 358: 2545–2559

Alexander SPH, Benson HE, Faccenda E, Pawson AJ, Sharman JL,

Spedding M et al (2013a) The Concise Guide to PHARMACOLOGY

2013/14: G protein-coupled receptors Br J Pharmacol 170:

1459–1581

Alexander SPH, Benson HE, Faccenda E, Pawson AJ, Sharman JL,

Spedding M et al (2013b) The Concise Guide to PHARMACOLOGY

2013/14: Ion channels Br J Pharmacol 170: 1607–1651

Alexander SPH, Benson HE, Faccenda E, Pawson AJ, Sharman JL,

Spedding M et al (2013c) The Concise Guide to PHARMACOLOGY

2013/14: Catalytic receptors Br J Pharmacol 170: 1607–1651.Alexander SPH, Benson HE, Faccenda E, Pawson AJ, Sharman JL,

Spedding M et al (2013d) The Concise Guide to PHARMACOLOGY

2013/14:Transporters Br J Pharmacol 170: 1676–1705

Alexander SPH, Benson HE, Faccenda E, Pawson AJ, Sharman JL,

Spedding M et al (2013e) The Concise Guide to PHARMACOLOGY

2013/14: Enzymes Br J Pharmacol 170: 1797–1867

Amori RE, Lau J, Pittas AG (2007) Efficacy and safety of incretintherapy in type 2 diabetes: systematic review and meta-analysis.JAMA 298: 194–206

Arakawa M, Mita T, Azuma K, Ebato C, Goto H, Nomiyama T et al.

(2010) Inhibition of monocyte adhesion to endothelial cells andattenuation of atherosclerotic lesion by a glucagon-like peptide-1receptor agonist, exendin-4 Diabetes 59: 1030–1037

Aronis KN, Chamberland JP, Mantzoros CS (2013) GLP-1 promotesangiogenesis in human endothelial cells in a dose-dependentmanner, through the Akt, Src and PKC pathways Metabolism 62:1279–1286

Aroor AR, Sowers JR, Bender SB, Nistala R, Garro M, Mugerfeld I

et al (2013) Dipeptidylpeptidase inhibition is associated with

improvement in blood pressure and diastolic function ininsulin-resistant male Zucker obese rats Endocrinology 154:2501–2513

Aroor AR, Sowers JR, Jia G, DeMarco VG (2014) Pleiotropic effects

of the dipeptidylpeptidase-4 inhibitors on the cardiovascularsystem Am J Physiol Heart Circ Physiol 307: H477–H492

Astrup A, Rössner S, Van Gaal L, Rissanen A, Niskanen L, Al Hakim

M et al (2009) Effects of liraglutide in the treatment of obesity: a

randomised, double-blind, placebo-controlled study Lancet 374:1606–1616

Astrup A, Carraro R, Finer N, Harper A, Kunesova M, Lean M et al.

(2012) Safety, tolerability and sustained weight loss over 2 yearswith the once-daily human GLP-1 analog, liraglutide Int J Obes(Lond) 36: 843–854

Ayaori M, Iwakami N, Uto-Kondo H, Sato H, Sasaki M, Komatsu T

et al (2013) Dipeptidyl peptidase-4 inhibitors attenuate endothelial

function as evaluated by flow-mediated vasodilatation in type 2diabetic patients J Am Heart Assoc 2: e003277

Ban K, Noyan-Ashraf MH, Hoefer J, Bolz S, Drucker DJ, Husain M(2008) Cardioprotective and vasodilatory actions of glucagon-likepeptide 1 receptor are mediated through both glucagon-like peptide

1 receptor-dependent and -independent pathways Circulation 117:2340–2350

Ban K, Kim K, Cho C, Sauvé M, Diamandis EP, Backx PH et al.

(2010) Glucagon-like peptide (GLP)-1 (9-36) amide-mediatedcytoprotection is blocked by exendin (9-39) yet does not requirethe known GLP-1 receptor Endocrinology 151: 1520–1531.Barakat GM, Nuwayri-Salti N, Kadi LN, Bitar KM, Al-Jaroudi WA,Bikhazi AB (2011) Role of glucagon-like peptide-1 and its agonists

on early prevention of cardiac remodeling in type 1 diabetic rathearts Gen Physiol Biophys 30: 34–44

Barragán J, Rodríguez R, Blázquez E (1994) Changes in arterialblood pressure and heart rate induced by glucagon-likepeptide-1-(7-36) amide in rats Am J Physiol Endocrinol Metab 266:E459–E466

Trang 12

Barragán JM, Rodriguez RE, Eng J, Blázquez E (1996) Interactions of

exendin-(9-39) with the effects of glucagon-like peptide-1-(7-36)

amide and of exendin-4 on arterial blood pressure and heart rate in

rats Regul Pept 67: 63–68

Basu A, Charkoudian N, Schrage W, Rizza RA, Basu R, Joyner MJ

(2007) Beneficial effects of GLP-1 on endothelial function in

humans: dampening by glyburide but not by glimepiride Am J

Physiol Endocrinol Metab 293: E1289–E1295

Bergenstal RM, Wysham C, MacConell L, Malloy J, Walsh B, Yan P

et al (2010) Efficacy and safety of exenatide once weekly versus

sitagliptin or pioglitazone as an adjunct to metformin for treatment

of type 2 diabetes (DURATION-2): a randomised trial Lancet 376:

431–439

Bertoni AG, Hundley WG, Massing MW, Bonds DE, Burke GL, Goff

DC (2004) Heart failure prevalence, incidence, and mortality in the

elderly with diabetes Diabetes Care 27: 699–703

Bhashyam S, Fields AV, Patterson B, Testani JM, Chen L, Shen Y

et al (2010) Glucagon-like peptide-1 increases myocardial glucose

uptake via p38alpha MAP kinase-mediated, nitric oxide-dependent

mechanisms in conscious dogs with dilated cardiomyopathy Circ

Heart Fail 3: 512–521

Bose AK, Mocanu MM, Carr RD, Brand CL, Yellon DM (2005)

Glucagon-like peptide 1 can directly protect the heart against

ischemia/reperfusion injury Diabetes 54: 146–151

Bromage DI, Davidson SM, Yellon DM (2014) Stromal derived

factor 1α: a chemokine that delivers a two-pronged defence of the

myocardium Pharmacol Ther 143: 305–315

Bugger H, Abel ED (2014) Molecular mechanisms of diabetic

cardiomyopathy Diabetologia 57: 660–671

Bunck MC, Diamant M, Eliasson B, Cornér A, Shaginian RM, Heine

RJ et al (2010) Exenatide affects circulating cardiovascular risk

biomarkers independently of changes in body composition

Diabetes Care 33: 1734–1737

Buse JB, Rosenstock J, Sesti G, Schmidt WE, Montanya E, Brett JH

et al (2009) Liraglutide once a day versus exenatide twice a day for

type 2 diabetes: a 26-week randomised, parallel-group,

multinational, open-label trial (LEAD-6) Lancet 374: 39–47

Ceriello A, Novials A, Ortega E, Canivell S, La Sala L, Pujadas G

et al (2013) Glucagon-like peptide 1 reduces endothelial

dysfunction, inflammation, and oxidative stress induced by both

hyperglycemia and hypoglycemia in type 1 diabetes Diabetes Care

36: 2346–2350

Chai W, Dong Z, Wang N, Wang W, Tao L, Cao W et al (2012).

Glucagon-like peptide 1 recruits microvasculature and increases

glucose use in muscle via a nitric oxide-dependent mechanism

Diabetes 61: 888–896

Chaudhuri A, Ghanim H, Vora M, Sia CL, Korzeniewski K, Dhindsa

S et al (2011) Exenatide exerts a potent antiinflammatory effect.

J Clin Endocrinol Metab 97: 198–207

Courrèges J, Vilsbøll T, Zdravkovic M, Le-Thi T, Krarup T, Schmitz

O et al (2008) Beneficial effects of once-daily liraglutide, a human

glucagon-like peptide-1 analogue, on cardiovascular risk biomarkers

in patients with Type 2 diabetes Diabet Med 25: 1129–1131

Deacon CF, Nauck MA, Toft-Nielsen M, Pridal L, Willms B, Holst JJ

(1995) Both subcutaneously and intravenously administered

glucagon-like peptide I are rapidly degraded from the NH2-terminus

in type II diabetic patients and in healthy subjects Diabetes 44:

1126–1131

Diamant M, Van Gaal L, Stranks S, Northrup J, Cao D, Taylor K

et al (2010) Once weekly exenatide compared with insulin glargine

titrated to target in patients with type 2 diabetes (DURATION-3): anopen-label randomised trial Lancet 375: 2234–2243

Donnelly D (2012) The structure and function of the glucagon-likepeptide-1 receptor and its ligands Br J Pharmacol 166: 27–41

Drucker DJ, Philippe J, Mojsov S, Chick WL, Habener JF (1987).Glucagon-like peptide I stimulates insulin gene expression andincreases cyclic AMP levels in a rat islet cell line Proc Natl Acad Sci

U S A 84: 3434–3438

Drucker DJ, Buse JB, Taylor K, Kendall DM, Trautmann M, Zhuang

D et al (2008) Exenatide once weekly versus twice daily for the

treatment of type 2 diabetes: a randomised, open-label,non-inferiority study Lancet 372: 1240–1250

Duckworth W, Abraira C, Moritz T, Reda D, Emanuele N, Reaven

PD et al (2009) Glucose control and vascular complications in

veterans with type 2 diabetes N Engl J Med 360: 129–139

Erdogdu Ö, Nathanson D, Sjöholm Å, Nyström T, Zhang Q (2010).Exendin-4 stimulates proliferation of human coronary arteryendothelial cells through eNOS-, PKA- and PI3K/Akt-dependentpathways and requires GLP-1 receptor Mol Cell Endocrinol 325:26–35

Flint A, Raben A, Astrup A, Holst JJ (1998) Glucagon-like peptide 1promotes satiety and suppresses energy intake in humans J ClinInvest 101: 515–520

Flock G, Baggio LL, Longuet C, Drucker DJ (2007) Incretinreceptors for glucagon-like peptide 1 and glucose-dependentinsulinotropic polypeptide are essential for the sustained metabolicactions of vildagliptin in mice Diabetes 56: 3006–3013

Forst T, Michelson G, Ratter F, Weber M, Anders S, Mitry M et al.

(2012) Addition of liraglutide in patients with Type 2 diabetes wellcontrolled on metformin monotherapy improves several markers ofvascular function Diabet Med 29: 1115–1118

Fukuda-Tsuru S, Anabuki J, Abe Y, Yoshida K, Ishii S (2012) Anovel, potent, and long-lasting dipeptidyl peptidase-4 inhibitor,teneligliptin, improves postprandial hyperglycemia anddyslipidemia after single and repeated administrations Eur JPharmacol 696: 194–202

Gallwitz B, Vaag A, Falahati A, Madsbad S (2010) Adding liraglutide

to oral antidiabetic drug therapy: onset of treatment effects overtime Int J Clin Pract 64: 267–276

Garber A, Henry R, Ratner R, Garcia-Hernandez PA, Rodriguez-Pattzi

H, Olvera-Alvarez I et al (2009) Liraglutide versus glimepiride

monotherapy for type 2 diabetes (LEAD-3 Mono): a randomised,52-week, phase III, double-blind, parallel-treatment trial Lancet373: 473–481

Gardiner S, March J, Kemp P, Bennett T (2008) Autonomic nervoussystem-dependent and -independent cardiovascular effects ofexendin-4 infusion in conscious rats Br J Pharmacol 154: 60–71

Gardiner S, March J, Kemp P, Bennett T, Baker D (2010) Possibleinvolvement of GLP-1 (9-36) in the regional haemodynamic effects

of GLP-1 (7-36) in conscious rats Br J Pharmacol 161: 92–102

Gaspari T, Liu H, Welungoda I, Hu Y, Widdop RE, Knudsen LB et al.

(2011) A GLP-1 receptor agonist liraglutide inhibits endothelial celldysfunction and vascular adhesion molecule expression in anApoE-/-mouse model Diab Vasc Dis Res 8: 117–124

Gejl M, Søndergaard H, Stecher C, Bibby BM, Møller N, Bøtker H

et al (2012) Exenatide alters myocardial glucose transport and

uptake depending on insulin resistance and increases myocardialblood flow in patients with type 2 diabetes J Clin EndocrinolMetab 97: E1165–E1169

Trang 13

Gill A, Hoogwerf BJ, Burger J, Bruce S, MacConell L, Yan P et al.

(2010) Effect of exenatide on heart rate and blood pressure in

subjects with type 2 diabetes mellitus: a double-blind,

placebo-controlled, randomized pilot study Cardiovasc Diabetol 9:

6

Ginsberg HN (2011) The ACCORD (Action to Control

Cardiovascular Risk in Diabetes) Lipid trial: what we learn from

subgroup analyses Diabetes Care 34 (Suppl 2): S107–S108

Giorgino F, Leonardini A, Laviola L (2013) Cardiovascular disease

and glycemic control in type 2 diabetes: now that the dust is

settling from large clinical trials Ann N Y Acad Sci 1281: 36–50

Golpon HA, Puechner A, Welte T, Wichert PV, Feddersen CO

(2001) Vasorelaxant effect of glucagon-like peptide-(7-36) amide

and amylin on the pulmonary circulation of the rat Regul Pept

102: 81–86

Goyal S, Kumar S, Bijjem KV, Singh M (2010) Role of glucagon-like

peptide-1 in vascular endothelial dysfunction Indian J Exp Biol 48:

61–69

Green B, Mooney M, Gault V, Irwin N, Bailey C, Harriott P et al.

(2004) Lys9 for Glu9 substitution in glucagon-like peptide-1 (7-36)

amide confers dipeptidyl peptidase IV resistance with cellular and

metabolic actions similar to those of established antagonists

glucagon-like peptide-1 (9-36) amide and exendin (9-39)

Metabolism 53: 252–259

Green BD, Hand KV, Dougan JE, McDonnell BM, Cassidy RS,

Grieve DJ (2008) GLP-1 and related peptides cause

concentration-dependent relaxation of rat aorta through a pathway

involving KATP and cAMP Arch Biochem Biophys 478: 136–142

Greer JJ, Ware DP, Lefer DJ (2006) Myocardial infarction and heart

failure in the db/db diabetic mouse Am J Physiol Heart Circ

Physiol 290: H146–H153

Grieve DJ, Cassidy RS, Green BD (2009) Emerging cardiovascular

actions of the incretin hormone glucagon-like peptide-1: potential

therapeutic benefits beyond glycaemic control? Br J Pharmacol 157:

1340–1351

Gustavson S, Chen D, Somayaji V, Hudson K, Baltrukonis D, Singh

J et al (2011) Effects of a long-acting GLP-1 mimetic (PF-04603629)

on pulse rate and diastolic blood pressure in patients with type 2

diabetes mellitus Diabetes Obes Metab 13: 1056–1058

Gutzwiller J, Drewe J, Göke B, Schmidt H, Rohrer B, Lareida J et al.

(1999) Glucagon-like peptide-1 promotes satiety and reduces food

intake in patients with diabetes mellitus type 2 Am J Physiol Regul

Integr Comp Physiol 276: R1541–R1544

Haffner SM (2006) The metabolic syndrome: inflammation,

diabetes mellitus, and cardiovascular disease Am J Cardiol 97:

3–11

Halbirk M, Nørrelund H, Møller N, Holst JJ, Schmitz O, Nielsen R

et al (2010) Cardiovascular and metabolic effects of 48-h

glucagon-like peptide-1 infusion in compensated chronic patients

with heart failure Am J Physiol Heart Circ Physiol 298:

H1096–H1102

Han SZ, Ouchi Y, Karaki H, Orimo H (1995) Inhibitory effects of

insulin on cytosolic Ca2+ level and contraction in the rat aorta

endothelium-dependent and -independent mechanisms Circ Res

77: 673–678

Hattori S (2010) Sitagliptin reduces albuminuria in patients with

type 2 diabetes Endocr J 58: 69–73

Hausenloy DJ, Whittington HJ, Wynne AM, Begum SS, Theodorou

L, Riksen N et al (2013) Dipeptidyl peptidase-4 inhibitors and

GLP-1 reduce myocardial infarct size in a glucose-dependentmanner Cardiovasc Diabetol 12: 154

Hein GJ, Baker C, Hsieh J, Farr S, Adeli K (2013) GLP-1 and GLP-2

as yin and yang of intestinal lipoprotein production evidence forpredominance of GLP-2-stimulated postprandial lipemia in normaland insulin-resistant states Diabetes 62: 373–381

Hirata K, Kume S, Araki S, Sakaguchi M, Chin-Kanasaki M, Isshiki K

et al (2009) Exendin-4 has an anti-hypertensive effect in

salt-sensitive mice model Biochem Biophys Res Commun 380:44–49

Hogan AE, Gaoatswe G, Lynch L, Corrigan MA, Woods C,

O’Connell J et al (2014) Glucagon-like peptide 1 analogue therapy

directly modulates innate immune-mediated inflammation inindividuals with type 2 diabetes mellitus Diabetologia 57: 781–784

Holman RR, Paul SK, Bethel MA, Matthews DR, Neil HA (2008).10-year follow-up of intensive glucose control in type 2 diabetes

N Engl J Med 359: 1577–1589

Holst J, Schwartz T, Lovgreen N, Pedersen O, Beck-Nielsen H(1982) Diurnal profile of pancreatic polypeptide, pancreaticglucagon, gut glucagon and insulin in human morbid obesity Int JObes 7: 529–538

Hopkins N, Cuthbertson D, Kemp G, Pugh C, Green D, Cable N

et al (2013) Effects of 6 months glucagon-like peptide-1 receptor

agonist treatment on endothelial function in type 2 diabetesmellitus patients Diabetes Obes Metab 15: 770–773

Horváth E, Benko R, Kiss L, Murányi M, Pék T, Fekete K et al.

(2009) Rapid ‘glycaemic swings’ induce nitrosative stress, activatepoly (ADP-ribose) polymerase and impair endothelial function in arat model of diabetes mellitus Diabetologia 52: 952–961

Huang W, Newby GB, Lewis AL, Stratford PW, Rogers CA, Newby

AC et al (2013) Periadventitial human stem cell treatment reduces

vein graft intimal thickening in pig vein-into-artery interpositiongrafts J Surg Res 183: 33–39

Hubert HB, Feinleib M, McNamara PM, Castelli WP (1983) Obesity

as an independent risk factor for cardiovascular disease: a 26-yearfollow-up of participants in the Framingham Heart Study

Circulation 67: 968–977

Huisamen B, George C, Dietrich D, Genade S (2013)

Cardioprotective and anti-hypertensive effects of Prosopis glandulosa

in rat models of pre-diabetes: cardiovascular topics Cardiovasc J Afr24: 10–16

International Diabetes Federation (2014) IDF Diabetes Atlas SixthEdition Available at: http://www.idf.org/diabetesatlas (accessed5/25/2014)

Irace C, De Luca S, Shehaj E, Carallo C, Loprete A, Scavelli F et al.

