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Upon altering the plasma membrane cholesterol content of these cells, membrane localization and the activity of MRP1 were analyzed.. Therefore, using a detergent-free method to isolate t

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multidrug-resistant lung cancer cells ) modification of

ABCC1 (MRP1) localization and functionality

Carole Marbeuf-Gueye, Ve´rene Stierle, Paiwan Sudwan, Milena Salerno and

Arlette Garnier-Suillerot

Laboratoire Biophysique Mole´culaire, Cellulaire et Tissulaire (BioMoCeTi), UMR CNRS 7033, Universite´ Paris 13 et Paris 6, Bobigny, France

A major obstacle to the success of chemotherapy is

multidrug resistance (MDR) [1] The classical MDR

phenotype is characterized by cross-resistance to a

wide variety of structurally unrelated chemotherapeutic

agents of natural origin after exposure to only one

The roles, in vitro, of ABCB1 (P-glycoprotein, P-gp)

and ABCC1 (multidrug resistance-associated protein,

MRP1) in MDR are uncontested [2–5] Both proteins

are members of the ATP-binding-cassette (ABC)

super-family of transport proteins, which lower the

intracel-lular drug content through active drug efflux

The well-documented membrane protein sensitivity

to a lipid environment has led to the hypothesis of functional cross-talk between membrane proteins and membrane microdomains such as rafts and caveolae, inspiring numerous studies over the past 10 years [6] Both types of microdomain, rich in cholesterol and glycosphingolipids, are supposed to share similar physicochemical properties, in particular a Lo phase, less fluid than a liquid crystal phase [7] Raft domains, and by extension caveolae, are generally isolated from intact cells on the basis of their insolubility in cold,

Keywords

ABCC1 functionality; ABCC1 localization;

membrane cholesterol level; multidrug

resistance; raft

Correspondence

M Salerno, Laboratoire BioMoCeTi, CNRS

UMR 7033, UFR SMBH, 74 rue Marcel

Cachin, 93017 Bobigny, Cedex France

Fax: +33 1 48 38 88 88

Tel: +33 1 48 38 77 48

E-mail: m.salerno@smbh.univ-paris13.fr

(Received 20 November 2006, revised 20

December 2006, accepted 10 January 2007)

doi:10.1111/j.1742-4658.2007.05688.x

The multidrug resistance-associated protein transporter ABCC1 (MRP1) is

an integral plasma membrane protein involved in the multidrug resistance phenotype It actively expels a number of cytotoxic molecules from cells

To gain insight into the modulation of the functional properties of this integral membrane protein by cholesterol, a main component of the lipid bilayer, we used multidrug-resistant GLC4⁄ ADR cells, which overexpress MRP1 Upon altering the plasma membrane cholesterol content of these cells, membrane localization and the activity of MRP1 were analyzed A detergent-free methodology was used to separate ‘light’ and ‘heavy’ plasma membrane fractions Our data show that MRP1 was exclusively found in

‘light’ fractions known as L0phase membrane microdomains, together with

 23% of gangliosides GM1 and 40% of caveolin-1 Depletion of the mem-brane cholesterol level to 40% by treatment with the cholesterol-chelating agent methyl-b-cyclodextrin did not modify MRP1 activity, as evidenced either by the rate of efflux of pirarubicin or that of glutathione Further cholesterol depletion below 40% yielded both a partial shift of MRP1 to the high-density fraction and a decrease of its functionality Taken together, these data suggest that MRP1 funtionality depends on its local-ization in cholesterol-rich membrane microdomains

Abbreviations

ABC, ATP-binding cassette; COase, cholesterol oxidase; CTB, cholera toxin B; GSH, glutathione; GST, glutathione S-transferase; HRP, horseradish peroxidase; MbCD, methyl-b-cyclodextrin; MCB, monochlorobimane; MDR, multidrug resistance; MRP1, multidrug resistance-associated protein; P-gp, p-glycoprotein; PIRA, pirarubicin.

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nonionic detergents such as Triton X-100, Brij 96 or

98, Tween-20 or Chaps octylglucoside In fact, the

widely different sensitivities of membrane proteins to

extraction by various detergents is well documented,

and, barring possible artefacts, suggests that lipid rafts

represent a heterogeneous collection of domains

show-ing differences in both lipid and protein content [8,9]

Other protocols without detergent have also been used,

and present the advantage of not making a

preselec-tion of the microdomain protein or lipidic components

by the detergent [10]

