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Tiêu đề Mitochondrial targeting of intact CYP2B1 and CYP2E1 and N-terminal truncated CYP1A1 proteins in Saccharomyces cerevisiae: role of protein kinase A in the mitochondrial targeting of CYP2E1
Tác giả Naresh B. V. Sepuri, Sanjay Yadav, Hindupur K. Anandatheerthavarada, Narayan G. Avadhani
Trường học University of Pennsylvania, School of Veterinary Medicine
Chuyên ngành Animal biology
Thể loại Journal article
Năm xuất bản 2007
Thành phố Philadelphia
Định dạng
Số trang 16
Dung lượng 908,12 KB

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Mitochondrial localization of N-terminal truncated CYP1A1 The analysis of the microsomal fractions from yeast strains expressing full-length CYP1A1, + 5⁄ 1A1 and + 331A1 showed significan

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N-terminal truncated CYP1A1 proteins in Saccharomyces

targeting of CYP2E1

Naresh B V Sepuri, Sanjay Yadav, Hindupur K Anandatheerthavarada and Narayan G Avadhani Department of Animal Biology, School of Veterinary Medicine, University of Pennsylvania, Philadelphia, PA, USA

Cytochrome P450s (CYPs) belong to a superfamily of

heme-thiolate enzymes that catalyze the oxidation of

xenobiotic as well as endogenous compounds [1–3] A

majority of the constitutively expressed and inducible

CYPs belonging to families 1–4 are primarily localized

in the endoplasmic reticulum (ER), hereafter referred to

as microsomes However, there is increasing evidence

suggesting that some of the inducible CYPs are also bimodally targeted to the mitochondrial compartment [4–7] Studies from our laboratory and others demon-strated that b-naphthoflavone-inducible CYP1A1, pyrazole-inducible CYP2E1, and phenobarbital-induci-ble CYP2B1, known to be bona fide microsomal forms, are also targeted to mitochondria [5,6,8–10] These

Keywords

chimeric targeting signals; CYP2E1;

evolutionary conservations; mitochondrial

protein targeting; xenobiotic metabolism

Correspondence

N G Avadhani, Department of Animal

Biology, School of Veterinary Medicine,

University of Pennsylvania, 3800 Spruce

Street, Philadelphia, PA 19104, USA

Fax: +1 215 573 6651

Tel: +1 215 898 8819

E-mail: narayan@vet.upenn.edu

(Received 30 April 2007, revised 6 July

2007, accepted 13 July 2007)

doi:10.1111/j.1742-4658.2007.05990.x

Previously we showed that intact rat cytochrome P450 2E1, cytochrome P450 2B1 and truncated cytochrome P450 1A1 are targeted to mito-chondria in rat tissues and COS cells However, some reports suggest that truncated cytochrome P450 2E1 is targeted to mitochondria In this study,

we used a heterologous yeast system to ascertain the conservation of targeting mechanisms and the nature of mitochondria-targeted proteins Mitochondrial integrity and purity were established using electron microscopy, and treatment with digitonin and protease Full-length cyto-chrome P450 2E1 and cytocyto-chrome P450 2B1 were targeted both to micro-somes and mitochondria, whereas truncated cytochrome P450 1A1 (+ 5 and + 33⁄ cytochrome P450 1A1) were targeted to mitochondria Inability

to target intact cytochrome P450 1A1 was probably due to lack of solic endoprotease activity in yeast cells Mitochondrial targeting of cyto-chrome P450 2E1 was severely impaired in protein kinase A-deficient cells Similarly, a phosphorylation site mutant cytochrome P450 2E1 (Ser129A) was poorly targeted to the mitochondria, thus confirming the importance

of protein kinase A-mediated protein phosphorylation in mitochondrial targeting Mitochondria-targeted proteins were localized in the matrix compartment peripherally associated with the inner membrane and their ethoxyresorufin O-dealkylation, erythromycin N-demethylase, benzoxyres-orufin O-dealkylation and nitrosodimethylamine N-demethylase activities were fully supported by yeast mitochondrial ferredoxin and ferredoxin reductase

Abbreviations

BROD, benzoxyresorufin O-dealkylation; CCPO, cytochrome c peroxidase; CYP, cytochrome P450; DHFR, dihydrofolate reductase; DMPS, dolichol mannose phosphate synthase; ERND, erythromycin N-demethylase; ER, endoplasmic reticulum; FDX, ferredoxin 1; FDXR, ferredoxin reductase; NDMA, nitrosodimethylamine; NDMA-d, nitrosodimethylamine N-demethylase; PKA, protein kinase A; Put2, D1-pyrroline-5-carboxylate dehydrogenase; TIM, translocase of inner membrane; TOM, translocase of outer membrane.