(2013) Exenatide improves endothelial function assessed by flowmediated dilation technique in subjects with type 2 diabetes:results from an observational research Diab Vasc Dis Res 10: 72–77

Kahn AM, Husid A, Odebunmi T, Allen JC, Seidel CL, Song T(1998) Insulin inhibits vascular smooth muscle contraction at asite distal to intracellular Ca2+ concentration Am J PhysiolEndocrinol Metab 274: E885–E892

Kang H, Kang Y, Chun HJ, Jeong J, Park C (2013) Evaluation of the

in vitro and in vivo angiogenic effects of exendin-4 BiochemBiophys Res Commun 434: 150–154

Katare R, Riu F, Rowlinson J, Lewis A, Holden R, Meloni M et al.

(2013) Perivascular delivery of encapsulated mesenchymal stemcells improves postischemic angiogenesis via paracrine activation ofVEGF-A Arterioscler Thromb Vasc Biol 33: 1872–1880

Trang 14

Kelly AS, Bergenstal RM, Gonzalez-Campoy JM, Katz H, Bank AJ

(2012) Effects of exenatide vs metformin on endothelial function

in obese patients with pre-diabetes: a randomized trial Cardiovasc

Diabetol 11: 64

Kim M, Platt MJ, Shibasaki T, Quaggin SE, Backx PH, Seino S et al.

(2013) GLP-1 receptor activation and Epac2 link atrial natriuretic

peptide secretion to control of blood pressure Nat Med 19:

567–575

Klonoff DC, Buse JB, Nielsen LL, Guan X, Bowlus CL, Holcombe JH

et al (2007) Exenatide effects on diabetes, obesity, cardiovascular

risk factors and hepatic biomarkers in patients with type 2 diabetes

treated for at least 3 years Curr Med Res Opin 24: 275–286

Koska J, Schwartz EA, Mullin MP, Schwenke DC, Reaven PD (2010)

Improvement of postprandial endothelial function after a single

dose of exenatide in individuals with impaired glucose tolerance

and recent-onset type 2 diabetes Diabetes Care 33: 1028–1030

Kothare PA, Linnebjerg H, Isaka Y, Uenaka K, Yamamura A, Yeo KP

et al (2008) Pharmacokinetics, pharmacodynamics, tolerability,

and safety of exenatide in Japanese patients with type 2 diabetes

mellitus J Clin Pharmacol 48: 1389–1399

Krasner NM, Ido Y, Ruderman NB, Cacicedo JM (2014)

Glucagon-like peptide-1 (GLP-1) analog liraglutide inhibits

endothelial cell inflammation through a calcium and AMPK

dependent mechanism PLoS ONE 9: e97554

Kreymann B, Ghatei M, Williams G, Bloom S (1987) Glucagon-like

peptide-1 7–36: a physiological incretin in man Lancet 330:

1300–1304

Liu H, Dear AE, Knudsen LB, Simpson RW (2009) A long-acting

glucagon-like peptide-1 analogue attenuates induction of

plasminogen activator inhibitor type-1 and vascular adhesion

molecules J Endocrinol 201: 59–66

Liu J, Liu Y, Chen L, Wang Y, Li J (2013) Glucagon-like peptide-1

analog liraglutide protects against diabetic cardiomyopathy by the

inhibition of the endoplasmic reticulum stress pathway J Diabetes

Res 2013: 630537

Liu Q, Anderson C, Broyde A, Polizzi C, Fernandez R, Baron A et al.

(2010) Glucagon-like peptide-1 and the exenatide analogue

AC3174 improve cardiac function, cardiac remodeling, and survival

in rats with chronic heart failure Cardiovasc Diabetol 9: 76

Liu X, Wei J, Peng DH, Layne MD, Yet SF (2005) Absence of heme

oxygenase-1 exacerbates myocardial ischemia/reperfusion injury in

diabetic mice Diabetes 54: 778–784

Lønborg J, Vejlstrup N, Kelbæk H, Bøtker HE, Kim WY, Mathiasen

AB et al (2012) Exenatide reduces reperfusion injury in patients

with ST-segment elevation myocardial infarction Eur Heart J 33:

1491–1499

Madsen AN, Hansen G, Paulsen SJ, Lykkegaard K, Tang-Christensen

M, Hansen HS et al (2010) Long-term characterization of the

diet-induced obese and diet-resistant rat model: a polygenetic rat

model mimicking the human obesity syndrome J Endocrinol 206:

287–296

Marx N, Burgmaier M, Heinz P, Ostertag M, Hausauer A, Bach H

et al (2010) Glucagon-like peptide-1 (1-37) inhibits

chemokine-induced migration of human CD4-positive

lymphocytes Cell Mol Life Sci 67: 3549–3555

Matikainen N, Mänttäri S, Schweizer A, Ulvestad A, Mills D,

Dunning B et al (2006) Vildagliptin therapy reduces postprandial

intestinal triglyceride-rich lipoprotein particles in patients with type

2 diabetes Diabetologia 49: 2049–2057

Matsubara J, Sugiyama S, Sugamura K, Nakamura T, Fujiwara Y,

Akiyama E et al (2012) A dipeptidyl peptidase-4 inhibitor,

des-fluoro-sitagliptin, improves endothelial function and reducesatherosclerotic lesion formation in apolipoprotein E-deficient mice

J Am Coll Cardiol 59: 265–276

Matsubara M, Kanemoto S, Leshnower BG, Albone EF, Hinmon R,

Plappert T et al (2011) Single dose GLP-1-Tf ameliorates

myocardial ischemia/reperfusion injury J Surg Res 165: 38–45.Moberly SP, Mather KJ, Berwick ZC, Owen MK, Goodwill AG,

Casalini ED et al (2013) Impaired cardiometabolic responses to

glucagon-like peptide 1 in obesity and type 2 diabetes mellitus.Basic Res Cardiol 108: 365

Monji A, Mitsui T, Bando YK, Aoyama M, Shigeta T, Murohara T(2013) Glucagon-like peptide-1 receptor activation reverses cardiacremodeling via normalizing cardiac steatosis and oxidative stress intype 2 diabetes Am J Physiol Heart Circ Physiol 305: H295–H304.Moretto TJ, Milton DR, Ridge TD, MacConell LA, Okerson T, Wolka

AM et al (2008) Efficacy and tolerability of exenatide monotherapy

over 24 weeks in antidiabetic drug-naive patients with type 2diabetes: a randomized, double-blind, placebo-controlled,parallel-group study Clin Ther 30: 1448–1460

Morinigo R, Moizé V, Musri M, Lacy AM, Navarro S, Marín JL et al.

(2006) Glucagon-like peptide-1, peptide YY, hunger, and satietyafter gastric bypass surgery in morbidly obese subjects J ClinEndocrinol Metab 91: 1735–1740

Nagashima M, Watanabe T, Terasaki M, Tomoyasu M, Nohtomi K,

Kim-Kaneyama J et al (2011) Native incretins prevent the

development of atherosclerotic lesions in apolipoprotein Eknockout mice Diabetologia 54: 2649–2659

Nakano T, Nakajima K, Niimi M, Fujita MQ, Nakajima Y, Takeichi S

et al (2008) Detection of apolipoproteins B-48 and B-100 carrying

particles in lipoprotein fractions extracted from human aorticatherosclerotic plaques in sudden cardiac death cases Clin ChimActa 390: 38–43

Nathan DM (1996) The pathophysiology of diabetic complications:how much does the glucose hypothesis explain? Ann Intern Med124: 86–89

Nathanson D, Erdogdu Ö, Pernow J, Zhang Q, Nyström T (2009).Endothelial dysfunction induced by triglycerides is not restored byexenatide in rat conduit arteries ex vivo Regul Pept 157: 8–13.Nauck M, Frid A, Hermansen K, Shah NS, Tankova T, Mitha IH

et al (2009) Efficacy and safety comparison of liraglutide,

glimepiride, and placebo, all in combination with metformin, intype 2 diabetes: the LEAD (liraglutide effect and action indiabetes)-2 study Diabetes Care 32: 84–90

Nauck M, Frid A, Hermansen K, Thomsen A, During M, Shah N

et al (2013) Long-term efficacy and safety comparison of

liraglutide, glimepiride and placebo, all in combination withmetformin in type 2 diabetes: 2-year results from the LEAD-2 study.Diabetes Obes Metab 15: 204–212

Nauck MA, Homberger E, Siegel EG, Allen RC, Eaton RP, Ebert R

et al (1986) Incretin effects of increasing glucose loads in man

calculated from venous insulin and c-peptide responses J ClinEndocrinol Metab 63: 492–498

Nauck MA, Niedereichholz U, Ettler R, Holst JJ, Orskov C, Ritzel R

et al (1997) Glucagon-like peptide 1 inhibition of gastric emptying

outweighs its insulinotropic effects in healthy humans Am JPhysiol Endocrinol Metab 273: E981–E988

Näslund E, Gutniak M, Skogar S, Rössner S, Hellström PM (1998a).Glucagon-like peptide 1 increases the period of postprandial satietyand slows gastric emptying in obese men Am J Clin Nutr 68:525–530

Trang 15

Näslund E, Grybäck P, Backman L, Jacobsson H, Juul J,

Theodorsson HE et al (1998b) Distal small bowel hormones:

correlation with fasting antroduodenal motility and gastric

emptying Dig Dis Sci 43: 945–952

Neter JE, Stam BE, Kok FJ, Grobbee DE, Geleijnse JM (2003)

Influence of weight reduction on blood pressure a meta-analysis of

randomized controlled trials Hypertension 42: 878–884

Nguyen TD, Shingu Y, Amorim PA, Schwarzer M, Doenst T (2013)

Glucagon-like peptide-1 reduces contractile function and fails to

boost glucose utilization in normal hearts in the presence of fatty

acids Int J Cardiol 168: 4085–4092

Nikolaidis LA, Elahi D, Hentosz T, Doverspike A, Huerbin R,

Zourelias L et al (2004a) Recombinant glucagon-like peptide-1

increases myocardial glucose uptake and improves left ventricular

performance in conscious dogs with pacing-induced dilated

cardiomyopathy Circulation 110: 955–961

Nikolaidis LA, Mankad S, Sokos GG, Miske G, Shah A, Elahi D et al.

(2004b) Effects of glucagon-like peptide-1 in patients with acute

myocardial infarction and left ventricular dysfunction after

successful reperfusion Circulation 109: 962–965

Nikolaidis LA, Elahi D, Shen Y-T, Shannon RP (2005) Active

metabolite of GLP-1 mediates myocardial glucose uptake and

improves left ventricular performance in conscious dogs with

dilated cardiomyopathy Am J Physiol Heart Circ Physiol 289:

H2401–H2408

Noyan-Ashraf MH, Momen MA, Ban K, Sadi A, Zhou Y, Riazi AM

et al (2009) GLP-1R agonist liraglutide activates cytoprotective

pathways and improves outcomes after experimental myocardial

infarction in mice Diabetes 58: 975–983

Nyström T, Gutniak MK, Zhang Q, Zhang F, Holst JJ, Ahrén B et al.

(2004) Effects of glucagon-like peptide-1 on endothelial function in

type 2 diabetes patients with stable coronary artery disease Am J

Physiol Endocrinol Metab 287: E1209–E1215

Nyström T, Gonon AT, Sjöholm A, Pernow J (2005) Glucagon-like

peptide-1 relaxes rat conduit arteries via an

endothelium-independent mechanism Regul Pept 125: 173–177

Okerson T, Yan P, Stonehouse A, Brodows R (2010) Effects of

exenatide on systolic blood pressure in subjects with type 2

diabetes Am J Hypertens 23: 334–339

Özyazgan S, Kutluata N, Afsar S, Özdas S, Akkan A (2005) Effect of

glucagon-like peptide-1 (7-36) and exendin-4 on the vascular

reactivity in streptozotocin/nicotinamide-induced diabetic rats

Pharmacology 74: 119–126

Pabreja K, Mohd M, Koole C, Wootten D, Furness S (2013)

Molecular mechanisms underlying physiological and receptor

pleiotropic effects mediated by GLP-1R activation Br J Pharmacol

171: 1114–1128

Panjwani N, Mulvihill EE, Longuet C, Yusta B, Campbell JE, Brown

TJ et al (2012) GLP-1 receptor activation indirectly reduces hepatic

lipid accumulation but does not attenuate development of

atherosclerosis in diabetic male ApoE(-/-) mice Endocrinology 154:

127–139

Parlevliet ET, Wang Y, Geerling JJ, Schröder-Van der Elst JP, Picha

K, O’Neil K et al (2012) GLP-1 receptor activation inhibits VLDL

production and reverses hepatic steatosis by decreasing hepatic

lipogenesis in high-fat-fed APOE*3-Leiden mice PLoS ONE 7:

e49152

Pawson AJ, Sharman JL, Benson HE, Faccenda E, Alexander SP,

Buneman OP et al.; NC-IUPHAR (2014) The IUPHAR/BPS Guide to

PHARMACOLOGY: an expert-driven knowledgebase of drug targetsand their ligands Nucl Acids Res 42 (Database Issue):

D1098–D1106

Picatoste B, Ramirez E, Caro-Vadillo A, Iborra C, Egido J, Tuñón J

et al (2013) Sitagliptin reduces cardiac apoptosis, hypertrophy and

fibrosis primarily by insulin-dependent mechanisms inexperimental type-II diabetes Potential roles of GLP-1 isoforms.PLoS ONE 8: e78330

Piotrowski K, Becker M, Zugwurst J, Biller-Friedmann I, Spoettl G,

Greif M et al (2013) Circulating concentrations of GLP-1 are

associated with coronary atherosclerosis in humans CardiovascDiabetol 12: 117

Poornima I, Brown SB, Bhashyam S, Parikh P, Bolukoglu H,Shannon RP (2008) Chronic glucagon-like peptide-1 infusionsustains left ventricular systolic function and prolongs survival inthe spontaneously hypertensive, heart failure-prone rat Circ HeartFail 1: 153–160

Pyke C, Heller RS, Kirk RK, Ørskov C, Reedtz-Runge S, Kaastrup P

et al (2014) GLP-1 receptor localization in monkey and human

tissue: novel distribution revealed with extensively validatedmonoclonal antibody Endocrinology 155: 1280–1290

Rask E, Olsson T, Söderberg S, Johnson O, Seckl J, Holst JJ et al.

(2001) Impaired incretin response after a mixed meal is associatedwith insulin resistance in nondiabetic men Diabetes Care 24:1640–1645

Ravassa S, Zudaire A, Carr RD, Diez J (2011) Antiapoptotic effects

of GLP-1 in murine HL-1 cardiomyocytes Am J Physiol Heart CircPhysiol 300: H1361–H1372

Reiner Z, Catapano AL, De Backer G, Graham I, Taskinen M,

Wiklund O et al (2011) ESC/EAS Guidelines for the management

of dyslipidaemias: the Task Force for the management ofdyslipidaemias of the European Society of Cardiology (ESC) and theEuropean Atherosclerosis Society (EAS) Eur Heart J 32: 1769–1818.Richards P, Parker HE, Adriaenssens AE, Hodgson JM, Cork SC,

Trapp S et al (2014) Identification and characterization of GLP-1

receptor-expressing cells using a new transgenic mouse model.Diabetes 63: 1224–1233

Richter G, Feddersen O, Wagner U, Barth P, Goke R, Goke B (1993).GLP-1 stimulates secretion of macromolecules from airways andrelaxes pulmonary artery Am J Physiol Lung Cell Mol Physiol 265:L374–L381

Scheen AJ (2013) Cardiovascular effects of gliptins Nat Rev Cardiol10: 73–84

Schwartz EA, Koska J, Mullin MP, Syoufi I, Schwenke DC, Reaven

PD (2010) Exenatide suppresses postprandial elevations in lipidsand lipoproteins in individuals with impaired glucose tolerance andrecent onset type 2 diabetes mellitus Atherosclerosis 212: 217–222.Scirica BM, Bhatt DL, Braunwald E, Steg PG, Davidson J, Hirshberg

B et al (2013) Saxagliptin and cardiovascular outcomes in patients

with type 2 diabetes mellitus N Engl J Med 369: 1317–1326.Scott R, Wu M, Sanchez M, Stein P (2007) Efficacy and tolerability

of the dipeptidyl peptidase-4 inhibitor sitagliptin as monotherapyover 12 weeks in patients with type 2 diabetes Int J Clin Pract 61:171–180

Shah Z, Kampfrath T, Deiuliis JA, Zhong J, Pineda C, Ying Z et al.

(2011) Long-term dipeptidyl-peptidase 4 inhibition reducesatherosclerosis and inflammation via effects on monocyterecruitment and chemotaxis Circulation 124: 2338–2349

Shigeta T, Aoyama M, Bando YK, Monji A, Mitsui T, Takatsu M

et al (2012) Dipeptidyl peptidase-4 modulates left ventricular

Trang 16

dysfunction in chronic heart failure via angiogenesis-dependent

and -independent actions Circulation 126: 1838–1851

Shiomi T, Tsutsui H, Ikeuchi M, Matsusaka H, Hayashidani S,

Suematsu N et al (2003) Streptozotocin-induced hyperglycemia

exacerbates left ventricular remodeling and failure after

experimental myocardial infarction J Am Coll Cardiol 42: 165–172

Shiraki A, Oyama J, Komoda H, Asaka M, Komatsu A, Sakuma M

et al (2012) The glucagon-like peptide 1 analog liraglutide reduces

TNF-α-induced oxidative stress and inflammation in endothelial

cells Atherosclerosis 221: 375–382

Sokos GG, Nikolaidis LA, Mankad S, Elahi D, Shannon RP (2006)

Glucagon-like peptide-1 infusion improves left ventricular ejection

fraction and functional status in patients with chronic heart failure

J Card Fail 12: 694–699

Sonne DP, Engstrøm T, Treiman M (2008) Protective effects of

GLP-1 analogues exendin-4 and GLP-1 (9-36) amide against

ischemia-reperfusion injury in rat heart Regul Pept 146: 243–249

Stamler J, Vaccaro O, Neaton JD, Wentworth D (1993) Diabetes,

other risk factors, and 12-yr cardiovascular mortality for men

screened in the Multiple Risk Factor Intervention Trial Diabetes

Care 16: 434–444

Stratton I, Cull C, Adler A, Matthews D, Neil H, Holman R (2006)

Additive effects of glycaemia and blood pressure exposure on risk of

complications in type 2 diabetes: a prospective observational study

(UKPDS 75) Diabetologia 49: 1761–1769

Tesauro M, Schinzari F, Adamo A, Rovella V, Martini F, Mores N

et al (2013) Effects of GLP-1 on forearm vasodilator function and

glucose disposal during hyperinsulinemia in the metabolic

syndrome Diabetes Care 36: 683–689

Timmers L, Henriques JP, de Kleijn DP, DeVries JH, Kemperman H,

Steendijk P et al (2009) Exenatide reduces infarct size and

improves cardiac function in a porcine model of ischemia and

reperfusion injury J Am Coll Cardiol 53: 501–510

Toft-Nielsen M, Madsbad S, Holst JJ (1999) Continuous

subcutaneous infusion of glucagon-like peptide 1 lowers plasma

glucose and reduces appetite in type 2 diabetic patients Diabetes

Care 22: 1137–1143

Tremblay A, Lamarche B, Deacon CF, Weisnagel S, Couture P

(2011) Effect of sitagliptin therapy on postprandial lipoprotein

levels in patients with type 2 diabetes Diabetes Obes Metab 13:

366–373

Turner R, Millns H, Neil H, Stratton I, Manley S, Matthews D et al.