Recent studies of the colocalization of ABC

transport-ers such as P-gp in raft or caveolae microdomains have

been interpreted in different ways [11] Similar studies on

MRP1 are scarce, and have only used methods with the

detergents Lubrol or Triton X-100 [12–15] Hinrichs

et al [12] found that MRP1 was predominantly located

in the Lubrol-based fraction of detergent-insoluble

membrane domains in the colchicine-selected cell line

HT29-col Although there was a cocalization of

caveo-lin-1 and MRP1 in the low-density fraction, they

pro-posed a different localization within the microdomains,

on the basis of immunoprecipitation experiments with

sequential Triton X-100 and Lubrol extraction

The aim of this work was to determine the

localiza-tion of MRP1 in the plasma membrane and to

deter-mine whether the modification of its localization

would modify its functional properties Therefore,

using a detergent-free method to isolate the

low-den-sity microdomains of the MDR lung cancer cell line

GLC4⁄ ADR, we studied the effect of cholesterol

depletion by MbCD (a) on the localization of MRP1

and (b) on the functionality of MRP1, i.e its ability to

pump out an anthracycline derivative, pirarubicin

(PIRA) on the one hand and reduced glutathione

(GSH) on the other hand Our data show that MRP1

is totally localized in the low-density membrane

frac-tion, together with some GM1 and caveolin-1 The

reduction of cholesterol to 40% did not affect the

anthracycline transport by MRP1 However, when

more cholesterol was removed, we observed a shift of

MRP1 from the low-density to the high-density

fraction membrane, paralleled by a decrease of its

functionality

Results

The GLC4 small lung cancer cell line, and its

multi-drug-resistant counterpart GLC4⁄ ADR, were used to

study the influence of cholesterol on the activity of

MRP1 in its membrane microenvironment

The amount of intracellular nonesterified cholesterol

was determined, together with the rate of

MRP1-mediated efflux of the anthracycline derivative, PIRA, and of GSH Fifteen independent experiments were performed on 15 different days During that time, the resistance factor varied slightly, yielding a rate of MRP1-mediated efflux of PIRA, Va, which varied within the range 0.4–0.8· 10)18molÆcell)1Æs)1 Concom-itantly, the amount of cholesterol present exhibited some variation within the range 1.3–2.0· 10)14molÆcell)1 For this reason, the data are presented in term of ratios between the rate of PIRA efflux in the presence

of modulator to that in the absence of modulator; the same holds for the rate of GSH efflux and for the cholesterol concentration In non-MbCD-treated cells,

no correlation was found between the membrane cholesterol content and the MRP1-mediated efflux of PIRA

Effect of MbCD on cellular cholesterol content Cells were incubated with 15 mm MbCD for various times ranging from 30 s to 20 min, and the cholesterol content was determined As can be seen in Fig 1, cellular cholesterol depletion was fast, 50% depletion being observed after less than 1 min, and 80% deple-tion being observed after 10 min of incubadeple-tion; this was not modified by a longer time of incubation

Effect of cholesterol depletion on the rate

of MRP1-mediated efflux of PIRA Cells were incubated for 10 min with various MbCD concentrations, ranging from 0 to 12 mm This incuba-tion yielded an increase in the cell membrane permeab-ility to PIRA In other words, the rate of passive uptake of the drug in the presence of MbCD, VMbCDþ ,

is higher than the rate, V+, in its absence; for instance,

a 1 h incubation of cells with 15 mm MbCD yielded a three-fold increase of the rate of PIRA passive uptake

In order to determine an eventual impact of MbCD on the rate of MRP1-mediated efflux of PIRA, experi-ments were performed with energy-depleted resistant cells, which were incubated with MbCD as previously described At steady state, the incorporation of PIRA was the same as in sensitive cells [16–20] At this stage, the addition of 5 mm glucose yielded an increase in the fluorescent signal due to the MRP1-mediated efflux

of the drug only, and as there was no concentration gradient across the plasma membrane, the effect of MbCD on passive PIRA diffusion did not need to be taken into account (Fig 2)

The cholesterol content of the cells was also deter-mined on the same samples Figure 3 shows the plots

of VMbCD

a ⁄ Va as a function of [Chol]MbCD⁄ [Chol]

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Va and VMbCD

a are the rates of MRP1-mediated efflux

of PIRA before and after treatment with MbCD,

respectively [Chol] and [Chol]MbCD are the cellular

cholesterol contents before and after treatment with

MbCD They are the mean of five independent

experi-ments performed on different days As can be seen,

cholesterol depletion to 40% of the initial content did not give rise to modification of the ratio VMbCD

a ⁄ Va that is characteristic of the MRP1-mediated efflux of PIRA However, further depletion yielded a decrease

of the ratio

Effect of cholesterol depletion on the rate

of MRP1-mediated efflux of GSH

VGSH was determined after incubation of cells with MbCD for 5 min Measurement was also performed after incubation of cells for 30 min with 5 mm MbCD;

in both cases, no modification of the rate of MRP1-mediated efflux of GSH was observed