(1998) Risk factors for coronary artery disease in non-insulin

dependent diabetes mellitus: United Kingdom Prospective Diabetes

Study (UKPDS: 23) BMJ 316: 823–828

Van Gaal LF, Mertens IL, Christophe E (2006) Mechanisms linking

obesity with cardiovascular disease Nature 444: 875–880

Varanasi A, Chaudhuri A, Dhindsa S, Arora A, Lohano T, Vora MR

et al (2011) Durability of effects of exenatide treatment on

glycemic control, body weight, systolic blood pressure, C-reactive

protein, and triglyceride concentrations Endocr Pract 17: 192–200

Vasan RS, Larson MG, Leip EP, Evans JC, O’Donnell CJ, Kannel WB

et al (2001) Impact of high-normal blood pressure on the risk of

cardiovascular disease N Engl J Med 345: 1291–1297

Verdich C, Toubro S, Buemann B, Lysgård Madsen J, Juul Holst J,Astrup A (2001) The role of postprandial releases of insulin andincretin hormones in meal-induced satiety – effect of obesity andweight reduction Int J Obes Relat Metab Disord 25: 1206–1214.Vergès B, Zeller M, Dentan G, Beer J-C, Laurent Y, Janin-Manificat L

et al (2007) Impact of fasting glycemia on short-term prognosis

after acute myocardial infarction J Clin Endocrinol Metab 92:2136–2140

Vilsbøll T, Zdravkovic M, Le-Thi T, Krarup T, Schmitz O, Courrèges

J-P et al (2007) Liraglutide, a long-acting human glucagon-like

peptide-1 analog, given as monotherapy significantly improvesglycemic control and lowers body weight without risk ofhypoglycemia in patients with type 2 diabetes Diabetes Care 30:1608–1610

Wang D, Luo P, Wang Y, Li W, Wang C, Sun D et al (2013).

Glucagon-like peptide-1 protects against cardiac microvascularinjury in diabetes via a cAMP/PKA/Rho-dependent mechanism.Diabetes 62: 1697–1708

White WB, Cannon CP, Heller SR, Nissen SE, Bergenstal RM, Bakris

GL et al (2013) Alogliptin after acute coronary syndrome in

patients with type 2 diabetes N Engl J Med 369: 1327–1335.Willett WC, Dietz WH, Colditz GA (1999) Guidelines for healthyweight N Engl J Med 341: 427–434

Wright EJ, Farrell KA, Malik N, Kassem M, Lewis AL, Wallrapp C

et al (2012) Encapsulated glucagon-like peptide-1-producing

mesenchymal stem cells have a beneficial effect on failing pighearts Stem Cells Transl Med 1: 759–769

Ye Y, Qian J, Castillo AC, Ling S, Ye H, Perez-Polo JR et al (2013).

Phosphodiesterase-3 inhibition augments the myocardial infarctsize-limiting effects of exenatide in mice with type 2 diabetes Am JPhysiol Heart Circ Physiol 304: H131–H141

Yoshihara M, Akasaka H, Ohnishi H, Miki T, Furukawa T, Yuda S

et al (2013) Glucagon-like peptide-1 secretory function as an

independent determinant of blood pressure: analysis in theTanno-Sobetsu study PLoS ONE 8: e67578

Younce CW, Burmeister MA, Ayala JE (2013) Exendin-4 attenuateshigh glucose-induced cardiomyocyte apoptosis via inhibition ofendoplasmic reticulum stress and activation of SERCA2a Am JPhysiol Cell Physiol 304: C508–C518

Yu M, Moreno C, Hoagland KM, Dahly A, Ditter K, Mistry M et al.

(2003) Antihypertensive effect of glucagon-like peptide 1 in Dahlsalt-sensitive rats J Hypertens 21: 1125–1135

Zhao T, Parikh P, Bhashyam S, Bolukoglu H, Poornima I, Shen Y-T

et al (2006) Direct effects of glucagon-like peptide-1 on myocardial

contractility and glucose uptake in normal and postischemicisolated rat hearts J Pharmacol Exp Ther 317: 1106–1113

Zinman B, Gerich J, Buse JB, Lewin A, Schwartz S, Raskin P et al.

(2009) Efficacy and safety of the human glucagon-like peptide-1analog liraglutide in combination with metformin and

thiazolidinedione in patients with type 2 diabetes (LEAD-4 Met+TZD) Diabetes Care 32: 1224–1230

Trang 17

1Division of Molecular Biology, GW Pharmaceuticals, Salisbury, Wiltshire, UK,2GW

Pharmaceuticals, Porton Down Science Park, Salisbury, Wiltshire, UK,3

Endocannabinoid Research Group, Institute of Biomolecular Chemistry, CNR, Napoli, Italy, and4

School of Medical Sciences, Institute of Medical Sciences, University of Aberdeen, Foresterhill, Aberdeen, UK

Correspondence

Dr John M McPartland, 53Washington Street Ext.,Middlebury, VT 05753, USA

Based upon evidence that the therapeutic properties of Cannabis preparations are not solely dependent upon the presence of

mechanistic studies of CBD and THCV, and synthesize data from these studies in a meta-analysis Synthesized data regardingmechanisms are then used to interpret results from recent pre-clinical animal studies and clinical trials The evidence indicatesthat CBD and THCV are not rimonabant-like in their action and thus appear very unlikely to produce unwanted CNS effects

rimonabant These cannabinoids illustrate how in vitro mechanistic studies do not always predict in vivo pharmacology and underlie the necessity of testing compounds in vivo before drawing any conclusion on their functional activity at a given

target

Abbreviations

2-AG, sn-2 arachidonoyl glycerol; AEA, anandamide; CBD, cannabidiol; CV, coefficient of variation; DAGL,

diacylglycerol lipase; FAAH, fatty acid amide hydrolase; FsAC, forskolin-stimulated adenylate cyclase; MAFP,

methylarachidonoyl fluorophosphonate; MAGL, monoacylglycerol lipase; PMSF, phenylmethyl sulfonyl fluoride; THCV,

Trang 18

Isolating and identifying the ‘primary active ingredient’ in

Cannabis (the plant) and cannabis (the plant product)

stymied chemists for over 150 years Finally, Gaoni

Δ9-tetrahydrocannabinol (THC) THC and biosynthetically

related and structurally similar plant cannabinoids are now

called phytocannabinoids to distinguish them from

structur-ally dissimilar but pharmacologicstructur-ally analogous

(synthocannabinoids)

THC exerts most of its physiological actions via the

endo-cannabinoid system The endoendo-cannabinoid system consists

of (i) GPCRs for THC, known as cannabinoid receptors; (ii)

endogenous cannabinoid receptor ligands; and (iii) ligand

metabolic enzymes The salient homeostatic roles of the

endocannabinoid system have been roughly portrayed as

‘relax, eat, sleep, forget, and protect’ (Di Marzo et al., 1998).

When malfunctioning, the endocannabinoid system can

contribute to pathological states (Russo, 2004; Di Marzo,

2008)

All vertebrate animals express at least two cannabinoid

receptors The CB1 receptor principally functions in the

nervous system but is expressed in many cells throughout the

body CB2 receptors are primarily associated with cells

gov-erning immune function, such as splenocytes, macrophages,

monocytes, microglia, and B- and T-cells Recent evidence

demonstrates the presence of CB2 receptors in other cells,often up-regulated under pathological conditions (reviewed

in Pertwee et al., 2010).

N-arachidonylethanolamine (anandamide, AEA) and2-arachidonoylglycerol (2-AG) One of AEA’s key biosyn-

thetic enzymes is N-acyl-phosphatidylethanolamine

phos-pholipase D The chief biosynthetic enzymes of 2-AG are twoisoforms of diacylglycerol lipase: DAGLα and DAGLβ Theprimary catabolic enzymes of AEA and 2-AG are fatty acidamide hydrolase (FAAH) and monoacylglycerol lipase(MAGL) respectively COX-2 can also catabolize AEA and

2-AG (Kozak et al., 2002).

Synthetic THC (dronabinol) became clinically available inthe 1980s for indications including anorexia and weight loss

in people with AIDS, and for nausea and vomiting associatedwith cancer chemotherapy Off-label uses include migraine,multiple sclerosis, sleep disorders and chronic neuropathicpain However, the therapeutic window of THC is narrowed

by side effects In clinical trials, dronabinol precipitated phoria, depersonalization, anxiety, panic reactions and para-

dys-noia (Cocchetto et al., 1981).

Psychological side effects occur more frequently withTHC than with whole cannabis (Grinspoon and Bakalar,1997) Only six years after Raphael Mechoulam successfullyisolated THC, one of the authors of this article determined

that THC did not act alone in cannabis (Gill et al., 1970).

Other constituents in cannabis work in a paradoxical capacity

Tables of Links

TARGETS

lipase5-HT1Areceptors PLA2

Adenosine A2Areceptors Ion channelsc

DAGLα, diacylglycerol lipase α Glycineα3 receptors

DAGLβ, diacylglycerol lipase β Nuclear hormone

FAAH, fatty acid amide hydrolase PPARγ (NR1C3)

iNOS, inducible NOS

LIGANDS

2-AG, 2-arachidonoylglycerol5-HT

AEA, anandamideAM251

CBD, cannabidiolCP55940LTB4NORimonabant, SR141716ATHC,Δ9-tetrahydrocannabinolTHCV,Δ9-tetrahydrocannabivarinWIN55212-2

These Tables list key protein targets and ligands in this article which are hyperlinked to corresponding entries in http://

www.guidetopharmacology.org, the common portal for data from the IUPHAR/BPS Guide to PHARMACOLOGY (Pawson et al., 2014) and are

permanently archived in the Concise Guide to PHARMACOLOGY 2013/14 (a,b,c,d,e,f Alexander et al., 2013a,b,c,d,e,f).

Trang 19

of mitigating the side effects of THC, but improving the

therapeutic activity of THC

Cannabidiol (CBD) and

Δ9-tetrahydrocannabivarin (THCV)

At last count, 108 phytocannabinoids have been

character-ized in various chemovars of the plant (Hanuš, 2008) The

other phytocannabinoids of greatest clinical interest are CBD

and THCV THC and CBD are ‘sister’ molecules,

biosynthe-sized by nearly identical enzymes in Cannabis – expressions of

two alleles at a single gene locus (de Meijer et al., 2003) THC

and CBD are C21 terpenophenols with pentyl alkyl tails,

whereas THCV is a C19propyl-tailed analogue of THC

Can-nabis biosynthesizes these compounds as carboxylic acids,

for example, THC-carboxylic acid (2-COOH-THC) When

heated, dried or exposed to light, the parent compounds are

decarboxylated

Fundamentally, THC mimics AEA and 2-AG by acting as a

partial agonist at CB1and CB2receptors (Mechoulam et al.,

1998) But rather than simply substituting for AEA and 2-AG,

cannabis and its many constituents work, in part, by

‘kick-starting’ the endocannabinoid system (McPartland and Guy,

2004) CBD, in particular, gained attention early in this

regard Several landmark studies published in the previous

century have shown interactions between CBD and THC (see

Box 1)

Meta-analysis

Many narrative reviews have been written about THC, CBDand THCV, and cannabis as a ‘synergistic shotgun’(McPartland and Pruitt, 1999; McPartland and Russo, 2001;

Mechoulam et al., 2007; Zuardi, 2008; Izzo et al., 2009; Russo,

2011) CBD by itself has many therapeutic properties: lytic, antidepressant, antipsychotic, anticonvulsant, anti-nausea, antioxidant, anti-inflammatory, anti-arthritic andantineoplastic

anxio-The ability of CBD to antagonize THC has been the focus

of many narrative reviews, as well as the studies listed inBox 1 This has led to the assumption that CBD exerts a directpharmacodynamic blockade of THC The pharmacologicalcommunity tends to view CBD and THCV as negative modu-lators of CB1 receptor agonists This view may be due to asuperficial interpretation of the available pharmacologicaldata Hence, CBD and THCV would appear to mirror themechanism of first-generation CB1 receptor inverseagonists known as cannABinoid ANTagonists (‘abants’), such

as rimonabant, taranabant, otenabant and ibipinabant.Rimonabant was developed as an anti-obesity agent and mar-keted as an adjuvant to diet and exercise for weight loss inobese individuals It was subsequently withdrawn from themarket due to adverse psychiatric side effects (Bermudez-Silva

et al., 2010).

Box 1 Landmark 20th century studies regarding the effects of CBD upon THC.a

Animal studies

CBD combined with isomeric tetrahydrocannabinols caused ‘synergistic hypnotic activity in the mouse’ – Loewe and Modell, 1941

CBD inhibited THC effects on mouse catatonia, rat ambulation and rat aggression, but potentiated THC effects on mouse analgesia and ratrope climbing – Karniol and Carlini, 1973

CBD decreased THC suppression of behaviour in rats and pigeons – Davis and Borgen, 1974

CBD potentiated THC-induced changes in hepatic enzymes – Poddar et al., 1974.

CBD increased THC potentiation of hexobarbitone in rats – Fernandes et al., 1974.

CBD increased THC reduction of intestinal motility in mice – Anderson et al., 1974.

CBD reduced THC hypothermia and bradycardia – Borgen and Davis, 1974

CBD blocked THC inhibition of pig brain monamine oxidase – Schurr and Livne, 1976

CBD antagonized THC antinociceptive effects in mice – Welburn et al., 1976.

CBD prevented tonic and clonic convulsions induced by THC – Consroe et al., 1977.

CBD antagonized THC suppression of operant behaviour in monkeys – Brady and Balster, 1980

CBD delayed THC discriminative effects – Zuardi et al., 1981.

CBD prolonged THC cue effects in rats – Hiltunen and Järbe, 1986

CBD antagonized THC catalepsy in mice – Formukong et al., 1988a.

CBD increased THC analgesic activity and anti-erythema – Formukong et al., 1988b.

CBD prolonged and reduced the hydroxylation of THC – Bornheim et al., 1995, 1998.

Human clinical trials

CBD decreased anxiety caused by THC – Karniol et al., 1974.

CBD slightly increased time to onset, intensity and duration of THC intoxication – Hollister and Gillespie, 1975

CBD attenuated THC euphoria – Dalton et al., 1976.

CBD reduced anxiety provoked by THC – Zuardi et al., 1982.

CBD improved sleep and decreased epilepsy – Cunha et al., 1980; Carlini and Cunha, 1981.

CBD decreased cortisol secretion and had sedative effects – Zuardi et al., 1993.

CBD provided antipsychotic benefits – Zuardi et al., 1995.

aFull citations appear in previous reviews (McPartland and Pruitt, 1999; McPartland and Russo, 2001; Russo and Guy, 2006)

Trang 20

We hypothesize that CBD and THCV may, under certain

conditions, ‘antagonize’ the effects of THC via mechanisms

other than direct CB1receptor blockade The purpose of this

article is to review mechanistic studies (in vitro and ex vivo) of

CBD and THCV Rather than a narrative review, we will

conduct a meta-analysis The results of this synthesis of

mechanistic studies will be applied to an emerging

discus-sion: do CBD and THCV act as natural ‘abants’?

Methods

Meta-analysis uses an objective, transparent approach for

research synthesis, with the aim of minimizing bias A valid

meta-analysis combines data from independent studies,

identifies sources of heterogeneity among the studies and

manages heterogeneity by placing defined limits upon data

selection (Glass et al., 1981) This methodology usually

focuses upon human clinical trials, but it can be applied to

pre-clinical studies We previously conducted a meta-analysis

on CB1 receptor ligand binding affinity (McPartland et al.,

2007) We follow the guidelines proposed by PRISMA, the

Preferred Reporting Items for Systematic Reviews and

Meta-Analyses (Liberati et al., 2009) See Supporting Information

Appendix S1

Search strategy and study selection

We briefly describe the analysis here For details regarding

inclusion criteria, heterogeneity tests, subgroup analysis,

quality assessment and publication bias, see Supporting

Information Appendix S1

PubMed (www.ncbi.nlm.nih.gov/pubmed/) was searched

from 1988 (beginning with Devane et al., 1988) through

December 2013, using the following Boolean search string:

(cannabidiol OR tetrahydrocannabivarin) AND (animal OR

affinity OR efficacy) NOT (behavioral OR behavioural)

Refer-ences identified by the search strategy were scanned for

inclu-sion and excluinclu-sion criteria by three independent reviewers

who resolved disagreements by consensus

Inclusion criteria included studies of CBD or THCV, their

carboxylic acids (CBD-acid, THCV-acid), as well as CBD- or

THCV-enriched plant extracts (‘botanical drug substances,’

CBD-BDS, THCV-BDS) Included studies reported in vitro or ex

vivo mechanistic data (receptor affinity and efficacy assays),

detailed in Supporting Information Appendix S1

The rather broad search strategy retrieved many articles

that were subsequently excluded as irrelevant Excluded

topics included (i) review articles or publications with

dupli-cated data; (ii) animal studies or in vivo studies without

mechanisms or an identified molecular target; (iii) studies of

synthetic analogues, or metabolites of CBD or THCV; (iv)

human clinical trials lacking mechanistic analysis; urinary

metabolites of CBD and THCV and their use in drug testing;

characterizations of cannabinoid drug delivery systems; and

(v) other irrelevant topics (see Supporting Information

Appendix S1 for elaboration)

Articles meeting inclusion and exclusion criteria were

screened for supporting citations, and antecedent sources

were retrieved The search also included unpublished data

communicated at research conferences, upon approval by the

authors of the data Lastly, we contacted world experts andasked them to contribute unpublished data (see Acknowl-edgements section)

Data extraction and synthesis

Extracted data included ligand (CBD or THCV), assay type,animal species, reported means, sample variance, sample sizeand methodological factors Methodological factors (covari-ates) were extracted for use in subgroup analyses to testwhether they exerted heterogeneous effects upon pooledmeans Methodological factors were pre-specified, chosen in

advance by a priori hypotheses based upon recognized odological diversity among studies, and not undertaken after the results of the studies had been compiled (post hoc

meth-analyses)

Data were synthesized qualitatively (e.g categorical data)

or quantitatively [e.g the continuous variables for affinity (K i)

and efficacy (EMAX)] A quantitatively synthesized result isreported as a pooled mean± SEM Optimal quantitative syn-thesis would employ a weighted pooled mean, which adjustseach study’s mean divided by its SEM, because larger studieswith less variance should carry more ‘weight’ in a meta-analysis Unfortunately, many studies omitted variance data

or sample size

To determine whether pooling was statistically ate, the coefficient of variation (CV) was determined foreach pooled mean The CV measures data dispersion of aprobability distribution, defined simply as the ratio of the SD

appropri-to the mean (Reed et al., 2002) We applied the Cochrane

‘skew test’ to the CV (Higgins and Green, 2005), where CV≥

1 (i.e SD ≥ mean) identifies a skewed mean with excessiveheterogeneity Skewed mean was submitted to Grubb’s test(www.graphpad.com/quickcalcs/) Data identified as signifi-

cant outliers (P< 0.05) were reported in Supporting tion Appendices S2 and S3 and withdrawn from synthesis

Informa-The CV-skew test could not be used for sample sizes of n≤ 3

In those cases, we used simple pooled means

Results

The search algorithm identified 431 potentially relevant cles Many of these publications were review articles or con-cerned topics irrelevant to this review In addition to 174articles that met the predefined selection criteria for rel-evance, we included 28 studies obtained from citation track-ing or unpublished studies See Figure 1 for a flowchart.The quality of statistical reporting has steadily improvedbetween 1984 and 2013 For example, early studies that meas-

arti-ured the K iof CBD reported variance as SD, and sometimesomitted variance data or sample sizes (Supporting Informa-tion Appendix S2) Later studies reported variance as SEM

However, K ivalues are not symmetric around a mean, and thebest way to report non-parametric variance is the use of 95%confidence limits/intervals rather than SEM

CBD has many molecular targets; we grouped them inthree categories The first category addresses the effects ofCBD and THCV at CB1receptors – directly and indirectly Thenext category includes what some researchers consider

an ‘expanded’ endocannabinoid system – other GPCRs (CB2,

Trang 21

GPR55, GPR18), and transient receptor potential ion

chan-nels (e.g TRPV1, TRPV2, TRPA1, TRPM8) The third category

includes receptors and ligand enzymes beyond the expanded

system, as well as the arachidonic acid (AA) cascade, nitric

oxide signalling, cytokines, redox signalling and mechanisms

involved in apoptosis

CBD at CB1 receptors: direct and

indirect interactions

The pooled mean affinity of CBD at CB1receptors is K i= 3245

± 803 nM The pooled mean was calculated from 1 human, 3

mice and 11 rat studies (Supporting Information

Appen-dix S2) Species differences were not statistically different,

including the human study (K i = 1510 ± 100 nM) Several

studies omitted quality measures such as statistical data

(vari-ance and/or sample size) Subgroup analysis of the five

meth-odological factors produced surprising results Only one

factor – the use of crude brain homogenates – proved to be

statistically relevant (Supporting Information Appendix S2)

None of the other factors gave rise to data heterogeneity –

species differences, class of tritiated ligand (agonist vs

antagonist) or even the use of non-specific probes (e.g

[3H]TMA-THC) One methodological factor could not be

assessed – no studies used PMSF

Eight studies tested CBD efficacy at CB1receptors, assayed

with forskolin-stimulated adenylate cyclase (FsAC) or

[35S]GTPγS (Supporting Information Appendix S2) Six of

these studies reported no measurable response or inconsistent

dose–response curves hovering near zero One study reported

slight agonism, and one study reported slightly inverse

agonism, both at high concentrations (≥10 μM)

Surprisingly, in some mechanistic studies, the effects of

CBD could be reversed by CB1 receptor inverse agonists, or

were absent in CB1receptor knockout mice (n= 10 studies;

Supporting Information Appendix S2) This suggests that CBD

may exert ‘indirect agonism’ at CB1 receptors – either

aug-menting CB1 constitutional activity or augaug-menting

endocan-nabinoid tone Regarding the first mechanism, Howlett et al.

(1989) presented thermodynamic data that suggest that CBD

may alter CB1receptor activity by increasing membrane

fluid-ity Sagredo et al (2011) showed that Sativex®(a mix of THCand CBD; GW Pharmaceuticals, Salisbury, UK) can up-regulate

CB1receptor gene expression in a rat model of Huntington’sdisease The second mechanism – augmenting endocannabi-noid tone – is supported by studies showing that CBD or

CBD-BDS inhibits AEA hydrolysis by FAAH (n = 5 studies;Supporting Information Appendix S2), with a pooled mean

IC50= 19.8 ± 4.77 μM Four rodent studies show that CBDinhibits the putative AEA transporter, with a pooled mean IC50

= 10.2 ± 3.03 μM Two studies reported CBD increasing 2-AGlevels, 33 or 260% (Supporting Information Appendix S2).CBD may affect the pharmacokinetics of THC when the

two are co-administered (n= 17 studies; Supporting tion Appendix S2) One of these pharmacokinetic studiespredates the isolation of pure THC – Loewe and Modell(1941) stated that CBD ‘synergized’ hypnotic action in miceinduced by isomeric tetrahydrocannabinols CBD may impairTHC hydrolysis by CYP450 enzymes The results of CYPstudies vary due to species differences, timing (CBD pre-administration vs co-administration) and specific CYP isoen-zymes Recent human studies show no pharmacokineticinteraction between THC and CBD at clinically relevantdosing (Supporting Information Appendix S2)

Informa-The effect of CBD on CYPs is important because theseenzymes metabolize THC into 11-OH-THC This metabolitemay be up to four times more psychoactive than THC,according to a rat discriminative study (Browne andWeissman, 1981) The affinity and efficacy of 11-OH-THC at

CB1receptors has not been measured, although the affinity of11-OH-Δ8-THC was K i= 25.8 nM, displacing [3H]HU-243 fromrCB1COS cells (Rhee et al., 1997) In the same assay,Δ9-THC

exhibited K i = 80.3 nM (Rhee et al., 1997) or K i = 39.5 nM

(Bayewitch et al., 1996) The significance of CBD modulating

the metabolism of THC into 11-OH-THC is an importantvariable that remains to be explored

CBD may antagonize cannabinoid-induced effects Six in

vitro studies demonstrate that CBD can antagonize

CP55,940-or WIN55212-2-induced efficacy (SuppCP55,940-orting InfCP55,940-ormation

Appendix S2), with a pooled mean KB= 88.5 ± 18.46 nM This

unexpected KBis 37-fold more potent than the K iof CBD inbinding assays This suggests an indirect mechanism, that is,

mediated by (an)other target(s) The KBof CBD is 147-fold

higher (less potent) than the KB of rimonabant, when this

inverse agonist was run in parallel (n= 3 studies; SupportingInformation Appendix S2) Note that this antagonism can bevisualized by juxtaposing two log concentration–responsecurves; for example, the curve of CP55,940 for stimulation of[35S]GTPγS binding to CB1receptors, compared to the curve ofCP55,940 for such stimulation in the presence of CBD Acompetitive antagonist would produce a parallel rightward

shift in the curve of CP55,940 However, Petitet et al (1998)

found CBD to produce a parallel shift in the curve ofCP55,940 that was downward rather than rightward in itsdirection, an effect that a competitive antagonist is notexpected to produce

CBD at targets in the ‘expanded endocannabinoid system’

The ability of CBD to antagonize a cannabinoid agonist in anefficacy assay may be confounded by the impact of CBD on

Figure 1

Flow diagram of article selection for meta-analysis

Trang 22

other receptors or enzymes present in the assay In Table 1, we

summarize studies regarding CBD affinity and efficacy at

other metabotropic receptors and ion channels in the

‘expanded endocannabinoid system.’

CBD shows low affinity at CB2 receptors (Table 1) Its

efficacy at CB2 receptors suggests weak inverse agonism at

concentrations that may not be pharmacologically relevant

However, CBD antagonizes CP55,940 signalling at CB2

recep-tors with a KBpotency not commensurate with its K i This

suggests again an indirect mechanism of action At GPR18,

two studies suggest that CBD acts as a partial agonist and

antagonizes THC (Supporting Information Appendix S2) The

direct affinity and efficacy of CBD at GPR55 has not been

measured, but it can antagonize GPR55 agonists (Supporting

Information Appendix S2)

Table 1 highlights CBD signalling at transient receptor

potential (TRP) channels, which have been characterized as

‘ionotropic cannabinoid receptors’ (Di Marzo et al., 2002).

We find a species difference at TRPV1 channels and the

(Table 1), whereas a single study of rat TRPV1 channels

reports an EMAXof 21% (Qin et al., 2008) At TRPA1 channels,

the pooled mean EMAX of CBD (Table 1) is considerably less

than that of CBD-BDS (163.6± 11.9%; De Petrocellis et al.,

2011) This suggests that terpenoids and other plant

sub-stances in the extract may enhance CBD activity at TRPA1

channels, either pharmacokinetically or

pharmacodynami-cally The same study showed that CBD-BDS also showed

slightly greater efficacy than pure CBD at TRPV1 channels

(Supporting Information Appendix S2) CBD acts as an

antagonist at TRPM8, unlike its agonist activity at other TRP

channels (Table 1)

CBD at other molecular targets

CBD is a promiscuous compound with activity at multipletargets Promiscuity is governed by ligand structure, and can-nabinoids exhibit the characteristics of promiscuous ligands:molecular mass >400 g·mol−1, and partition coefficient(CLogP) scores between 2 and 7 (Hopkins, 2008)

CBD inhibits adenosine uptake (pooled IC50 = 122 nM

minus one outlier, n = 3 studies; Supporting InformationAppendix S2) and this mechanism is likely to exert indirectagonism at adenosine receptors Consistent with this, thebeneficial effects of CBD in animal models of inflammationare blocked by adenosine A2A receptor antagonists (n = 8studies) CBD may also regulate 5-HT levels, although sixstudies report disparate results CBD has slight affinity for the5-HT1Areceptor (K i∼ 16 μM; Supporting Information Appen-dix S2), although its efficacy at 5-HT1Areceptors is inconsist-

ent Several beneficial effects of CBD in vivo are blocked

by 5-HT1A receptor antagonists (Supporting InformationAppendix S2)

CBD exerts a positive allosteric modulation ofα3 glycinereceptors (pooled EC50= 11.0 μM, n = 3 studies; Supporting

Information Appendix S2) NMR analysis revealed a directinteraction between CBD and S296 in the third transmem-brane domain of α3 glycine receptors The cannabinoid-induced analgesic effect was absent in mice lacking theα3

glycine receptors (Xiong et al., 2011) CBD can go nuclear,

as it affects PPARγ receptors (IC50 = 5 μM; SupportingInformation Appendix S2), and its beneficial effects areblocked by PPARγ antagonists (n = 5 studies) A dozen studiesindicate that CBD allosterically modulates other receptors:

α1-adrenoceptors, dopamine D2, GABAA, μ- and δ-opioid

CB2receptor A: versus [3H]CP55,940 binding; human CB2transfected cell cultures, or rat

RBL-2H3 leukemia cells, centrifuged membranes

K i = 3612 ± 1382 nM, n = 6

CB2receptor E: [35S]GTPγS binding; human CB2-CHO cells EMAX= −15% below basal at 10 μM

EC50= 503 ± 2080 nM; n = 1

CB2receptor E: antagonism of CP55,940-induced [35S]GTPγS binding; human CB2-CHO cells KB= 65 ± 54.1 nM, n = 1

GPR55 E: antagonism of agonist-induced signalling; human cell cultures or CB2-CHO cells IC50= 433 ± 42.6 nM, n = 3

TRPV1 channels A: versus [3

H]-resiniferatoxin binding; human TRPV1-HEK293 cell membranes K i = 3600 ± 200 (SD) nM, n = 1

TRPV1 channels E: [Ca2+]ielevation in human TRPV1-HEK293 cells EMAX53.4± 5.03%; n = 4

EC50= 1900 ± 802 nMTRPA1 channels E: [Ca2 +]ielevation in rat TRPA1-HEK293 cell membranes EMAX98.6± 10.39%

aA, affinity; E, efficacy Other abbreviations as defined in the manuscript

bNumber of studies that met the CV-Cochrane ‘skew test’ (see Supporting Information Appendix S2)

Trang 23

receptors – some positively, some negatively, none with great

efficacy (Supporting Information Appendix S2) CBD

modu-lates intracellular calcium levels, via T-type and L-type

voltage-regulated Ca2 +channels and mitochondrial Na+/Ca2 +

exchange (n= 7 studies)

The effects on the AA cascade are complex Three studies

indicate that CBD mobilizes AA by stimulating PLA2activity

The direction that AA goes from there is uncertain CBD

inhibits the metabolism of AA to LTB4 by 5-lipoxygenase –

pooled IC50= 3.1 ± 0.75 μM, n = 4 studies, although a fifth

study reported no effect up to 80μM (Supporting

Informa-tion Appendix S2) Contradictory studies report CBD

block-ing the metabolism of AA to PGE1 or TxB2 (via COX-1) or

PGE2(via COX-2) Early studies did not identify which COX

isoenzyme they tested Recent studies indicate that CBD

attenuates serum PGE2in animal models of chronic pain, but

this may or may not correlate with COX-2 protein expression

(Supporting Information Appendix S2)

CBD clearly dampens NO production in animal models of

acute and chronic inflammation – as measured by a reduction

in nitrite levels or inducible NOS (iNOS) protein expression (n

= 15 studies) A dozen studies show that CBD inhibits the

expression of inflammatory cytokines and transcription

factors (IL-1β, IL-2, IL-6, IL-8, TNF-α, IFN-γ, CCL3, CCL4,

NF-κB)

CBD is a potent antioxidant; it reduces reactive oxygen

species (ROS) induced by a variety of toxins and tissue insults

(Supporting Information Appendix S2) However, one study

suggests the opposite – that CBD hydroxyquinone, formed

during hepatic microsomal metabolism of CBD, is capable of

generating ROS and inducing cytotoxicity Indeed, one

mechanism by which CBD induces tumour cell apoptosis

appears to be ROS generation (Supporting Information

Appendix S2) In general, it appears that CBD can induce ROS

in cancer cells and reduce ROS in healthy cells stimulated by

agents that induce ROS formation In fact, even in cancer

cells, CBD inhibits ROS formation induced by H2O2(Ligresti

et al., 2006).

THCV at CB1 and CB2

Affinity studies show that THCV binds to CB1receptors with

significant potency There may be species differences – at

human CB1receptors transfected into CHO cells, mean K i=

5.47± 4.02 nM (n = 2 studies); at mouse brain membranes,

mean K i = 61.0 ± 14.40 nM (n = 2); and at rat brain

mem-branes (n = 1), mean K i= 286 ± 43 nM The rat study used

[3H]SR141716A, whereas others used [3H]CP55,940

(Support-ing Information Appendix S3)

Four studies tested the efficacy of THCV at CB1receptors

THCV did not inhibit or stimulate [35S]GTPγS binding to

mouse whole brain membranes (n= 3 studies) or to rat

mem-branes (cortical, cerebellar or piriform cortical memmem-branes) at

concentrations up to 10μM This suggests that THCV targets

the CB1 receptor as a neutral antagonist rather than as an

antagonist/inverse agonist The single study that tested FsAC

in human CB1 receptors in CHO cells produced signs of

inverse agonism at concentrations of 10, 100 and 1000 nM

(Supporting Information Appendix S3)

In the presence of other cannabinoids, THCV binds to

CB1, in vitro, in a manner that gives rise to competitive

antagonism rather than to agonism More specifically, THCV

produces significant parallel rightward shifts in the logconcentration–response curves of established CB1 receptoragonists such as CP55,940 or WIN55212-2, in [35S]GTPγSbinding to mouse whole brain membranes, and in the inhi-bition of electrically evoked contractions of mouse isolatedvasa deferentia Pooling five studies (Supporting Information

Appendix S3) results in a KB= 64.2 ± 14.14 nM Thus, the KB

of THCV is in the same range of concentrations as its K i.The five studies hint at ‘probe dependence’ That is, THCVhas greater potency when antagonizing WIN55212-2 thanwhen antagonizing CP55,940, although the difference fallsshort of statistical significance (Supporting InformationAppendix S3) Two studies of THCV as an antagonist in thevas deferens assay also hint at probe dependence – thepotency of THCV is not the same for all CB1receptor agonists

In rank order: AEA (KB= 1.2 nM), methAEA (KB= 2.6 nM),

WIN55212-2 (KB= 3.15 nM), CP55,940 (KB= 10.3 nM), THC

(KB= 96.7 nM) (Supporting Information Appendix S3) THCValso reverses WIN55212-2-induced decreases of miniatureinhibitory postsynaptic current frequency at mouse cerebellarinterneuron-Purkinje cell synapses, albeit with much lesspotency than the CB1receptor inverse agonist AM251, whichwas tested in parallel (Supporting Information Appendix S3)

At human CB2 receptors transfected into CHO cells,

THCV has significant affinity, with pooled mean Ki= 124.7 ±

64.55 nM (n = 3 studies; Supporting Information dix S3) THCV acts as a partial agonist at these receptors asmeasured by [35S]GTPγS binding or FsAC assays, pooled EMAX=56.7 from basal at 1–10μM, EC50 = 74.2 ± 34.4 nM (n = 3

Appen-studies; Supporting Information Appendix S3)

THCV may exert ‘indirect agonism’ at CB1and CB2tors by augmenting endocannabinoid tone It does this byinhibiting the putative AEA transporter, inhibiting FAAHactivity and inhibiting MAGL activity, albeit at 25–100μM (n

recep-= 3 studies; Supporting Information Appendix S3) Whether

or not THCV exerts ‘indirect agonism’ to an extent that canovercome its surmountable CB1receptor antagonism requiresfurther experiments

THCV at other targets

Unlike CBD, much less evidence exists for non-cannabinoidreceptor-mediated effects of THCV, and this evidence has to

do mostly with the capability of THCV to interact with

‘thermo-TRP’ channels One study demonstrates that THCVacts as an agonist at rat TRPA1, human TRPV1 and ratTRPV2-4 channels and a potent antagonist at rat TRPM8channels (Supporting Information Appendix S3) Dataregarding its effects at GPR55 are controversial, and thepotentiation of 5-HT1A receptors was observed only atthe concentration of 100 nM (Supporting InformationAppendix S3)

Discussion

Our previous meta-analysis of receptor affinity of several

syn-thetic and natural cannabinoid ligands (McPartland et al.,

2007) involved more studies than this current analysis ofCBD and THCV Subgroup analysis suggests that methodo-logical nuances employed in the larger group of studies (such

as PMSF usage) were absent in studies of CBD and THCV

Trang 24

The low affinity of CBD at CB1and CB2receptors

damp-ened the signal-to-noise ratio to such an extent that some

nuances were rendered unnecessary – subgroup analysis

showed no differences arising from methodological factors

that proved important in our previous meta-analysis, such as

species differences and the quality of tritiated ligand THCV,

on the contrary, with its moderate to high potency in

dis-placement assays for CB1and CB2receptors, hints at species

differences in its affinity at CB1receptors, as well as ‘probe

dependence’ in its ability to antagonize other cannabinoids

Pre-clinical animal studies demonstrated that CBD

expands the therapeutic window of THC CBD may

accom-plish this by enhancing the efficacy of THC as well as by

mitigating the ‘central’ side effects of THC These effects have

been known for some time (Box 1) In particular, our

discus-sion below indicates that CBD enhances the efficacy of THC

in preclinical models of multiple sclerosis, muscle spasticity,

epilepsy, chronic pain and inflammation, anorexia and

nausea, diabetes and metabolic syndrome CBD mitigates the

side effects of THC in animal models of psychosis, anxiety

and depression-anhedonia

CBD at CB1 receptors: direct and indirect

interactions

Let us return to our original question: does CBD act as a

natural ‘abant’? Data clearly show that CBD does not act

directly at CB1receptors The affinity of CBD at CB1receptors

(K i= 3245 nM) is at least three orders of magnitude less than

that of rimonabant (K d= 1.0 nM in rat, 2.9 nM in human;

McPartland et al., 2007) Several efficacy studies made direct

comparisons of [35S]GTPγS binding: CBD showed no

measur-able activity, whereas rimonabant elicited strong inverse

agonism with a mean IMAX= −35.5% (Supporting Information

Appendix S2)

The inactivity of CBD in vitro is confirmed by in vivo

studies CBD does not elicit the classic CB1-mediated tetrad of

hypolocomotion, analgesia, catalepsy and hypothermia

(Long et al., 2010) In drug discrimination studies, CBD failed

to generalize with THC (Järbe et al., 1977; Zuardi et al., 1981)

and did not alter the discriminative stimulus effects of THC

(Vann et al., 2008) Its lack of cannabimimetic effects is well

known in humans (Hollister, 1973)