Effect of Triton derivatives on the MRP1-mediated efflux of PIRA Triton X-45 (n¼ 5) and Triton X-165 (n ¼ 16) were used at nonpermeabilizing concentrations The active efflux was measured: energy-depleted cells were incuba-ted with 1 lm PIRA in the presence of various concen-tration of Triton, either X-45 or X-165 At steady state, glucose was added and the rate, Va, of pump-mediated efflux of drug was measured Figure 4 shows the plot of VT

a⁄ Va as a function of Triton concentra-tion, where VT

a and Va are the rates of efflux in the

Fig 3 Variation of the MRP1-mediated efflux of PIRA as a function

of the fraction of cholesterol present in the cells V MbCD

a ⁄ V a  is plot-ted as a function of [Chol] MbCD ⁄ [Chol] Cholesterol depletion was obtained by 10 min of incubation of cells with different MbCD con-centrations Va and V MbCD

a are the rates of MRP1-mediated efflux

of PIRA, before and after, respectively, treatment with MbCD [Chol] and [Chol] MbCD are the cellular cholesterol contents before and after treatment with MbCD They are the mean ± SE of five independent experiments performed on different days.

Fig 1 Time course of cholesterol depletion in GLC4 ⁄ ADR cells by

incubation with MbCD Cells (10 6 ⁄ mL) were incubated in Hepes

buffer in the presence of 15 m M MbCD for various times, ranging

from 0 to 30 min Data points are from a representative experiment

(n ¼ 3).

Fig 2 Incorporation of PIRA in energy-depleted GLC4 ⁄ ADR cells

and determination of the active efflux rate (Va) Cells, 10 6 ⁄ mL,

were incubated for 15 min with MbCD at concentrations equal to

0 m M (a), 10 m M (b) Cells were then centrifuged as explained

under Experimental procedures, and incubated with 1 l M PIRA.

The fluorescence intensity at 590 nm (kex¼ 480 nm) was recorded

as a function of the time of incubation of cells with PIRA The

act-ive efflux rate (Va) was determined from dF⁄ dt after the addition of

glucose.

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absence and presence of Triton, respectively Fifty per

cent inhibition of PIRA efflux was observed with

16 ± 2 lm Triton, either X-45 or X-165 Similar

experiments were also performed with Triton X-100

(data not shown), and strictly analogous data were

obtained

MRP1, GM1 and caveolin-1 distribution within

membrane fractions

In order to determine the effect of MbCD on the

integrity of rafts and the localization of MRP1, GM1

and caveolin-1, GLC4⁄ ADR cells were treated or not

treated with MbCD Low-density membrane fractions

were then isolated, and the distributions of MRP1,

GM1 and caveolin-1 were assessed by western blotting

and dot blotting of the analytical density gradients

(Figs 5 and 6) Fraction 1 represents the top of the

gradient, and fraction 11 is the bottom of the gradient

Fractions 3 and 4 and fractions 6 and 7 contain the

10%⁄ 22% and 22% ⁄ 35% sucrose interface,

respect-ively In untreated cells, 100% of MRP1 was found in

fraction 4, 40% of GM1 was found in fraction 4 and

 10–15% in fractions 5–9, fractions 8 and 9

corres-ponding to the cytoplasm and intracellular membranes,

and caveolin-1 was present in all the fractions but was

slightly more abundant in fraction 4 than in the others

After mild treatment with MbCD, the amount of

MRP1 present in fraction 4 decreased to 70%, with a

shift of 30% to fraction 6; GM1 present in fractions 4

decreased to 25%, whereas in fraction 6 it increased

to 20%, and it remained equal to 15% in fractions

6–9 The amount of caveolin-1 present in fraction 4 also decreased slightly

Discussion

Membrane lipids do not form a homogeneous phase consisting of glycerophospholipids and cholesterol, but

a mosaic of domains with unique biochemical composi-tions Among these domains, those containing sphingol-ipids and cholesterol, referred to as lipid rafts, have received much attention in the past few years [21] Tight interactions between the sterol and the sphingolipids result in the formation of domains that are resistant to solubilization in detergents at low temperature [22–24] and are destabilized by cholesterol-depleting and sphingolipid-depleting agents Caveolae can be consid-ered as a functional specialized raft, because they con-tain several specific lipids and proteins typical of

Fig 4 Effect of Triton on MRP1-mediated efflux of PIRA VT⁄ V a  is

plotted as function of the Triton X-45 (d) or Triton X-165 (h)

added to the cells V T and Va are the rates of MRP1-mediated

efflux of PIRA in the presence or in the absence, respectively, of

Triton.