CBD exerts CB1receptor agonist-like activity in some in

vitro functional assays at high concentrations (>10 μM),

which can be reversed by CB1receptor inverse agonists, and is

absent in CB1 receptor knockouts This probably occurs by

CBD augmenting endocannabinoid tone Pooled rodent

studies show moderate inhibition of FAAH and the putative

AEA transporter CBD may also augment endocannabinoid

tone by activating PLA2, thus mobilizing AA – the feedstock

for AEA and 2-AG synthesis

On the contrary, CBD inhibits adenosine uptake, thereby

acting as an indirect agonist at A2Areceptors Agonism of these

receptors in post-synaptic cells prevents glutamate mGlu5

receptor-mediated release of AEA and 2-AG through A2A/

mGlu5heteromers (Lerner et al., 2010) These opposing effects

– CBD augmenting endocannabinoid tone and augmenting

adenosine tone – often strike a balance in favour of the

former: Robust rodent studies indicate that CBD augments

endocannabinoid tone (e.g Campos et al., 2013) One clinical

study showed that AEA levels increased in schizophrenic

patients given CBD 800 mg·day−1(Leweke et al., 2012) Future

in vitro studies of CBD affinity and efficacy in the presence or

absence of PMSF or MAFP would be instructive (these areFAAH inhibitors that prevent the synthesis of AEA) Knockingdown tonic adenosine A2Areceptor signalling may also shed

light on this complex situation (Savinainen et al., 2003) Our second paradoxical finding is the in vitro capacity of

CBD to ‘functionally antagonize’ cannabinoid-induced ity at CB1 receptors However, the KB of CBD (88.5 ±18.46 nM) is far higher (implying less potency) than that of

activ-rimonabant (mean KBof 0.6± 0.41 nM when tested in parallel

in the same studies; Supporting Information Appendix S2)

Indeed, CBD in vivo mostly behaved in a different way from

that of rimonabant For example, CBD produced no effect onfood intake, energy expenditure or insulin sensitivity in obese

mice (Cawthorne et al., 2008) Its anxiolytic, antidepressant

and anti-nausea effects are all opposite to those reported forrimonabant (Pertwee, 2008) (Box 2)

Non-CB1 receptor mechanisms of CBD antagonism of THC

Earlier we proposed that the functional antagonism of THC

by CBD may be mediated by a non-CB1receptor mechanism

of action Pharmacodynamic antagonism arises when onedrug diminishes the effect of another drug by targeting dif-ferent receptors or enzymes For example, dry mouth caused

by a sympathomimetic drug is antagonized by a cholinergicdrug

We propose several non-CB1 receptor mechanisms ofaction:

1 CBD augments AEA levels Both AEA and CBD have ity for TRPV1 channels and signal as agonists (Table 1)

affin-Pre-synaptic TRPV1 channel activation enhances glutamate

release in the spinal cord and brain This may counteract

or antagonize the inhibitory action of pre-synaptic CB1

receptors co-localizing on glutamatergic neurons (Camposand Guimaraes, 2009; Di Marzo, 2010)

2 CBD inhibits adenosine uptake and therefore acts as anindirect agonist at adenosine receptors Functionally CBDdoes the opposite of caffeine, an adenosine receptor

antagonist (El Yacoubi et al., 2000) There are four

adeno-sine receptor subtypes; cannabinoid research has focused

on A2Areceptors (Table 1) Pre-synaptic A2Areceptors formheteromers with CB1receptors on glutamatergic neurons,and A2Areceptor agonism inhibits CB1receptor-mediated

effects in rat striatum (Martire et al., 2011) Post-synaptic

A2Areceptor signalling is a different story, as we mentionedearlier On the contrary, some effects of CBD are reversed

by the A1 receptor-selective antagonist DPCPX (Castillo

et al., 2010; Maione et al., 2011) Possible indirect agonism

of A1receptors would place CBD in the company of zodiazepines, which target A1, as well as GABAA, receptorsand, like benzodiazepines, might also strengthen, and notonly oppose, CBD indirect activation of CB1receptors in a

ben-tissue-specific manner (see Maione et al., 2011 for an

Trang 25

catalepsy via 5-HT1A receptors (Gomes et al., 2013) It is

tempting to attribute this again to CBD indirect agonism

via AEA – Palazzo et al (2006) demonstrated that sciatic

nerve chronic constriction injury (CCI) elevates AEA in

the dorsal raphe, resulting in 5-HT-mediated hyperactivity

The study also showed that CCI increased extracellular

5-HT levels, a mechanism likely to be shared by CBD

administration, which suppresses enzymatic depletion of

tryptophan, the precursor of 5-HT (Supporting

Informa-tion Appendix S2)

Non-CB1 receptor mechanisms of CBD

potentiation of THC

CBD potentiates some effects of THC in an additive or

syn-ergistic fashion Williamson (2001) has reviewed the

math-ematical definitions of synergy Wilkinson et al (2005)

provided examples of synergy within polypharmaceutical

cannabis extracts CBD may potentiate the behavioural

effects of THC via pharmacokinetic mechanisms, for

example, increasing the area under the curve of THC in blood

and brain (Klein et al., 2011) Pharmacodynamic interactions

arise when CBD and THC act at separate but interrelated

receptor sites Landmark studies demonstrating the

potentia-tion of THC by CBD or by CBD-rich cannabis extracts are

summarized in Box 1 and Box 3

We propose eight non-CB1mechanism of action by which

CBD may potentiate THC:

1 CBD inhibition of FAAH and consequential increase in

AEA may synergize with THC CB1 receptor agonism in

peripheral injury: AEA suppresses pain through a

periph-eral mechanism (Clapper et al., 2010), whereas THC works

through central CB1receptor-mediated mechanisms CBD,like cannabichromene, another cannabinoid capable ofinhibiting the putative AEA transporter, when injectedinto the periaqueductal grey area increased 2-AG levels by2.6-fold and elicited antinociception in the tail-flick test.The antinociceptive effect was blunted by antagonists of

CB1, adenosine A1 receptors and TRPA1, but not TRPV1

channels (Maione et al., 2011).

2 CBD reduces peripheral hyperalgesia via TRPV1 channels

(Costa et al., 2004) This peripheral mechanism may

hypo-thetically potentiate THC central mechanisms via CB1.Sativex provided better antinociception than THC givenalone, and the difference was likely to be mediated by

TRPV1 channels (Comelli et al., 2008).

3 CBD reduces inflammation and inflammatory cytokines(e.g TNF-α, IL-6, IL-1β) through TRPV1-, A2A- and PPARγ-mediated mechanisms (Supporting Information Appen-dix S2) THC reduces inflammation through separate CB1-and CB2receptor-mediated mechanisms

4 CBD acts as a positive allosteric modulator of glycinereceptors, which contributes to cannabis-induced analge-

sia (Xiong et al., 2011).

5 CBD is an antioxidant and ROS scavenger, more potentthan ascorbate or α-tocopherol – thus, it controls free

radical-associated diseases (Hampson et al., 1998) The U.S.

Department of Health patented this discovery (U.S Patent

No 6630507), despite its classification of cannabis as

a Schedule I substance having ‘no currently accepted

Box 2 Landmark 21st century in vivo studies of CBD functional antagonism of THC.

Animal studies

CBD antagonized THC-induced spatial memory – Fadda et al., 2004.

CBD reversed THC-induced conditioned place aversion – Vann et al., 2008.

CBD reversed THC-induced decrease in social interaction – Malone et al., 2009.

CBD increased hippocampal cell survival and neurogenesis, whereas THC has the opposite effect; the CBD response is absent in CB1 −/−

knockout mice – Wolf et al., 2010.

Human clinical trials and epidemiology studies

CBD reduced THC intoxication and impairment in binocular depth perception (a model of psychosis) – Leweke et al., 2000.

Sativexacompared to THC alone reduced adverse effects in patients with multiple sclerosis – Wade et al., 2003; Zijicek et al., 2003.

CBD counteracted THC somnolence and morning-after memory deficits – Nicholson et al., 2004.

High-THC cannabis with higher dose of CBD caused less anxiety than high-THC cannabis with lower dose of CBD – Ilan et al., 2005.

No difference in appetite and quality of life (QOL) scores between cannabis extract and THC alone – Strasser et al., 2006.

Increased CBD-to-THC ratios in chronic cannabis users inversely correlated with expression of psychotic symptoms – Morgan and Curran,2008

CBD reduced anxiety, skin conductance response and amygdala activity – the opposite of THC effects – Fusar-Poli et al., 2009.

CBD reduced ‘psychotic scores’ of THC – Bhattacharyya et al., 2010.

CBD attenuated the appetitive effects of THC – Morgan et al., 2010a.

Increased CBD-to-THC ratios in chronic cannabis users correlated with a reduction of cognitive and memory deficits – Morgan et al., 2010a Increased CBD-to-THC ratios in chronic cannabis users inversely correlated with liking for drug-related stimuli including food – Morgan et al.,

2010b

Increased CBD-to-THC ratio is associated with lower degrees of negative psychiatric symptoms – Schubart et al., 2011.

No difference in side effect profile between cannabis extract and THC alone – Karschner et al., 2011b.

Increased CBD-to-THC ratios in chronic cannabis users inversely correlated with volume loss in the hippocampus – Demirakca et al., 2011 CBD inhibited THC-elicited paranoid symptoms and hippocampal-dependent memory impairment – Englund et al., 2013.

aSativex®contains THC and CBD in a 1:1 ratio, with minor cannabinoids (5–6%), terpenoids (6–7%), sterols (6%), triglycerides, alkanes,squalene, tocopherol, carotenoids and other minor components derived from the plant material (Guy and Stott,2005)

Trang 26

medical use.’ Antioxidants limit neurological damage

fol-lowing stroke, ethanol poisoning or trauma, as well as

animal models of multiple sclerosis, Alzheimer’s,

Parkin-son’s and Huntington’s disease (Supporting Information

Appendix S2)

6 CBD suppression of ROS, TNF-α and IL-1β predictably

reduces NF-κB, which is induced by these stimuli

(Support-ing Information Appendix S2) Elevation of NF-κB occurs

in many inflammatory diseases, such as arthritis,

inflam-matory bowel disease, gastritis, asthma, atherosclerosis

and possibly schizophrenia THC may dampen NF-κB

through a CB2-mediated mechanism (Jeon et al., 1996).

THC-mediated mechanisms may diverge from

et al., 2010) CBD suppression of ROS, pro-inflammatory

cytokines and NF-κB also predictably reduces iNOS, and

consequent NO and peroxynitrite formation (Supporting

Information Appendix S2) Inhibiting iNOS helps control

chronic neurological diseases as well as cardiovascular

disease THC probably reduces iNOS through a different

mechanism (Jeon et al., 1996).

7 CBD modulation of cytosolic Ca2+levels via several

mecha-nisms (voltage-gated Ca2 + channels, mitochondrial Na+/

Ca2+ exchange, adenosine A2A and 5-HT1A receptor

agonism) is likely to contribute to its anticonvulsant

ben-efits, particularly for partial or generalized seizures (Jones

et al., 2012).

8 CBD inhibits cancer growth and induces apoptosis CBD

generates ROS and up-regulates caspase proteases

(Sup-porting Information Appendix S2) The capacity of CBD

to selectively generate ROS in cancer cells likely works

through superoxide-generating NADPH oxidases or by

inducing endoplasmic reticulum and mitochondrial stress

THC inhibition of cancer works through CB1- and CB2

receptor-mediated MAPK/ERK pathways and ceramide

accumulation Combining these mechanisms by using

THC and CBD together, produces synergistic inhibition of

cancer cell growth and apoptosis (Marcu et al., 2010).

THCV at CB1 receptors

As discussed previously, meta-analysis indicates that THCV

acts as a neutral CB1and CB2receptor antagonist, at least in

most in vitro studies Indeed, evidence has also emerged that

THCV can block CB1 receptors in vivo, as indicated by its

ability to oppose (i) anti-nociception induced by THC in themouse tail-flick test and by CP55,940 in the rat hot plate test;(ii) hypothermia induced in mice by THC; and (iii) CP55,940-

induced inhibition of rat locomotor activity (Pertwee et al., 2007; García et al., 2011).

Results from other in vivo experiments have shown that

THCV can suppress food consumption and body weight in

non-fasted mice, like AM251 (Riedel et al., 2009), and like

rimonabant, THCV can reduce signs of motor inhibition in

rats caused by 6-hydroxydopamine (García et al., 2011) It

remains to be established whether THCV produced theseeffects through CB1receptor inverse agonism or because it wascompetitively antagonizing CB1receptor-mediated effects ofone or more endogenously released endocannabinoids.However, it is noteworthy that, like the establishedneutral CB1 receptor antagonists, THCV does not share theability (i) of SR141716A or AM251 to produce signs of nausea

in rats (Rock et al., 2013) or (ii) of SR141716A to produce an

anxiogenic-like reaction in the rat light–dark immersionmodel of anxiety-like behaviour, or a suppression of saccha-rin hedonic reactions of rats in the taste reactivity test of

palatability processing (O’Brien et al., 2013) Furthermore, in some in vivo settings where neutral antagonists produce

effects, THCV does not For example, THCV did not reducefood intake and body weight in obese mice, even though itdid improve insulin resistance in these animals (Wargent

et al., 2013) Furthermore, THCV did not reduce food

deprivation-induced food intake in mice (Izzo et al., 2013).

THCV has anti-epileptiform actions in the rat

pentylene-tetrazole seizure model (Hill et al., 2010) This is in contrast to

rimonabant safety data, where seizures were occasionally

observed (Bermudez-Silva et al., 2010) Rimonabant

signifi-cantly increased seizure duration and seizure frequency in the

rat pilocarpine model of epilepsy (Wallace et al., 2003)

Pro-convulsant effects were also observed with AM251 in a model

of generalized seizures (Shafaroodi et al., 2004).

Also, when given in vivo at doses well above those at

which it can block CB1receptors, THCV produces signs of CB1

receptor activation For example, in experiments performedwith mice, THCV has been shown to induce (i) immobility in

Box 3 Landmark 21st century studies of CBD potentiating the effects of THC.

Animal studies

CBD potentiated THC antinociception – Varvel et al., 2006.

CBD enhanced THC tetrad effects – Hayakawa et al., 2008.

CBD turned an ineffective THC dose into an effective one in colitis – Jamontt et al., 2010.

CBD altered THC pharmacokinetics and augments some THC behavioural effects – Klein et al., 2011.

Sativex compared to THC alone enhanced antinociception in a rat model of neuropathic pain – Comelli et al., 2008.

Human clinical trials and epidemiology studies

CBD plus THC imparted synergistic inhibition of human glioblastoma cancer cell growth and apoptosis – Marcu et al., 2010.

Sativexacompared to THC alone provides greater pain relief and improvement in sleep – Notcutt et al., 2004.

Sativexacompared to THC extract reduced cancer-related pain – Johnson et al., 2010.

Sativexacompared to THC alone reduced abnormalities in psychomotor performance associated with schizophrenia – Roser et al., 2009.

aSativex®contains THC and CBD in a 1:1 ratio, with minor cannabinoids (5–6%), terpenoids (6–7%), sterols (6%), triglycerides, alkanes,squalene, tocopherol, carotenoids and other minor components derived from the plant material (Guy and Stott, 2005)

Trang 27

the Pertwee ring test, albeit with a potency 4.8 times less than

that of THC, and (ii) anti-nociception in the tail-flick test

(Gill et al., 1970; Pertwee et al., 2007) Importantly, although

SR141716A was found to antagonize the antinociceptive

effect of THCV, it did not give rise to any significant

antago-nism of THCV-induced hypothermia or ring immobility

(Pertwee et al., 2007) THCV also decreased pain behaviour in

the formalin test; this effect appeared to be CB1 and CB2

receptor-mediated (Bolognini et al., 2010) It remains to be

established how THCV produces apparent CB1receptor

acti-vation in vivo but not in vitro at doses above those at which it

can block CB1receptors both in vivo and in vitro One

possi-bility is the apossi-bility of THCV to inhibit endocannabinoid

re-uptake (see previous discussion), with indirect activation

of cannabinoid receptors Models of intestinal transit are

often used as assays of CB1 receptor activation and THCV

inhibits upper intestinal transit in a dose-dependent manner

(Izzo et al., 2013) However, this effect was not antagonized

by a dose of rimonabant inactive per se This study, together

with the hypothermia and immobility assay, indicates that

THCV can have cannabimimetic effects, which appear to be

independent of the CB1receptor

The ‘abants’ were withdrawn from the market because of

their worsening of anxiety and depression in obese patients

In contrast, THCV has very little effect in animal models of

anxiety and depression For example, the dose of THCV

required to impart anxiogenic effects in the elevated plus

maze is 30-fold higher than that of rimonabant (Izzo et al.,

2013)

The observed similarities or differences between THCV and

rimonabant (Box 4) may depend upon several factors These

include (i) the initial physiopathological status of the cell/

tissue/organ, and the degree of expression therein of

func-tional CB1 receptors, which might affect the activity of

different ligands of the same receptor in different manners; (ii)

the presence or absence in the cell/tissue/organ of non-CB1,

non-CB2receptor targets for THCV – in particular, TRP

chan-nels and CB2receptors, particularly when THCV is

adminis-tered at doses higher than those required for CB1 receptor

antagonism, might counteract some of the CB1 receptor

antagonism-mediated effects of THCV, but not others; (iii) the

fact that at higher doses, THCV might start behaving as a CB1

receptor agonist, thus clearly counteracting some of the effects

due to CB1receptor neutral antagonism; (iv) different

pharma-cokinetic properties of the two compounds, particularly, but

not limited to, under pathological conditions that may altertheir tissue distribution and catabolism

Conclusions

Based upon the meta-analysis of in vitro data, and in vivo data

cited in the Discussion section, we conclude that the cology of neither CBD nor THCV has much in common withthat of the ‘abants’ and of rimonabant in particular WhileCBD does counteract some of the actions of THC, particularly

pharma-in the brapharma-in, it potentiates other actions of THC The capacity

of CBD to modulate several signalling systems and to enhanceendocannabinoid levels might produce varying effects on theendocannabinoid system and CB1 receptors This may beorgan/tissue/cell-dependent, and unlikely due to directmolecular interactions with CB1receptors

Although THCV undoubtedly behaves as a CB1(and CB2)receptor orthosteric ligand in binding assays, and as a neutral

CB1 receptor antagonist in functional assays, its

pharmaco-logical profile in vivo overlaps only in part with that of

rimonabant and other CB1receptor inverse agonists, or evenwith that of synthetic CB1receptor neutral antagonists.Thus, CBD and THCV represent the two opposing ends ofactivity at CB1receptors: a low-affinity CB1 receptor ligand,which can affect CB1 receptor activity in vivo in an indirect

manner, and a high-affinity CB1receptor ligand and potent

antagonist in vitro, which instead produces CB1 receptor

antagonism-mediated effects in vivo only in a few instances These paradoxical examples of how in vivo pharmacology is not always predicted from in vitro mechanistic studies under- lie the necessity of testing compounds in vivo before drawing

any conclusion on their functional activity at a given target.This is especially true regarding compounds that havecomplex pharmacology, such as the phytocannabinoids.However, it must be remembered that whether or not

in vitro mechanistic studies predict in vivo pharmacology

depends, in part, upon pharmacokinetic data – particularly

on the ability of CBD and THCV to reach concentrations in

plasma and tissues similar to the concentrations shown in

vitro to be necessary to interact with certain targets In mice,

the plasma Cmaxof THCV, given at a dose of 30 mg·kg−1eitherp.o or i.p., was 0.24 and 0.88 mg·L−1, and thus lower thanthat of a higher dose of CBD (120 mg·kg−1), which was 2.2and 14.3 mg·L−1(Deiana et al., 2012) A similar scenario was

Box 4 Landmark 21st century in vivo studies concerning THCV.