B

C

A

β

Fig 5 Detection of MRP1 in GLC4 ⁄ ADR cell lysates GLC4 ⁄ ADR cells were lysed by sonication, before (empty square) or after (full circle) treatment with MbCD The lysate was separated by density centrifugation, and collected from the top in 1 mL fractions Frac-tion 1 is from the top of the gradient (A) MRP1 expression was analyzed with IMAGE J v1.30 software In the absence of treatment with MbCD, fraction 4 contains MRP1 (100%) After treatment with MbCD, MRP1 is found in fraction 4 (70%) and in fraction 6 (30%) Immunodetection of MRP1 in the absence (B) and in the presence (C) of treatment with MbCD S and R stand for GLC4 (sensitive) and GLC4 ⁄ ADR (resistant) cells.

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detergent-resistant-membrane components They are

typical flask-shaped invaginations of the plasma

mem-brane that originate from the presence of caveolin

fam-ily proteins Among the three isoforms, caveolin-1,

caveolin-2 and caveolin-3, caveolin-1 is the predominant

isoform responsible for this structure and is used as a

biochemical marker of caveolae [25,26] It now seems

clear that caveolae are stable membrane domains that

are kept in place by the actin cytoskeleton Rather than

having a specific function, caveolae might be considered

to be multifunctional organelles with a physiologic role

that varies according to cell type and cellular needs

[25,26] Importantly, the various possible functions of

caveolae do not seem to be of vital importance for the

organism, as reflected by the relatively weak phenotype seen in the knockout mice

Caveolae have recently been shown to be involved

in MDR However, reports on the effect of caveolins

on the development of MDR are controversial: Caveo-lin-1 expression has been shown to be upregulated in MDR phenotypes in a number of human cell lines [27,28], but expression of caveolin-1 and caveolin-2 has not been detected in several MDR cell lines that express high levels of P-gp [29–31], suggesting that caveolin-1 expression is not associated with that of P-gp protein or MDR1 genes [32] Increased levels of glucosylceramide have been observed in many MDR tumor cells [33–35]

These conflicting data can be explained by the use

of different methods to isolate rafts and⁄ or caveolae Actually, most biochemical purifications of lipid rafts are based on an operational definition, namely that they are insoluble in Triton X-100 and have low buoy-ant density A simplified definition of rafts is the 1% Triton X-100-insoluble material that floats at the inter-face of a 5%⁄ 30% sucrose step gradient [36] Thus, Triton X-100-resistant lipid rafts are distinguished from bulk plasma membrane because they are enriched

in cholesterol and sphingolipids, but are relatively depleted in glycerolphospholipids Subsequent to the identification of low-density detergent-resistant domains in Triton X-100 cell extracts, a variety of other detergents, including Lubrol WX, Lubrol PX, Brij 58, Brij 96, Brij 98, Nonidet P40, Chaps, and octylglucoside, have been employed at different con-centrations to prepare detergent-resistant membrane domains [37–41] Unsurprisingly, use of these different detergents in the preparation of rafts yielded mem-brane domains with different lipid compositions from those of standard, Triton X-100-resistant membranes [42] It is not clear whether this heterogeneity pre-existed in rafts or was induced by the application of the detergent

However, nondetergent methods that do not involve the solubilization properties of membranes can be used

to isolate rafts These methods largely obviate prob-lems such as membrane mixing and the selective extraction of lipids In addition, these preparations seem to retain a greater fraction of inner-leaflet-membrane lipids [43] than detergent-extracted rafts do, and may therefore yield domains in which the coupling between raft leaflets is maintained [44,45] For these reasons, rafts prepared by nondetergent methods seem more likely to reproduce the in vivo composition of these microdomains accurately

Several studies have been performed to determine whether P-gp is localized with raft or caveolae;

A

B

Fig 6 Detection of GM1 and caveolin-1 in GLC4 ⁄ ADR cell lysates.

GLC4 ⁄ ADR cells were lysed by sonication, before (empty square)

or after (full circles) treatment with MbCD The lysate was

separ-ated by density centrifugation, and collected from the top in 1 mL

fractions Fraction 1 is from the top of the gradient (A) GM1

con-tent and (B) caveolin-1 expression were analyzed with IMAGE J v1.30

software.

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however, very few studies have been done with MRP1

[12–14] In this work, after cholesterol extraction from

the membrane, we measured both the functionality of

MRP1 and its localization in the plasma membrane

We report that membrane cholesterol is a central

ele-ment in the control of both MRP1 functionality and

localization in the GLC4⁄ ADR cell line

In this study we used a nondetergent method to

iso-late rafts In this isolation procedure, the light and

heavy fractions were found to be derived from the

plasma membrane, whereas the extra-heavy third

frac-tion originated mainly from intracellular components

We examined the distribution of signaling molecules as

well as plasma membrane markers in each fraction

Our data show that MRP1 is exclusively localized in

light membrane fraction 4 (Fig 5) Hinrichs et al also

found, with the detergent-based method, that MRP1

was localized in microdomains in human colon

carci-noma cells (HT29col) Nevertheless, MRP1 localization

in microdomains was partial [12]

Caveolin-1, the marker of caveolin, and GM1, the

marker of rafts, are also found in microdomain

frac-tion 4 It should be emphazised that it is difficult to

distinguish between caveolar and noncaveolar rafts,

given the cofractionation properties that they have in

common Caveolin-1 is present not only in light

frac-tion 4, but in all the membrane cell fracfrac-tions (Fig 6)

This is not surprising, as it is now clear that multiple

locations for caveolin-1 exist throughout the cell, and

caveolin-1 has been reported to be present in the

plasma membrane and in a number of other cellular

sites, including mitochondria, the endoplasmic

reticu-lum reticu-lumen, and secretory vesicles [26] GM1

distribu-tion was similar to that of caveolin-1 in ‘light’ and

‘heavy’ membranes

In a first set of experiments, in order to determine

whether cholesterol affects MRP1 function, we used

MbCD to extract cholesterol from the lipid phase of

intact living cells MbCD is a highly hydrophilic cyclic

oligosaccharide that specifically binds sterol, rather

than other membrane lipids, to form water-soluble

complexes [45], without causing further membrane

per-turbation by insertion [46] Depletion of the membrane

cholesterol level down to 40% by treatment with the

cholesterol-chelating agent MbCD did not modify

MRP1 activity, as followed either by the rate of efflux

of PIRA or that of GSH However, further cholesterol

depletion below 40% yields both a partial shift of

MRP1 to the high-density fraction and a decrease of

its functionality (Figs 3 and 5) Indeed, membrane

models made of binary or ternary cholesterol lipid

mixtures can exhibit a bell-shaped phase diagram

where the cholesterol-rich L0 phase coexists with the

LCphase [47,48] For these reasons, it is not surprising that MRP1 funtionality is not affected by cholesterol depletion down to 40%, as the microdomains are probably still present

At this stage, it is interesting to compare the present data with those that we have previously obtained with K562⁄ ADR cells overexpressing P-gp The transport functionality vs the cholesterol content, obtained after different MbCD treatments, shows different profiles for P-gp and MRP1 (Fig 3 and [49]) In K562⁄ ADR cells, which do not express caveolin-1 protein and therefore do not possess caveolae, the progressive removal of cholesterol with MbCD yields a progressive inhibition of P-gp functionality, whereas MRP1 func-tionality does not depend on the cholesterol content being reduced to 40% Given that in K562⁄ ADR cells, P-gp is not localized in the microdomain, whereas we found that MRP1 is exclusively localized in the micro-domain, these different profiles could be explained by the fact that cholesterol could be more easily removed from nonmicrodomain regions than from the LO phase

in the microdomain, where it is more tightly packed Now let us compare the impact of the membrane fluidity on P-gp and MRP1 transport activity We have checked (a) that the passive influx of PIRA was the same in both sensitive and energy-depleted cells, mean-ing that there is no variation of passive influx durmean-ing the acquisition of MDR in the two cell lines [20], and (b) that the initial rate of passive PIRA uptake was not modified by the addition of fluidizing agents such

as Triton derivatives at the low concentrations used in this study [50] The effect of Triton derivatives on P-gp and MRP1 functionality was measured in K562⁄ ADR and GLC4⁄ ADR cells, respectively, It appears that

6 ± 2 lm Triton X-45 yields 50% of P-gp function-ality inhibition [50], whereas a concentration of

16 ± 2 lm was required to inhibit 50% of MRP1 functionality, corroborating the observation that as MRP1 is localized in a more tightly packed fraction than P-gp, more Triton is required to modify the fluid-ity of the membrane around the transporter Second, the whole membrane fluidity of these two cell lines can

be compared using the rate of passive influx of various molecules through the plasma membrane We have previously measured the rate of passive influx of anthracycline derivatives in these two cell lines [20], and we have observed that, systematically, for a given molecule the rate of its influx in GLC4⁄ ADR cells was 3–4 times higher than in K562⁄ ADR cells, showing that, as a whole, the GLC4⁄ ADR membrane is more fluid than the K562⁄ ADR membrane

In summary, our results show that MRP1 is localized in microdomains and that its functionality,