THCV induced anti-nociception in the tail-flick test – Pertwee et al., 2007.

THCV suppressed food consumption and body weight in non-fasted mice – Riedel et al., 2009.

THCV antagonized the antinociceptive effects of THC in the rat acetic acid model of visceral nociception – Booker et al., 2009.

THCV exerted anticonvulsant actions in the PTZ model of seizure – Hill et al., 2010.

THCV reduced pain behaviour in the formalin test – Bolognini et al., 2010.

THCV imparted neuroprotective effects and relieves symptoms in rat models of Parkinson’s disease – García et al., 2011.

THCV did not produce nausea or a suppression of saccharin hedonic reactions of rats in the taste reactivity test of palatability processing – Rock

et al., 2013.

THCV did not reduce food intake and body weight in obese mice – Wargent et al., 2013.

THCV did not produce an anxiogenic-like reaction in the rat light–dark immersion model of anxiety-like behaviour – O’Brien et al., 2013.

Trang 28

described by the same authors also for the brain, although in

this case the difference between THCV and CBD was less

striking, with the Cmax of the former being 0.43 and

1.69μm·g−1and that of CBD being 1.3 and 6.9μm·g−1

In rats, two different vehicles were compared for CBD

(120 mg·kg−1), and the plasma Cmax values were 2 and

2.6 mg·L−1after p.o and i.p administration, respectively, for

cremophor, and 3.2 and 2.4 mg·L−1 for solutol Brain Cmax

values were 8.6 and 6.8μm·g−1after p.o and i.p

administra-tion, respectively, for cremophor, and 12.6 and 5.2μm·g−1for

solutol Rat pharmacokinetic values for THCV (30 mg·kg−1)

were Cmax0.21 and 0.4 mg mL−1for p.o and i.p

administra-tion, respectively, in plasma, and 0.3 and 1.62μm·g−1for oral

and i.p administration, respectively, in the brain Thus, there

are only small differences between the two species, for the

two compounds

No human studies have been published regarding THCV

pharmacokinetics Human subjects given Sativex as a buccal

spray (THC 16.2 mg and CBD 15.0 mg) averaged a CBD Cmax

plasma concentration of 6.7μg·L−1, range 2.0–20.5μg·L−1

(Karschner et al., 2011a) The metabolism of THC

adminis-tered as Sativex was slightly aladminis-tered, as they observed lower

11-OH-THC Cmaxafter Sativex in relation to 15 mg p.o THC

(falling short of significance, P= 0.09) Subjects given eightbuccal sprays of Sativex per day (= 20 mg CBD daily) over 9days averaged CBD plasma concentration of 3.2 ng·mL−1

(Stott et al., 2013).

Thus, given these low Cmaxvalues, many in vitro studies

reporting effects in the micromolar range, especially for CBD,might be regarded as irrelevant Yet, in the clinic, both CBDand THCV, like rimonabant, are likely to be administeredchronically and their tissue concentrations are therefore likely

to accumulate Furthermore, it must be emphasized that a per comparison between the pharmacokinetics and bioavail-ability of CBD or THCV with those of rimonabant and other

pro-‘abants’ cannot be made as data for the latter are scant andmostly unpublished possibly because these compounds arestill proprietary and their development has been interrupted

Figure 2

Algorithm for investigating cannabinoids in mechanistic studies Dashed arrow: Note that in some cases compounds that do not enhance the

binding of high affinity ligands to their receptors might still be allosteric modulators (May et al., 2007).

Trang 29

At any rate, much of the confusion about CBD as a

‘rimonabant-like drug’ might have been avoided if one had

followed the algorithm shown in Figure 2 to decide whether,

based upon in vitro pharmacological data, a substance can be

described as a CB1receptor orthosteric ligand first and then as

agonist, inverse agonist, neutral antagonist or functionally

inactive (Figure 2) Indeed, based upon this algorithm, one

might even question the necessity of testing compounds in

functional assays of a given receptor in vitro if they do not

exhibit high affinity in radioligand displacement assays for

that receptor An exception to this rule might be allosteric

ligands, which cannot always be identified by the binding

assays normally used to evaluate the affinity of compounds

for GPCRs (May et al., 2007).

Our results may have important effects on the future

clinical development of CBD as an antipsychotic,

anti-inflammatory and anti-epileptic drug, and of THCV for the

treatment of type 2 diabetes Meta-analysis suggests that

these two phytocannabinoids are very unlikely to produce

the central adverse events typical of THC, as well as the

central adverse events of the ‘abants’

Acknowledgements

This work was partially supported by an unrestricted grant

from GW Pharmaceuticals, Salisbury, UK We thank all the

scientists who responded to our queries regarding their

unpublished results

Conflict of interest

M D is an employee of GW Pharmaceuticals, UK J M M., V

D and R P are consultants for, and receive research funds

from, GW Pharmaceuticals, UK

References

Alexander SPH, Benson HE, Faccenda E, Pawson AJ, Sharman JL,

Spedding M et al (2013a) The Concise Guide to PHARMACOLOGY

2013/14: G Protein-Coupled Receptors Br J Pharmacol 170:

1459–1581

Alexander SPH, Benson HE, Faccenda E, Pawson AJ, Sharman JL,

Spedding M et al (2013b) The Concise Guide to PHARMACOLOGY

2013/14: Enzymes Br J Pharmacol 170: 1797–1867

Alexander SPH, Benson HE, Faccenda E, Pawson AJ, Sharman JL,

Catterall WA et al (2013c) The Concise Guide to

PHARMACOLOGY 2013/14: Ion Channels Br J Pharmacol 170:

1607–1651

Alexander SPH, Benson HE, Faccenda E, Pawson AJ, Sharman JL,

Spedding M et al (2013d) The Concise Guide to PHARMACOLOGY

2013/14: Transporters Br J Pharmacol 170: 1706–1796

Alexander SPH, Benson HE, Faccenda E, Pawson AJ, Sharman JL,

Catterall WA et al (2013e) The Concise Guide to

PHARMACOLOGY 2013/14: Ligand-Gated Ion Channels

Br J Pharmacol 170: 1582–1606

Alexander SPH, Benson HE, Faccenda E, Pawson AJ, Sharman JL,

Spedding M et al (2013f) The Concise Guide to PHARMACOLOGY

2013/14: Nuclear Hormone Receptors Br J Pharmacol 170:

1652–1675

Bayewitch M, Rhee MH, Avidor-Reiss T, Breuer A, Mechoulam R,Vogel Z (1996) (-)-delta9-tetrahydrocannabinol antagonizes theperipheral cannabinoid receptor-mediated inhibition of adenylylcyclase J Biol Chem 271: 9902–9905

Bermudez-Silva FJ, Viveros MP, McPartland JM,Rodriguez de Fonseca F (2010) The endocannabinoid system,eating behavior and energy homeostasis: the end or a newbeginning? Pharmacol Biochem Behav 95: 375–382

Bhattacharyya S, Morrison PD, Fusar-Poli P, Martin-Santos R,

Borgwardt S, Winton-Brown T et al (2010) Opposite effects of

delta-9-tetrahydrocannabinol and cannabidiol on human brainfunction and psychopathology Neuropsychopharmacology 35:764–774

Bolognini D, Costa B, Maione S, Comelli F, Marini P, Di Marzo V

et al (2010) The plant cannabinoidΔ9-tetrahydrocannabivarin candecrease signs of inflammation and inflammatory pain in mice

Br J Pharmacol 160: 677–687

Booker L, Naidu PS, Razdan RK, Mahadevan A, Lichtman AH(2009) Evaluation of prevalent phytocannabinoids in the aceticacid model of visceral nociception Drug Alcohol Depend 105:42–47

Browne RG, Weissman A (1981) Discriminative stimulus properties

of delta 9-tetrahydrocannabinol: mechanistic studies J ClinPharmacol 21: 227S–234S

Campos AC, Guimaraes FS (2008) Involvement of 5HT1A receptors

in the anxiolytic-like effects of cannabidiol injected into thedorsolateral periaqueductal gray of rats Psychopharmacology (Berl)199: 223–230

Campos AC, Guimaraes FS (2009) Evidence for a potential role forTRPV1 receptors in the dorsolateral periaqueductal gray in theattenuation of the anxiolytic effects of cannabinoids ProgNeuropsychopharmacol Biol Psychiatry 33: 1517–1521

Campos AC, de Paula Soares V, Carvalho MC, Ferreira FR, Vicente

MA, Brandão ML et al (2013) Involvement of serotonin-mediated

neurotransmission in the dorsal periaqueductal gray matter oncannabidiol chronic effects in panic-like responses in rats

Psychopharmacology (Berl) 226: 13–24

Campos AC, Ortega Z, Palazuelos J, Fogaça MV, Aguiar DC,

Díaz-Alonso J et al (2013) The anxiolytic effect of cannabidiol on

chronically stressed mice depends on hippocampal neurogenesis:involvement of the endocannabinoid system Int J

Neuropsychopharmacol 16: 1407–1419

Castillo A, Tolón MR, Fernández-Ruiz J, Romero J, Martinez-Orgado

J (2010) The neuroprotective effect of cannabidiol in an in vitromodel of newborn hypoxic-ischemic brain damage in mice ismediated by CB(2) and adenosine receptors Neurobiol Dis 37:434–440

Cawthorne M, Stott C, Wright S, Guy G, Zaibi M, Wargent E(2008) The metabolic effects of tetrahydrocannabivarin (THCV)and cannabidiol (CBD) Proceedings of the 18th AnnualSymposium on the Cannabinoids International CannabinoidResearch Society, Burlington, VT, p 42

Clapper JR, Moreno-Sanz G, Russo R, Guijarro A, Vacondio F,

Duranti A et al (2010) Anandamide suppresses pain initiation

through a peripheral endocannabinoid mechanism Nat Neurosci13: 1265–1270

Trang 30

Cocchetto DM, Cook LF, Cato AE (1981) A critical review of the

safety and antiemetic efficacy of delta-9-tetrahydrocannabinol

Drug Intell Clin Pharm 15: 867–875

Comelli F, Giagnoni G, Bettoni I, Colleoni M, Costa B (2008)

Antihyperalgesic effect of a Cannabis sativa extract in a rat model of

neuropathic pain: mechanisms involved Phytother Res 22:

1017–1024

Costa B, Giagnoni G, Franke C, Trovato AE, Colleoni M (2004)

Vanilloid TRPV1 receptor mediates the antihyperalgesic effect of the

nonpsychoactive cannabinoid, cannabidiol, in a rat model of acute

inflammation Br J Pharmacol 143: 247–250

De Petrocellis L, Ligresti A, Moriello AS, Allarà M, Bisogno T,

Petrosino S et al (2011) Effects of cannabinoids and

cannabinoid-enriched Cannabis extracts on TRP channels and

endocannabinoid metabolic enzymes Br J Pharmacol 163:

1479–1494

Deiana S, Watanabe A, Yamasaki Y, Amada N, Arthur M, Fleming S

et al (2012) Plasma and brain pharmacokinetic profile of

cannabidiol (CBD), cannabidivarine (CBDV),

Δ9-tetrahydrocannabivarin (THCV) and cannabigerol (CBG) in rats

and mice following oral and intraperitoneal administration and

CBD action on obsessive-compulsive behaviour

Psychopharmacology (Berl) 219: 859–873

Demirakca T, Sartorius A, Ende G, Meyer N, Welzel H, Skopp G

et al (2011) Diminished gray matter in the hippocampus of

cannabis users: possible protective effects of cannabidiol Drug

Alcohol Depend 114: 242–245

Devane WA, Dysarz FA 3rd, Johnson MR, Melvin LS, Howlett AC

(1988) Determination and characterization of a cannabinoid

receptor in rat brain Mol Pharmacol 34: 605–613

Di Marzo V (2008) Targeting the endocannabinoid system: to

enhance or reduce? Nat Rev Drug Discov 7: 438–455

Di Marzo V (2010) Anandamide serves two masters in the brain

Nat Neurosci 13: 1446–1448

Di Marzo V, Melck D, Bisogno T, De Petrocellis L (1998)

Endocannabinoids: endogenous cannabinoid receptor ligands with

neuromodulatory action Trends Neurosci 21: 521–528

Di Marzo V, De Petrocellis L, Fezza F, Ligresti A, Bisogno T (2002)

Anandamide receptors Prostaglandins Leukot Essent Fatty Acids 66:

377–391

El Yacoubi M, Ledent C, Ménard JF, Parmentier M, Costentin J,

Vaugeois JM (2000) The stimulant effects of caffeine on locomotor

behaviour in mice are mediated through its blockade of adenosine

A(2A) receptors Br J Pharmacol 129: 1465–1473

Englund A, Morrison PD, Nottage J, Hague D, Kane F, Bonaccorso S

et al (2013) Cannabidiol inhibits THC-elicited paranoid

symptoms and hippocampal-dependent memory impairment

J Psychopharmacol 27: 19–27

Fadda P, Robinson L, Fratta W, Pertwee RG, Riedel G (2004)

Differential effects of THC- or CBD-rich cannabis extracts on

working memory in rats Neuropharmacology 47: 1170–1179

Fusar-Poli P, Crippa JA, Bhattacharyya S, Borgwardt SJ, Allen P,

Martin-Santos R et al (2009) Distinct effects of

delta-9-tetrahydrocannabinol and cannabidiol on neural activation

during emotional processing Arch Gen Psychiatry 66: 95–105

Gaoni Y, Mechoulam R (1964) Isolation, structure, and partial

synthesis of an active constituent of hashish J Am Chem Soc 86:

1646–1647

García C, Palomo-Garo C, Garcia-Arencibia M, Ramos JA, Pertwee

RG, Fernandez-Ruiz J (2011) Symptom-relieving and

neuroprotective effects of the phytocannabinoidΔ9-THCV inanimal models of Parkinson’s disease Br J Pharmacol 163:1495–1506

Gill EW, Paton WDM, Pertwee RG (1970) Preliminary experiments

on the chemistry and pharmacology of Cannabis Nature 228:

Gomes FV, Del Bel EA, Guimarães FS (2013) Cannabidiolattenuates catalepsy induced by distinct pharmacologicalmechanisms via 5-HT1A receptor activation in mice ProgNeuropsychopharmacol Biol Psychiatry 46: 43–47

Grinspoon L, Bakalar JB (1997) Marihuana, the ForbiddenMedicine Yale University Press: New Haven, CT

Guy GW, Stott CG (2005) The development of Sativex – a naturalcannabis-based medicine In: Mechoulam R (ed.) Cannabinoids asTherapeutics Birkhäuser Verlag: Basel, pp 231–263

Hampson AJ, Grimaldi M, Axelrod J, Wink D (1998) Cannabidioland (-)Delta9-tetrahydrocannabinol are neuroprotective

antioxidants Proc Natl Acad Sci U S A 95: 8268–8273

Hanuš L (2008) Pharmacological and therapeutic secrets of plantand brain (endo)cannabinoids Med Res Rev 29: 213–271

Hayakawa K, Mishima K, Hazekawa M, Sano K, Irie K, Orito K et al.

(2008) Cannabidiol potentiates pharmacological effects ofDelta(9)-tetrahydrocannabinol via CB(1) receptor-dependentmechanism Brain Res 1188: 157–164

Higgins JPT, Green S (2005) Cochrane Handbook for SystematicReviews of Interventions 4.2.5 John Wiley & Sons: Chichester, UK

Hill AJ, Weston SE, Jones NA, Smith I, Bevan SA, Williamson EM

et al (2010).Δ9-Tetrahydrocannabivarin suppresses in vitroepileptiform and in vivo seizure activity in adult rats Epilepsia 51:1522–1532

Hollister LE (1973) Cannabidiol and cannabinol in man

Ilan AB, Gevins A, Coleman M, ElSohly MA, de Wit H (2005).Neurophysiological and subjective profile of marijuana withvarying concentrations of cannabinoids Behav Pharmacol 16:487–496

Izzo AA, Borrelli F, Capasso R, Di Marzo V, Mechoulam R (2009).Non-psychotropic plant cannabinoids: new therapeutic

opportunities from an ancient herb Trends Pharmacol Sci 30:515–527

Izzo AA, Zaibi MS, Wargent E, Capasso R, Arbuckle C, Duncan M

et al (2013) The effect ofΔ9-tetrahydrocannabivarin on fooddeprivation-induced food intake and upper gastrointestinalmotility: differences from rimonabant Proceedings of the 7thConference on Cannabinoids in Medicine InternationalAssociation for Cannabis as Medicine, Köln, p 57

Trang 31

Jamontt JM, Molleman A, Pertwee RG, Parsons ME (2010) The

effects of Delta-tetrahydrocannabinol and cannabidiol alone and in

combination on damage, inflammation and in vitro motility

disturbances in rat colitis Br J Pharmacol 160: 712–723

Järbe TU, Henriksson BG, Ohlin GC (1977) Delta9-THC as a

discriminative cue in pigeons: effects of delta8-THC, CBD, and

CBN Arch Int Pharmacodyn Ther 228: 68–72

Jeon YJ, Yang KH, Pulaski JT, Kaminski NE (1996) Attenuation of

inducible nitric oxide synthase gene expression by delta

9-tetrahydrocannabinol is mediated through the inhibition of

nuclear factor- kappa B/Rel activation Mol Pharmacol 50: 334–341

Johnson JR, Burnell-Nugent M, Lossignol D, Ganae-Motan ED, Potts

R, Fallon MT (2010) Multicenter, double-blind, randomized,

placebo-controlled, parallel-group study of the efficacy, safety, and

tolerability of THC:CBD extract and THC extract in patients with

intractable cancer-related pain J Pain Symptom Manage 39:

167–179

Jones NA, Glyn SE, Akiyama S, Hill TD, Hill AJ, Weston SE et al.

(2012) Cannabidiol exerts anti-convulsant effects in animal models

of temporal lobe and partial seizures Seizure 21: 344–352

Karschner EL, Darwin WD, Goodwin RS, Wright S, Huestis MA

(2011a) Plasma cannabinoid pharmacokinetics following controlled

oral delta9-tetrahydrocannabinol and oromucosal cannabis extract

administration Clin Chem 57: 66–75

Karschner EL, Darwin WD, McMahon RP, Liu F, Wright S, Goodwin

RS et al (2011b) Subjective and physiological effects after

controlled Sativex and oral THC administration Clin Pharmacol

Ther 89: 400–407

Klein C, Karanges E, Spiro A, Wong A, Spencer J, Huynh T et al.