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measured as its ability to pump out PIRA, is

con-served when it is localized in rafts only In addition,

cholesterol perturbation is more difficult to achieve in

rafts than in the other membrane regions Altogether,

these data suggest that MRP1-related functions can be

regulated by the microdomain membrane

Experimental procedures

Cell lines and culture

GLC4 cells and MRP1-overexpressing GLC4⁄ ADR cells

[51] were cultured in RPMI 1640 (Sigma Chemical Co., St

Louis, MO) medium supplemented with 10% fetal bovine

serum (Gibco Cergy Pointoise, France) at 37C in a

humidified incubator with 5% CO2 The resistant

GLC4⁄ ADR cells were cultured with 1.2 lm doxorubicin

until 1–4 weeks before the experiments Cell cultures used

for experiments were split 1 : 2 1 day before use in order to

ensure logarithmic growth Cells (106⁄ mL; 2 mL per

cu-vette) were energy-depleted by preincubation for 30 min in

Hepes buffer with sodium azide but without glucose [52]

We have previously checked that no P-gp was expressed in

the resistant cells and that anthracycline efflux is due only

to MRP1 [52]

Drugs and chemicals

Doxorubicin and PIRA were kindly provided by

Pharma-cia-Upjohn (St Quentin Yualines, France) Concentrations

were determined by diluting working solutions to

approxi-mately 10)5mwith e480¼ 11 500 m)1Æcm)1 Working

solu-tions were prepared just before use MbCD (mean degree

of substitution: 10.5–14.7), horseradish peroxidase (HRP),

GSH, dithiothreitol and compounds of the polyoxyethylene

series were purchased from Sigma and were dissolved in

water Trade names of polyoxyethylene (where n is the

number of ethylene oxide units) are as follows: Triton X-45

(n¼ 5), Triton X-100 (n ¼ 9.6) and Triton X-165 (n ¼

165) 10-Acetyl-3,7-dihydroxyphenoxazine (Amplex Red)

and monochlorobimane (MCB) were supplied by Molecular

Probes (Eugene, OR) Before the experiments, the cells were

counted, centrifuged at 5000 g for 30 s and resuspended in

Hepes buffer solutions containing 20 mm Hepes plus

132 mm NaCl, 3.5 mm KCl, 1 mm CaCl2 and 0.5 mm

MgCl2 at pH 7.3, with or without 5 mm glucose Other

chemicals were of the highest grade available Deionized

double-distilled water was used throughout the experiments

MRPm5 anti-MRP1 mouse serum was purchased from

Alexis Biochemical (San Diego, CA, USA), anti-caveolin-1

(N-20 sc 894) rabbit serum was supplied by Santa Cruz

Biotechnology (Santa Cruz, CA, USA) Poly(vinylidene

difluoride) membrane was purchased from Hybond-P,

Amersham Pharmacia Biotech (Orsay, France)

Determination of the nonesterified cholesterol content of GLC4 cells

The nonesterified cholesterol assay was adapted from a spectrofluorometric method used in the kit assay from Molecular Probes [53] Briefly, cells, 2.5· 106mL)1, were washed once with NaCl⁄ Piand suspended in 1 mL of reac-tion buffer The reacreac-tion buffer at pH 7.4 contained 0.1 m NaCl⁄ Pi, 0.05 m NaCl, and 0.1% Triton X-100 Samples were incubated at 37C for 15 min, and this was followed

by sonication on ice (three times for 30 s) and then one additional hour of incubation at 37C under continuous stirring Unless indicated otherwise, 160 lL of this sample was added to the reaction buffer (total volume 1.6 mL), and the fluorescence signal at 560 nm (kex¼ 585 nm) was monitored continuously when the following reactants were added: 50 lm Amplex Red, 0.5 UÆmL)1 HRP, and 0.1 UÆmL)1cholesterol oxidase (COase) The concentration

of cholesterol in the solution was proportional to the differ-ence of the fluorescdiffer-ence signal DF¼ FCOase) FHRP, where

FHRP and FCOase are the fluorescence signal intensities before and after the addition of HRP and COase, respect-ively Because the interaction of the cell suspension with HRP yielded a small change in the fluorescence signal (not shown), a control standard was systematically carried out

in the presence of 160 lL of sonicated cell suspension to which 0–10 lm cholesterol solution was added The curve

DF¼ FCOase) FHRPagainst the exogenous cholesterol con-centration was linear within the 0–5 lm range Cholesterol titration was not affected by the presence of MbCD at the concentrations used in this study

Treatment of cells with MbCD The methylated derivatives of b-cylodextrin are known to preferentially trap membrane cholesterol in comparison to other cyclodextrins, which also show affinity for phospho-lipids and proteins [45] We therefore used a methylated b-cylodextrin (MbCD) with a substitution degree of 10.5– 14.7 to study the effect of cholesterol depletion on GLC4⁄ ADR and GLC4 cells Cells were grown as des-cribed The standard culture medium was replaced with He-pes buffer, to which 2–20 mm MbCD had been added Unless stated otherwise, cells were then incubated for

10 min at 37C Because MbCD interacted with anthra-cycline and modified the fluorescence signal, cells were washed with Hepes buffer, and the transport activity was then measured as described below

Cellular anthracycline accumulation The rationale and validation of our experimental set-up for measuring the kinetics of the transport of anthracyclines in tumor cells has been extensively described and discussed

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before [16–19] It is based on the continuous

spectrofluoro-metric monitoring (Perkin Elmer LS50B spectrofluorometer

Perkin Elmer, Courtabouef, France) of the decrease in the

fluorescence signal of anthracycline at 590 nm (kex¼

480 nm) after incubation with the cells in a 1 cm quartz

cuvette (Fig 2) The decrease in fluorescence occurring

during incubation with cells is due to the quenching of

fluorescence after intercalation of anthracycline between the

base pairs of DNA We have previously shown that this

methodology allows the accurate measurement of the free

cytosolic concentration of anthracyclines under steady-state

conditions, their initial rates of uptake, and the kinetics of

active efflux [16–20]

Determination of the MRP1-mediated efflux

of PIRA

Cells (1· 106⁄ mL; 2 mL per cuvette) were preincubated for

30 min in Hepes buffer with sodium azide, but without

glu-cose (energy-deprived cells) Depletion of ATP in these cells

was 90%, as checked with the luciferin–luciferase test [54]

The cells remained viable throughout the experiment, as

checked with Trypan blue and calcein vital stain (not shown)

After addition of PIRA, the decrease in the signal was

monit-ored until steady state was reached As the pH of the medium

was chosen to equal the intracellular pH, at steady state, the

extracellular free drug concentration (Ce) was equal to the

cy-tosolic free drug concentration (Ci) Glucose was then added,

which led to the restoration of control ATP levels within

2 min and to an increase in the fluorescence signal due to the

efflux of PIRA ATP-dependent PIRA efflux was determined

from the slope of the tangent of the curve F¼ f(t), where F is

the fluorescence intensity at the time of addition of glucose

(Fig 2) As under these conditions, at the moment of

addi-tion of glucose Ci¼ Ce, the passive influx and efflux were

equal, the net initial efflux represents the MRP1-mediated

active efflux only [52]

GSH measurements

In order to quantify free GSH, either inside the cells or

released in the extracellular medium, an enzymatic essay

was used [55] MCB, itself nonfluorescent, is conjugated to

GSH by glutathione S-transferase (GST) to yield a

fluores-cent adduct [56] We have used this property to develop a

very rapid and sensitive fluorometric method for GSH

measurement [55] Briefly, a 10 mm stock solution of MCB

was prepared in ethanol, and aliquots were stored at

) 80 C in the dark The nonenzymatic reaction that

occurred between GSH and MCB was very slow However,

when GST was added, the increase of the fluorescent signal

characteristic of MCB–GSH derivative formation was very

fast The initial rate of MCB–GSH formation was

deter-mined as the increase in the fluorescent signal between 100

and 150 s after the addition of GST to MCB plus GSH

The MCB and GST concentrations were kept constant at

100 lm and 0.5 UÆmL)1, respectively The fluorescence sig-nal recorded over a short time (50 s), which was used as a measure of the initial rate of MCB–GSH formation, is directly proportional to the concentration of GSH at least within the range 0–20 lm (this corresponded to the concen-trations expected when 106cells⁄ mL were lysed, the intra-cellular GSH concentrations being within the 0–20 mm range) We have checked that oxidized glutathione did not give rise to any modification of the fluorescence signal For the intracellular GSH determination, cells (2· 106

) suspended in 2 mL of buffer were disrupted by sonication

on ice (3· 10 s, power 2) The rate of MCB–GSH forma-tion was followed after addiforma-tion of MCB 100 lm and GST 0.5 UÆmL)1, as described above

For the determination of GSH released by the cells, they were resuspended in Hepes buffer (106⁄ mL) in the absence

or in the presence of the appropriate concentration of MbCD After specified time intervals, 2 mL aliquots con-taining 2· 106cells were centrifuged at 5000 g for 30 s and washed twice, and the GSH in the extracellular medium, and therefore released from the cells, and the GSH present

in the pellet were determined The extracellular concentra-tion of GSH was not affected by 250 lm acivicin, indicating negligible activity of c-glutamyltransferase in the membrane

of GLC4⁄ ADR cells

Isolation of ‘light’ and ‘heavy’ membrane fractions

We used a detergent-free procedure for purification of membrane domains ‘Light’ and ‘heavy’ fractions were iso-lated according to previous methods [10,45,57], with the following modifications GLC4⁄ ADR cells, 10–15 · 106