(2011) Cannabidiol potentiatesΔ9-tetrahydrocannabinol (THC)

behavioural effects and alters THC pharmacokinetics during acute

and chronic treatment in adolescent rats Psychopharmacology

(Berl) 218: 443–457

Kozak KR, Crews BC, Morrow JD, Wang LH, Ma YH, Weinander R

et al (2002) Metabolism of the endocannabinoids,

2-arachidonylglycerol and anandamide, into prostaglandin,

thromboxane, and prostacyclin glycerol esters and ethanolamides

J Biol Chem 277: 44877–44885

Kozela E, Pietr M, Juknat A, Rimmerman N, Levy R, Vogel Z (2010)

Cannabinoids delta(9)-tetrahydrocannabinol and cannabidiol

differentially inhibit the lipopolysaccharide-activated NF-kappaB

and interferon-beta/STAT proinflammatory pathways in BV-2

microglial cells J Biol Chem 285: 1616–1626

Lerner TN, Horne EA, Stella N, Kreitzer AC (2010)

Endocannabinoid signaling mediates psychomotor activation by

adenosine A2A antagonists J Neurosci 30: 2160–2164

Leweke FM, Schneider U, Radwan M, Schmidt E, Emrich HM

(2000) Different effects of nabilone and cannabidiol on binocular

depth inversion in man Pharmacol Biochem Behav 66: 175–181

Leweke FM, Piomelli D, Pahlisch F, Muhl D, Gerth CW, Hoyer C

et al (2012) Cannabidiol enhances anandamide signaling and

alleviates psychotic symptoms of schizophrenia Transl Psychiatry

2: e94

Liberati A, Altman DG, Tetzlaff J, Mulrow C, Gotzsche PC et al.

(2009) The PRISMA statement for reporting systematic reviews and

meta-analyses of studies that evaluate health care interventions:

explanation and elaboration PLoS Med 6: e1000100

Ligresti A, Schiano Moriello A, Starowicz K, Matias I, Pisanti S,

De Petrocellis L et al (2006) Antitumor activity of plant

cannabinoids with emphasis on the effect of cannabidiol onhuman breast carcinoma J Pharmcol Exp Ther 318: 1375–1387.Loewe WS, Modell W (1941) The action of chemical components

of cannabis extracts J Pharmacol Exp Ther 72: 27

Long LE, Chesworth R, Huang XF, McGregor IS, Arnold JC, Karl T(2010) A behavioural comparison of acute and chronic

D9-tetrahydrocannabinol and cannabidiol in C57BL/6JArc mice Int

J Neuropsychopharmacol 13: 861–876

Maione S, Piscitelli F, Gatta L, Vita D, De Petrocellis L, Palazzo E

et al (2011) Non-psychoactive cannabinoids modulate the

descending pathway of antinociception in anaesthetized ratsthrough several mechanisms of action Br J Pharmacol 162:584–596

Malone DT, Jongejan D, Taylor DA (2009) Cannabidiol reverses thereduction in social interaction produced by low dose

Delta(9)-tetrahydrocannabinol in rats Pharmacol Biochem Behav93: 91–96

Marcu JP, Christian RT, Lau D, Zielinski AJ, Horowitz MP, Lee J

et al (2010) Cannabidiol enhances the inhibitory effects of

delta9-tetrahydrocannabinol on human glioblastoma cellproliferation and survival Mol Cancer Ther 9: 180–189

Martire A, Tebano MT, Chiodi V, Ferreira SG, Cunha RA, Köfalvi A

et al (2011) Pre-synaptic adenosine A2A receptors control

cannabinoid CB1 receptor-mediated inhibition of striatalglutamatergic neurotransmission J Neurochem 116: 273–280.May LT, Leach K, Sexton PM, Christopoulous A (2007) Allostericmodulation of G protein-coupled receptors Annu Rev PharmacolToxicol 47: 1–51

McPartland JM, Guy G (2004) The evolution of Cannabis and

coevolution with the cannabinoid receptor – a hypothesis In: Guy

G, Robson R, Strong K, Whittle B (eds) The Medicinal Use ofCannabis Royal Society of Pharmacists: London, pp 71–102.McPartland JM, Pruitt PL (1999) Side effects of pharmaceuticals notelicited by comparable herbal medicines: the case of

tetrahydrocannabinol and marijuana Altern Ther Health Med 5:57–62

McPartland JM, Russo EB (2001) Cannabis and cannabis extracts:

greater than the sum of their parts? J Cannabis Therapeutics 1:103–132

McPartland JM, Glass M, Pertwee RG (2007) Meta-analysis ofcannabinoid ligand binding affinity and receptor distribution:interspecies differences Br J Pharmacol 152: 583–593

Mechoulam R, Fride E, Di Marzo V (1998) Endocannabinoids.Eur J Pharmacol 359: 1–18

Mechoulam R, Peters M, Murillo-Rodriguez E, Hanuš LO (2007).Cannabidiol – recent advances Chem Biodivers 4: 1678–1692

de Meijer EPM, Bagatta M, Carboni A, Crucitti P,

Cristiana Moliterni VM, Ranalli P et al (2003) The inheritance of chemical phenotype in Cannabis sativa L Genetics 163: 335–346.

Morgan CJ, Curran HV (2008) Effects of cannabidiol onschizophrenia-like symptoms in people who use cannabis

Br J Psychiatry 192: 306–307

Morgan CJ, Freeman TP, Schafer GL, Curran HV (2010a)

Cannabidiol attenuates the appetitive effects of delta9-tetrahydrocannabinol in humans smoking their chosen cannabis.Neuropsychopharmacology 35: 1879–1885

Morgan CJ, Schafer G, Freeman TP, Curran HV (2010b) Impact ofcannabidiol on the acute memory and psychotomimetic effects ofsmoked cannabis: naturalistic study Br J Psychiatry 197: 285–290

Trang 32

Nicholson AN, Turner C, Stone BM, Robson PJ (2004) Effect of

delta-9-tetrahydrocannabinol and cannabidiol on nocturnal sleep

and early-morning behavior in young adults J Clin

Psychopharmacol 24: 305–313

Notcutt W, Price M, Miller R, Newport S, Phillips C, Simmons S

et al (2004) Initial experiences with medicinal extracts of cannabis

for chronic pain: results from 34 ‘N of 1’ studies Anaesthesia 59:

440–452

O’Brien LD, Wills KL, Segsworth B, Dashney B, Rock EM, Limebeer

CL et al (2013) Effect of chronic exposure to rimonabant and

phytocannabinoids on anxiety-like behavior and saccharin

palatability Pharmacol Biochem Behav 103: 597–602

Palazzo E, de Novellis V, Petrosino S, Marabese I, Vita D, Giordano

C et al (2006) Neuropathic pain and the endocannabinoid system

in the dorsal raphe: pharmacological treatment and interactions

with the serotonergic system Eur J Neurosci 24: 2011–2020

Pawson AJ, Sharman JL, Benson HE, Faccenda E, Alexander SP,

Buneman OP et al.; NC-IUPHAR (2014) The IUPHAR/BPS Guide to

PHARMACOLOGY: an expert-driven knowledge base of drug targets

and their ligands Nucl Acids Res 42 (Database Issue):

D1098–1106

Pertwee RG (2004) The pharmacology and therapeutic potential of

cannabidiol In: Di Marzo V (ed.) Cannabinoids Kluwer

Academic/Plenum Publishers: New York, pp 32–83

Pertwee RG (2005) The therapeutic potential of drugs that target

cannabinoid receptors or modulate the tissue levels or actions of

endocannabinoids AAPS J 7: E625–E654

Pertwee RG (2008) The diverse CB1 and CB2 receptor

pharmacology of three plant cannabinoids:

delta9-tetrahydrocannabinol, cannabidiol and

delta9-tetrahydrocannabivarin Br J Pharmacol 153: 199–215

Pertwee RG, Thomas A, Stevenson LA, Ross RA, Varvel SA,

Lichtman AH et al (2007) The psychoactive plant cannabinoid,

Δ9-tetrahydrocannabinol, is antagonized byΔ8- and

Δ9-tetrahydrocannabivarin in mice in vivo Br J Pharmacol 150:

586–594

Pertwee RG, Howlett AC, Abood ME, Alexander SP, Di Marzo V,

Elphick MR et al (2010) International Union of Basic and Clinical

Pharmacology LXXIX Cannabinoid receptors and their ligands:

beyond CB1and CB2 Pharmacol Rev 62: 588–631

Petitet F, Jeantaud B, Reibaud M, Imperato A, Dubroeucq MC

(1998) Complex pharmacology of natural cannabinoids: evidence

for partial agonist activity of delta9-tetrahydrocannabinol and

antagonist activity of cannabidiol on rat brain cannabinoid

receptors Life Sci 63: PL1–PL6

Qin N, Neeper MP, Liu Y, Hutchinson TL, Lubin ML, Flores CM

(2008) TRPV2 is activated by cannabidiol and mediates CGRP

release in cultured rat dorsal root ganglion neurons J Neuroscience

28: 6231–6238

Reed GF, Lynn F, Meade BD (2002) Use of coefficient of variation

in assessing variability of quantitative assays Clin Diagn Lab

Immunol 9: 1235–1239

Rhee MH, Vogel Z, Barg J, Bayewitch M, Levy R, Hanus L et al.

(1997) Cannabinol derivatives: binding to cannabinoid receptors

and inhibition of adenylylcyclase J Med Chem 40: 3228–3233

Riedel G, Fadda P, McKillop-Smith S, Pertwee RG, Platt B, Robinson

L (2009) Synthetic and plant-derived cannabinoid receptor

antagonists show hypophagic properties in fasted and non-fasted

mice Br J Pharmacol 156: 1154–1166

Rock EM, Sticht MA, Duncan M, Stott C, Parker LA (2013).Evaluation of the potential of the phytocannabinoids,cannabidivarin (CBDV) andΔ9-tetrahydrocannabivarin (THCV), toproduce CB1 receptor inverse agonism symptoms of nausea in rats

Br J Pharmacol 170: 671–678

Roser P, Gallinat J, Weinberg G, Juckel G, Gorynia I, Stadelmann

AM (2009) Psychomotor performance in relation to acute oraladministration of Delta9-tetrahydrocannabinol and standardizedcannabis extract in healthy human subjects Eur Arch PsychiatryClin Neurosci 259: 284–292

Russo E, Guy GW (2006) A tale of two cannabinoids: thetherapeutic rationale for combining tetrahydrocannabinol andcannabidiol Med Hypotheses 66: 234–246

Russo EB (2004) Clinical endocannabinoid deficiency (CECD): canthis concept explain therapeutic benefits of cannabis in migraine,fibromyalgia, irritable bowel syndrome and other

treatment-resistant conditions? Neuro Endocrinol Lett 25: 31–39.Russo EB (2011) Taming THC: potential cannabis synergy andphytocannabinoid-pterpenoid entourage effects Br J Pharmacol163: 1344–1364

Sagredo O, Pazos MR, Satta V, Ramos JA, Pertwee RG,Fernández-Ruiz J (2011) Neuroprotective effects ofphytocannabinoid-based medicines in experimental models ofHuntington’s disease J Neurosci Res 89: 1509–1518

Savinainen JR, Saario SM, Niemi R, Järvinen T, Laitinen JT (2003)

An optimized approach to study endocannabinoid signaling:evidence against constitutive activity of rat brain adenosine A1 andcannabinoid CB1 receptors Br J Pharmacol 140: 1451–1459.Schubart CD, Sommer IE, van Gastel WA, Goetgebuer RL, Kahn RS,Boks MP (2011) Cannabis with high cannabidiol content isassociated with fewer psychotic experiences Schizophr Res 130:216–221

Shafaroodi H, Samini M, Moezi L, Homayoun H, Sadeghipour H,

Tavakoli S et al (2004) The interaction of cannabinoids and

opioids on pentylenetetrazole-induced seizure threshold in mice.Neuropharmacology 47: 390–400

Stott CG, White L, Wright S, Wilbraham D, Guy GW (2013) Aphase I study to assess the single and multiple dose

pharmacokinetics of THC/CBD oromucosal spray Eur J ClinPharmacol 69: 1135–1147

Strasser F, Luftner D, Possinger K, Ernst G, Ruhstaller T, Meissner W

et al (2006) Comparison of orally administered cannabis extract

and delta-9-tetrahydrocannabinol in treating patients withcancer-related anorexia-cachexia syndrome: a multicenter, phase III,randomized, double-blind, placebo-controlled clinical trial from theCannabis-In-Cachexia-Study-Group J Clin Oncol 24: 3394–3400.Vann RE, Gamage TF, Warner JA, Marshall EM, Taylor NL, Martin

BR et al (2008) Divergent effects of cannabidiol on the

discriminative stimulus and place conditioning effects ofDelta(9)-tetrahydrocannabinol Drug Alcohol Depend 94: 191–198.Varvel SA, Wiley JL, Yang R, Bridgen DT, Long K, Lichtman AH

et al (2006) Interactions between THC and cannabidiol in mouse

models of cannabinoid activity Psychopharmacology (Berl) 186:226–234

Wade DT, Robson P, House H, Makela P, Aram J (2003) Apreliminary controlled study to determine whether whole-plantcannabis extracts can improve intractable neurogenic symptoms.Clin Rehabil 17: 21–29

Wallace MJ, Blair RE, Falenski KW, Martin BR, DeLorenzo RJ (2003).The endogenous cannabinoid system regulates seizure frequencyand duration in a model of temporal lobe epilepsy J PharmacolExp Ther 307: 129–137

Trang 33

Wargent ET, Zaibi MS, Silvestri C, Hislop DC, Stocker CJ, Stott CG

et al (2013) The cannabinoidΔ(9)-tetrahydrocannabivarin (THCV)

ameliorates insulin sensitivity in two mouse models of obesity

Nutr Diabetes 3: e68

Wilkinson JD, Whalley BJ, Baker D, Pryce G, Constanti A, Gibbons

S et al (2005) Medicinal cannabis: is delta9-tetrahydrocannabinol

necessary for all its effects? J Pharm Pharmacol 55: 1687–1694

Williamson EM (2001) Synergy and other interactions in

phytomedicines Phytomedicine 8: 401–409

Wolf SA, Bick-Sander A, Fabel K, Leal-Galicia P, Tauber S,

Ramirez-Rodriguez G et al (2010) Cannabinoid receptor CB1

mediates baseline and activity-induced survival of new neurons in

adult hippocampal neurogenesis Cell Commun Signal 8: 12

Xiong W, Cheng K, Cui T, Godlewski G, Rice KC, Xu Y et al.

(2011) Cannabinoid potentiation of glycine receptors contributes

to cannabis-induced analgesia Nat Chem Biol 7: 296–303

Zijicek J, Fox P, Sanders H, Wright D, Vickery J, Nunn A et al.

(2003) Cannabinoids for treatment of spasticity and other

symptoms related to multiple sclerosis (CAMS study): multicentre

randomised placebo-controlled trial Lancet 362: 1517–1526

Zuardi AW (2008) Cannabidiol: from an inactive cannabinoid to adrug with wide spectrum of action Rev Bras Psiquiatr 30: 271–280

Zuardi AW, Finkelfarb E, Bueno OF, Musty RE, Karniol IG (1981).Characteristics of the stimulus produced by the mixture ofcannabidiol with delta 9-tetrahydrocannabinol Arch IntPharmacodyn Ther 249: 137–146

Supporting information

Additional Supporting Information may be found in theonline version of this article at the publisher’s web-site:http://dx.doi.org/10.1111/bph.12944

Appendix S1 PRISMA 2009 Checklist and extendedmethods section for meta-analysis

Appendix S2The CBD data extraction table, followed bysubgroup meta-regression tests

Appendix S3The THCV data extraction table, followed bysubgroup meta-regression tests

Trang 34

computer modelling to

biological effects

Shirin Kahremany1, Ariela Livne2, Arie Gruzman1, Hanoch Senderowitz1

and Shlomo Sasson2

1Division of Medicinal Chemistry, Department of Chemistry, Faculty of Exact Sciences, Bar-Ilan

University, Ramat-Gan, Israel, and2Department of Pharmacology, Institute for Drug Research,

School of Pharmacy, Faculty of Medicine, The Hebrew University of Jerusalem, Jerusalem, Israel

Correspondence

Professor Shlomo Sasson,Department of Pharmacology,Institute for Drug Research,School of Pharmacy, Faculty ofMedicine, The Hebrew University

of Jerusalem, Faculty ofMedicine, Jerusalem 91120,Israel E-mail:

shlomo.sasson@mail.huji.ac.il;Professor Hanoch Senderowitz,Division of Medicinal Chemistry,Department of Chemistry,Faculty of Exact Sciences, Bar-IlanUniversity, Ramat-Gan 52900,Israel E-mail:

dimers interact with other co-activator proteins and form active complexes that bind to PPAR response elements and promotetranscription of genes involved in lipid metabolism It appears that various natural fatty acids and their metabolites serve as

ligand binding domain (LBD) of the receptor Here, we introduce an original computational prediction model for ligand

calculating binding probabilities of 82 different natural and synthetic compounds from the literature These compounds were

accuracy of between 70% and 93% (depending on ligand type) This new computational tool could therefore be used in thesearch for natural and synthetic agonists of the receptor

Abbreviations

ALPHA, amplified luminescent proximity homogeneous assay; CARLA, co-activator-dependent receptor ligand assay;DBD, DNA binding domain; LBD, ligand binding domain; LIC, ligand-induced complex formation assay; MUFA,monounsaturated fatty acids; NTD, N-terminal domain; PPRE, PPAR response elements; PUFA, polyunsaturated fattyacids; RMSD, root mean squared deviation; RXR (also known as NR2B receptors), retinoid X receptor; SFA, saturatedfatty acids; SP, scintillation proximity competition assay; TR-FRET, time resolved-fluorescence resonance energy transfer

Trang 35

The PPAR family

PPARs are ligand-activated transcription factors of the nuclear

hormone receptor superfamily Peroxisome proliferation in

rat liver treated with the anti-hyperlipidaemic compound

clofibrate was reported over 40 years ago (de Duve, 1969)

Subsequently, several other compounds with similar effects

were identified and were collectively termed peroxisome

pro-liferators Issemann and Green cloned the first member of the

family from rat liver, and in 1990 coined the term

‘peroxi-some proliferator-activated receptor’ (Issemann and Green,

1990) Two other members of the family were identified in

1992 and the group now consists of three major subtypes:

PPARα, PPARδ and PPARγ (Dreyer et al., 1993) These receptors

regulate major metabolic pathways, including carbohydrate

utilization, fatty acid oxidation and lipogenesis (Wagner and

Wagner, 2010) They form heterodimers with members of the

retinoic acid receptor (RXR) family and subsequently interact

in a stereospecific manner with PPAR response elements

(PPRE) in DNA to assemble active transcriptional complexes

(Wahli and Michalik, 2012) PPRE sequences are composed of

double hexameric motifs, separated by a short spacer

sequence and organized in a direct, inverted or everted

manner (Kumar and Thompson, 1999) PPARα is

predomi-nantly expressed in the liver and primarily regulates lipid

metabolism (Pyper et al., 2010) PPARγ is mostly expressed in

adipose tissues and controls adipogenesis and carbohydrate

metabolism (Astapova and Leff, 2012)

Roles of PPARδ in the regulation of glucose

and lipid metabolism

The role of the ubiquitously expressed PPARδ in the

regula-tion of physiological and pathological processes in different

tissues have been intensely investigated (Coll et al., 2009;

Ehrenborg and Krook, 2009; Lee et al., 2009; Wagner and

Wagner, 2010; Wolf, 2010; Ehrenborg and Skogsberg, 2013;

Skerrett et al., 2014) The regulation of lipid and glucose

metabolism is considered a major function of PPARδ (Coll

et al., 2009) For instance, it orchestrates the expression of

genes involved in lipid metabolism in mature adipocytes(Wolf, 2010) Other studies have shown that PPARδ activationimproves the plasma lipid profile in humans and in primates

(Oliver et al., 2001; Wallace et al., 2005; Sprecher et al., 2007; Riserus et al., 2008; Thulin et al., 2008) and significantly

decreases high fat diet-induced obesity in rodents (Tanaka

et al., 2003) In addition, PPARδ-null mice exhibited lower

accumulation of lipids in adipose tissue stores (Peters et al., 2000; Sprecher et al., 2007) The specific PPARδ agonistGW501516 increases blood high-density lipoprotein and

decreases triglyceride levels in rhesus monkeys (Oliver et al., 2001) and preventes obesity in mice (Wang et al., 2003).