, were washed twice with NaCl⁄ Piand suspended in this buf-fer (2· 108cells⁄ mL) They were then incubated for 2 h in the absence or presence of 2.5 mm MbCD at 37C with stirring Cells were then again washed twice with NaCl⁄ Pi The pellet was suspended in 500 lL of sodium carbonate buffer at pH 9–10, and sonicated in a cold bath three times

30 s (50 Hz, 117 V, and 80 W) (Vibra cell; Sonics & Mate-rials Inc., Danbury, CT) The lysate was mixed with 80% sucrose to yield 2 mL of 40% sucrose solution This mix-ture was transferred to the bottom of the ultracentrifuga-tion tube (Beckman Instruments, Palo Alto, CA) and was overlaid with 3 mL of 35% sucrose, 3 mL of 22% sucrose, and 3 mL of 10% sucrose solution The ultracentrifugation was performed at 160 000 g for 14 h at 4C with an SW41 swinging rotor Light-scattering bands confined at the 10–22% sucrose and 22–35% sucrose interfaces, respect-ively, were observed Eleven 1 mL fractions were collected

by suction with a syringe from the top to the bottom The velocity of aspiration was kept low in order to avoid distur-bance of the sucrose layers The first fraction was called F1, and the last fraction was called F11 The total protein

Trang 9

concentration was measured in each fraction using the

Bradford reagent (Bio-Rad, Mames La Coquette, France)

Western blotting measurement of MRP1

and caveolin-1 expression

Equal volumes (12 lL) of membrane fractions were mixed

with concentrated SDS reducing buffer (final concentrations

are 0.75% SDS, 45 mm Tris, pH 6.8, 75 mm dithiothreitol)

The samples were then incubated for 1 h at 50C for

MRP1 detection, or for 5 min at 95C for caveolin-1

detection Protein samples were separated on 7.5% (MRP1)

or 12% (caveolin) SDS⁄ PAGE, and then transferred to

poly(vinylidene difluoride) membrane for 2 h and 20 min

for MRP1 in transfer buffer (25 mm Tris-base, 192 mm

gly-cine, 0.1% SDS) and for 1 h and 45 min for caveolin-1 in

transfer buffer (25 mm Tris-base, 192 mm glycine, 0.1%

SDS, 10% methanol) The membrane was blocked with 5%

nonfat dry milk in 0.1% Tween⁄ NaCl ⁄ Piovernight at 4C

and treated with 1 lgÆmL)1 MRPm5 anti-MRP1 mouse

serum (Alexis Biochemical) overnight at 4C, or with

1 lgÆmL)1 anti-caveolin-1 (N-20 sc 894) rabbit serum

(Santa Cruz) for 2 h at room temperature Detection by

HRP-linked was performed according to the manufacturer’s

protocol (ECL plus kit with mouse IgG, HRP-linked whole

antibody; Amersham Pharmacia Biotech) MRP1 and

cave-olin expression were evaluated after densitometric scanning

of film and analysis with image j 1.30 software

Localization of GM1 ganglioside

GM1 is commonly found in high concentrations in rafts

[57], and can be labeled using fluorescein

isothiocyanate-conjugated cholera toxin B (CTB) CTB [45] binds to the

glycosphingolipid GM1, and we used it as a marker for raft

localization in ‘light’ and ‘heavy’ plasma membrane

frac-tions We employed a CTB–HRP conjugate for simple,

rapid detection of ganglioside GM1 Briefly, after activation

of a PVDF membrane with methanol and washing with

water and 0.1% Tween⁄ NaCl ⁄ Pi, 4 lL of each gradient

was dotted onto the wet membrane The air-dried

mem-brane was reactivated and blocked with 5% nonfat dry

milk in 0.1% Tween⁄ NaCl ⁄ Pi After being washed with

NaCl⁄ Pi, the membrane was incubated with

HRP-conju-gated CTB (dilution 1 : 5000, Sigma) in 0.1% Tween⁄

NaCl⁄ Pi for 90 min, rinsed several times with NaCl⁄ Pi,

and then detected by enhanced chemiluminescence

(Amer-sham Pharmacia Biotech) and analyzed with image j 1.30

software

Acknowledgements

We thank Professor Laurence Le Moyec and

Dr Catherine Herve´ du Penhoat for critical review

of the manuscript This work was supported by grants from the Centre National de la Recherche Scientifique and l’Universite Paris XIII

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