Furthermore, PPARδ activation reduces intestinal cholesterol

absorption in mice (van der Veen et al., 2005).

PPARδ also plays an important role in the regulation ofperipheral insulin sensitivity and attenuates symptoms of the

metabolic syndrome (Tanaka et al., 2003; Lee et al., 2006; Riserus et al., 2008) Decreased lipid accumulation in skeletal

muscles following PPARδ activation along with proliferation

of mitochondria and a consistent increase in fatty acids dation in skeletal muscles were also linked to PPARδ-

oxi-dependent amelioration of insulin resistance (Dressel et al.,

2003; Ehrenborg and Skogsberg, 2013) Similar beneficialeffects of PPARδ activation were observed in insulin-resistant

obese rhesus monkeys (Oliver et al., 2001) Others showed

that PPARδ stimulation improved glucose tolerance, loweredpostprandial levels of plasma insulin and glucose, reducedhepatic glucose output by increasing glycolysis and thepentose phosphate shunt and augmented fatty acids synthe-

sis and triglycerides content in the liver (Tanaka et al., 2003; Lee et al., 2006; Chen et al., 2008) Conversely, PPARδ-null

mice were glucose intolerant and exhibited a low metabolic

rate (Lee et al., 2006).

These Tables list key protein targets and ligands in this article which are hyperlinked to corresponding entries in http://

www.guidetopharmacology.org, the common portal for data from the IUPHAR/BPS Guide to PHARMACOLOGY (Pawson et al., 2014) and are permanently archived in the Concise Guide to PHARMACOLOGY 2013/14 (Alexander et al., 2013).

Trang 36

Protective role of PPARδ in the development

of atherosclerosis

Active PPARδ may also prevent or delay the development of

atherosclerosis For example, treatment with the PPARδ

agonist L-165041 resulted in reduced monocyte recruitment

to human endothelial cells by reducing the expression of

vascular cell adhesion molecule-1, the secretion of monocyte

chemotactic protein-1 and of the inflammatory cytokines

IL-6 and IL-8 (Rival et al., 2002; Jiang et al., 2009; Liang et al.,

2010) Furthermore, activation of PPARδ by the selective

ago-nists GW0742 and GW501516 augmented the expression of

antioxidant genes, (e.g superoxide dismutase-1, catalase and

thioredoxin), and attenuated the generation of reactive

oxygen species in vascular endothelial cells (Fan et al., 2008).

Others suggested that activated PPARδ augmented cholesterol

efflux from macrophages in atherosclerotic lesions and

thereby decreased transendothelial migration of leucocyte/

monocytes into the arterial wall (For review see Barish et al.,

2008; Piqueras et al., 2009).

PPAR δ protects against pathophysiological

processes in the nervous system

The findings that PPARδ-deficient mice exhibited abnormal

neurophysiological processes, such as decreased myelination,

augmented inflammatory reactions and low score in memory

tests, suggest a critical role for PPARδ in neuronal

develop-ment and function (Peters et al., 2000) Interestingly, CNS

inflammation has been associated with increased level of

inflammatory markers, astrogliosis andτ

hyperphosphoryla-tion (Barroso et al., 2013) Moreover, it was the lack of PPARδ

function in the brain has been linked to increased

vulnerabil-ity to ischaemic insults because of defective antioxidant

responses (Arsenijevic et al., 2006; Pialat et al., 2007)

Addi-tional data, generated from effects of selective PPARδ agonists

in the brain, suggest that PPARδ activation could protect

against neurodegenerative processes (Polak et al., 2005;

Iwashita et al., 2007; Kalinin et al., 2009; Paterniti et al., 2010;

Yin et al., 2010; Martin et al., 2013).

Roles of PPARδ in embryonic, organ and

tissue development

Attempts to generate PPARδ knockout mouse models were

difficult because of high rates of embryo lethality (Michalik

et al., 2001; Barak et al., 2002) Yet, these models revealed

important roles of PPARδ in blastocyst hatching, embryo

implantation, myelination, lipid metabolism and adiposity

and epidermal cell proliferation (Lim et al., 1999; Peters et al.,

2000; Barak et al., 2002; Huang et al., 2007) Furthermore,

PPARδ seemed also involved in morphological adaptive

dif-ferentiation of various tissues, such as skeletal muscles

(Ehrenborg and Krook, 2009), and the development of

oxi-dative type I fibres (Luquet et al., 2003; Wang et al., 2004).

Recent studies suggest that PPARδ regulates cell growth (Lee

et al., 2009): for instance, it increased the number and size of

intestinal polyps and stimulated proliferation of vascular

smooth muscle cells, pre-adipocytes and epithelial cells

(Jehl-Pietri et al., 2000; Hansen et al., 2001; Zhang et al., 2002;

Gupta et al., 2004; Burdick et al., 2006) Importantly, several

PPARδ synthetic agonists exhibited carcinogenic potential

(Ehrenborg and Skogsberg, 2013)

In conclusion, because PPARδ regulates myriad cell andorgan functions, it has become a desirable target for drugdiscovery Development of selective PPARδ agonists for thetreatment and prevention of symptoms of the metabolic syn-drome attracts attention and is highly sought Similarly,PPARδ-selective agonists with enhanced neuroprotective andanti-atherosclerotic properties are of a great interest Yet thecarcinogenic potential of PPARδ agonists should be fullyinvestigated in order to create selective agonists devoid of thisproperty Therefore, PPARδ structural research, detailed analy-sis of ligand binding to the receptor and its activation on thebasis of comprehensive structure activity relationship analy-sis are required to reach these goals

The structure of PPAR δ

Generally, PPARs are organized in four functional domains:the N-terminal domain (NTD), the DNA binding domain(DBD), which includes two zinc fingers, the hinge domain

and the ligand binding domain (LBD) (Schmidt et al., 1992).

The NTD is the most varied domain among the differentPPARs (Helsen and Claessens, 2014) This domain, which isrelatively short, is believed to mediate ligand-independentactivity by promoting protein–protein interactions withco-activators or co-suppressors and by inducing conforma-tional modifications that allow allosteric interactions

(Zieleniak et al., 2008; Helsen and Claessens, 2014)

Interest-ingly, the NTD has not yet been resolved in the full lengthcrystal structure of PPARδ and its precise regulatory interac-tions remain to be resolved The DBD is the most conserveddomain among the various PPARs Two zinc fingers form thefunctional core structure, where theα-helix in the first zincfinger promotes the recognition of specific sequence in thePPRE in the DNA The second zinc finger mediates the het-rodimerization with RXR (Helsen and Claessens, 2014) Otherareas in the DBD further stabilize the DNA-PPAR complex bydirect interactions with the minor groove of the DNA and/oralternatively by stabilizing the interactions with other

partner in the dimer complex (Hsu et al., 1998; Shaffer and Gewirth, 2002; Roemer et al., 2006) The hinge domain,

which separates the DBD from the LBD in all PPARs, contains

a nuclear localization signal and amino acid side chains

ame-nable to post-translational modifications (Anbalagan et al., 2012; Clinckemalie et al., 2012).

The structure of the LBD is similar among the various

PPAR (Bourguet et al., 1995; Renaud et al., 1995): it consists of

a complex of 13 α-helices and four-stranded β-sheets thatform a cavity, which is markedly larger than similar cavities

in other members of the nuclear receptor superfamily TheY-like shaped LBD in PPARs is composed of 25 amino acids(Figure 1): arm-1 forms a ‘tunnel’ that transverses from thesurface of the protein to its internal part, while arm-2 andarm-3 form a cavity Arm-2 is considerably polar, whereasarm-1 and arm-3 are hydrophobic Over 80% of the aminoacid residues in the binding cavity are highly conservedamong the three PPAR isotypes, including four polar residues

in arm-2, which form critical hydrogen bonds with polarmoieties (predominantly carboxylic acids) of ligands Corre-spondingly, PPAR ligands are usually characterized by thepresence of a polar moiety in a predominantly non-polar

molecule (Zoete et al., 2007) Ligand binding selectivity to the

various PPARs is conferred by subtle modifications in the

Trang 37

structure of their LBD (Batista et al., 2012; Carrieri et al.,

2013) It has been shown that a single amino acid mutation

in the LBD can dramatically change ligand recognition by the

receptor (Xu et al., 1999) The large volume of the binding

cavity allows several binding options (dynamic binding

equi-librium) of the lipophilic domain of ligands in the LBD, as

was documented for the interaction of eicosanoic acid with

the LBD PPARs (Xu et al., 2001) or for ragaglitazar with

PPARα/γ (Ebdrup et al., 2003) Interestingly, arm-1 forms a

very narrow tunnel in PPARδ LBD, which restricts the entry of

compounds with bulky moieties near the polar head This

structure eliminates the binding of various PPARsα/γ ligands

to the PPARδ LBD (Xu et al., 1999) This structure also

explains the relatively small number of known ligands to

PPARδ in comparison with the two other isotypes For

instance, the bulky acidic head group in thiazolidinediones

permits their binding interaction with PPARγ but not with

PPARδ Yet the relatively small phenoxyacetic acid moiety in

the PPARδ agonist GW501516 fits well the narrow entry

tunnel to the LBD (Oliver et al., 2001).

PPARδ activation

The current hypothesis of PPAR activation claims that the

binding of a ligand to the LBD triggers conformational

changes in the entire receptor Such changes that occur in

helix 12 of the LBD enable interactions of co-activator

mol-ecules (e.g steroid receptor co-activator-1) with the receptor

(Kallenberger et al., 2003) These conformational changes

also increase the strength of the binding interaction between

PPARs and their cognate partner RXR to form active dimers

that interact with PPRE in gene promoters (Okuno et al.,

2001) The fact that PPARs have significant constitutive ity in the total absence of ligands and co-activators indicatesthat the classical ligand-dependent activation of PPARs is not

activ-exclusive (Issemann and Green, 1990; Hallenbeck et al.,

1992)

This review focuses on ligand binding selectivity and sequent activity of PPARδ The human PPARδ is made of 441amino acids that are organized in the classical NTD (aa 1–70),DBD (aa 71–145), which includes two zinc fingers (aa 74–94and 111–133), the hinge domain (aa 146–254) and the LBD

sub-(aa 254–441) (Schmidt et al., 1992) The secondary structure

of the protein consists of 10β-strands and 15 α-helices While

a full crystal structure of PPARγ has been recently reported

(Chandra et al., 2008), most structural information on PPARδ

is restricted to analysis of LBD and hinge domain crystals

(Fyffe et al., 2006).

It has been shown that certain saturated, unsaturated and polyunsaturated fatty acids (SFA, MUFA andPUFA) and eicosanoids and prostaglandins activate PPARδ

mono-(Benetti et al., 2011) Recently, we have reported that

4-hydroxynonenal (4-HNE) and 4-hydroxydodecadienal(4-HDDE), the peroxidation products of PUFA, activate PPARδ

in cultured endothelial cells and pancreatic β-cells (Riahi

et al., 2010; Cohen et al., 2011b; 2013) The mechanism by

which these two 4-hydroxyalkenals activate PPARδ is unclear.These chemically reactive aldehydes avidly form covalentbonds with nucleophilic groups of amino acids (i.e histidine,lysine, arginine or cysteine) Yet it has been reported thatsteric hindrance prevents 4-HNE covalent interaction withhistidine residues in the LBD of PPARδ (Coleman et al., 2007)

1997), scintillation proximity competition assay (SP) (Xu

et al., 1999), time resolved-fluorescence resonance energy

transfer (TR-FRET) (Naruhn et al., 2010) and amplified nescent proximity homogeneous assay (ALPHA) (Jin et al.,

lumi-2011)

CARLA reflects molecular consequences of ligand binding

to the receptor and is based on the principle that binding ofligands to a nuclear receptor increases the binding affinity of

a labelled ‘broad spectrum’ co-activator protein [35S]-SRC1 tothe receptor complex Principally, CARLA detects productivephysical interactions between two proteins in the presence of

a ligand and is not aimed at determining the association of

ligands with the LBD per se LIC is based on the observation

that ligand-activated nuclear receptors bind to response ments in DNA as dimers Thus, a gel shift mobility assay isemployed to detect the capacity of PPAR-RXR complexes withpotential ligands to interact with PPRE-containing DNAsequences The SP competition assay uses the changes in lightemission when PPARδ, immobilized on scintillant micro-scopic beads with radiolabelled ligand (e.g [3H]-GW2433),interacts with test compounds TR-FRET analysis is an inte-grated method that includes two fluorescent techniques: first,FRET interaction between two fluorophores, a donor and an

ele-Figure 1

PPARδ crystal structure with the cavity in the ligand binding site

(bkue surface) PDB code: 3GWX

Trang 38

acceptor, which triggers energy transfer from the donor to the

acceptor Second, TRF (time resolved fluorescence) method

takes advantage of the long-lived fluorophores lanthanides,

which enables the elimination of non-specific signals Briefly,

Fluormone™ Pan-PPAR Green (Life Technologies, Carlsbad,

CA, USA) is mixed with test compounds, followed by the

addition of a mixture of the PPARδ-LBD and terbium anti-GST

(glutathione-S-transferase) antibody When the Fluormone

Pan-PPAR Green is bound to the receptor, energy transfer

from the terbium-labelled antibody to the tracer occurs and

resolved as a high TR-FRET ratio Competitive ligand binding

to PPARδ is detected by the test compound’s ability to

dis-place the tracer and a reduced FRET signal The ALPHA

bead-based assay resolves the interactions of a fluorophore donor

with its acceptor The donor bead contains a high

concentra-tion of photosensitizers, which converts ambient oxygen to a

more excited singlet state when excited at 680 nm This bead

is covered with an antibody against PPARδ The acceptor bead

is a chemiluminescer that is covered with the LBD of PPARδ

The binding interaction between the antibody and the LBD

across the two beads results in singlet-induced luminescence

PPARδ ligands interfere with the binding interaction between

the beads and lower the luminescence

Using the CARLA, Krey et al identified eicosatetraynoic

acid, eicosapentanoic acid, linoleic acid, linolenic acid,

8(S)-hydroxyeicosatetraenoic [8(S)HETE] acid and bezafibrate as

high-affinity ligands to the LBD of PPARδ (Krey et al., 1997)

Forman et al (1997) used LIC to compare the binding

inter-actions of ligands with PPARδ LBD with their ability to

trans-activate the PPREX3-TK-LUC vector in transfected cells Of

all compounds tested, the best binding affinities were

reported for carbaprostacyclin (cPGI, a synthetic analogue of

PGI2), followed by iloprost (another PGI2 analogue),

arachi-donic and linoleic acid Interestingly, the transactivation

capacity of these compounds in the cell-based assay was

dif-ferent: arachidonic acid > cPGI > iloprost > linoleic acid

Unlike the results of the above-mentioned CARLA assay,

8(S)-HETE exhibited insignificant binding interaction with

PPARδ LBD in the LIC assay and no activity in the cell-based

assay Also, eicosapentanoic acid, predicted to be an

activa-tor of PPARδ in the CARLA, lacked significant binding

inter-actions with the LBD in the LIC assay, while exhibiting a

marked transactivation capacity in the cell-based assay

Moreover, some compounds that interacted positively in the

activation assay (e.g PGA1, PGA2 or 15d-PGJ2) lacked a

sig-nificant binding interaction with the LBD Xu et al (1999)

also tested some of these putative PPARδ ligands in the SP

assay and ranked them as follows: arachidonic acid>

eicosa-pentanoic acid> linoleic acid > linolenic acid These

find-ings correspond well with some of the results of CARLA and

LIC assays Interestingly, the most potent fatty acid tested in

the SP assay was γ-linoleic acid Other potent ligands were

oleic acid, stearic acid, palmitic acid and palmitoleic acid

Using the TR-FRET assay, Naruhn et al (2010) found that

15-HETE was most potent in inducing the binding of a

co-activator-derived peptide to the PPARδ LBD in vitro,

fol-lowed by arachidonic acid and 15-HpETE Yet 8-HETE,

12-HETE and 12-HpETE had no significant interaction with

the LBD Using the ALPHA screen assay, Jin et al (2011)

confirmed that iloprost was bound to the LBD of PPARδ and

PPARα More studies utilizing other methods report that

some of the above-mentioned compounds and dins could interact with PPARδ (Yu et al., 1995) Coleman

prostaglan-et al (2007) identified several arachidonic and linoleic acid

metabolites (e.g 12/15-HpETE, 15-HETE) as potent tors of PPARδ Riahi et al (2010) and Cohen et al (2011b)introduced 4-hydroxyalkenals as another class of PPARδ acti-vators The peroxidation products of arachidonic acid,4-HDDE and 4-HNE, transactivated PPREX3-TK-LUC intransfected vascular endothelial cells and cultured pancreaticβ-cells

GW0742 and TIPP204 (Sznaidman et al., 2003), and amino

acid side chains in the LBD Hitherto, no crystal structure ofthe whole monomeric PPARδ protein or its heterodimer withRXR has been reported We decided to use the X-ray crystal-lographic data of the above-mentioned complexes with syn-

thetic ligands and create an in silico model that may predict

the degree of possible direct interactions of natural ligands(fatty acids and their metabolites) and other synthetic ligandswith the PPARδ LBD This model also tests the assumptionthat both large (e.g long fatty acid and their metabolites) andsmall (e.g hydroxyalkenals) ligands may enter and interactwithin the bulky cavity in the LBD

Our model was developed based on previously publishedcrystallographic data of 16 PPARδ LBD-ligand complexesand validated on a database of 82 compounds (SFA, MUFA,PUFA and some of their enzymatic and non-enzymaticmetabolites and several synthetic compounds; see Tables 2and 3) These were evaluated for their potential to bind toPPARδ LBD, using pharmacophore modelling and dockingsimulations Because the binding site of the protein con-tains two histidine residues (H323, H449) that are impor-tant for ligand binding, we also examined the effect of theprotonation states of these two residues on the ligandbinding modes The molecular modelling methods used for

the following in silico analysis are given in the Supporting

is in line with a previous study of PPARγ agonists (Iwata et al.,2001) This binding hypothesis was transformed into a phar-macophore model by superposing the 16 crystallographicligands in their complex (i.e bioactive) conformations Theresulting pharmacophore was further refined by adding

Trang 39

Table 1

Activity data for the 16 crystallographic ligands of PPARδ bound to the ligand binding domain

Protein Data Bank code Ligand structure EC 50 (nM) Reference

explore.do?structureId=3d5f

Trang 40

Table 1

Continued

Protein Data Bank code Ligand structure EC 50 (nM) Reference

Ngày đăng: 12/04/2017, 15:24

TỪ KHÓA LIÊN QUAN

TÀI LIỆU CÙNG NGƯỜI DÙNG

  • Đang cập nhật ...

TÀI LIỆU LIÊN QUAN

🧩 Sản phẩm bạn có thể quan tâm