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studies led us to propose the concept of chimeric

pro-tein-targeting signals that drive the bimodal targeting of

the same primary translation product to more than one

subcellular compartment [10–12]

Protein targeting to the microsomes requires the

co-translational insertion of the newly synthesized protein

into the microsomal membrane, where the N-terminal

hydrophobic signal sequence of the protein interacts

with a signal recognition particle This interaction

sub-sequently results in the association of the translational

complex with the microsomal membrane [13,14] Thus,

the N-terminal hydrophobic sequences of CYPs are

important for their targeting to and retention in the

ER [15–17] Protein translocation into the

mitochon-dria requires a cytosolic chaperone-mediated

associa-tion of precursor protein with peripheral translocase of

outer membrane (TOM) receptors (TOM20, TOM22

and TOM70), which enables the translocation of

proteins through the outer membrane and the inner

membrane channel-forming proteins, TOM40 and

translocase of inner membrane 23 (TIM23) [18–20]

Our studies defined two distinct mechanisms of

acti-vation of cryptic mitochondria-targeting signals at the

N-terminus of mammalian CYP proteins [4,10] We

found that post-translational processing of CYP1A1

at the 4th and 32nd amino acid residues by a cytosolic

endoprotease is critical for the activation of cryptic

mitochondria-targeting signal at the 33–44 positions

of CYP1A1 [4,8,9] This endoprotease was unable to

cleave the N-termini of CYP2E1 and CYP2B1 [6,12]

In the case of CYP2B1 and CYP2E1, uncleaved intact

proteins were targeted to the mitochondria in both

inducer-treated rat liver and transiently transfected

COS cells [6,10] In both of these cases, protein

kinase A (PKA)-mediated phosphorylation at Ser128

or Ser129 [12] was necessary for the activation of a

cryptic mitochondria-targeting signal at positions

21–36 of the protein [6,12] In contrast to our

obser-vations on the targeting of intact CYP2E1 to

mito-chondria, Neve & Ingelman-Sundberg [21] showed

that an N-terminally truncated CYP2E1 was targeted

to mitochondria in transiently transfected hepatoma

cells [22] The nature and specificity of the

endopro-tease and the site of proteolytic cleavage remain

unknown The same investigators were unable to see

any significant intramitochondrial localization of

intact or N-terminal truncated CYP2E1 in yeast cells

[23] The precise nature of CYP proteins targeted to

mitochondria and the conservation of targeting

mech-anism is important for understanding the evolution

and regulation of bimodal targeting Our primary

objective here was to address this important question

using rigorous approaches

Yeast provides an ideal system for the heterologous expression of genes to study both gene function and metabolism The protein translocation machineries of both the mitochondria and microsomes are highly con-served among mammals and yeast [24,25] As protein trafficking has been very well characterized in budding yeast and is thought to involve a similar translocation mechanism as that in mammalian cells, the yeast expression system is well suited for the study of the bimodal targeting mechanism described mostly in tran-siently transfected mammalian cells As targeting of intact CYP2E1 and the requirement for PKA-mediated phosphorylation for mitochondrial targeting are con-tradicted by other studies [22,23,26], we sought cell systems lacking specific PKA subunits to address this important question The availability of PKA gene dele-tion yeast strains provided another advantage for the present study

We show here that mammalian CYPs are targeted efficiently to both the microsomes and mitochondria in yeast cells, depending on the nature of the chimeric signals that they carry In transformed yeast cells, + 33⁄ 1A1 was exclusively localized to the mito-chondria, whereas + 5⁄ 1A1 was localized in both the mitochondria and microsomes Also, we found that full-length CYP2E1 and CYP2B1 were targeted to the mito-chondria as well as microsomes By using PKA-deficient cells, we further show the importance of PKA-mediated phosphorylation in the mitochondrial targeting of CYP2E1 Most importantly, substrate conversion by mitochondria-targeted CYPs was fully supported by yeast mitochondrial ferredoxin (FDX) + ferredoxin reductase (FDXR), homologs of mammalian ferredoxin and ferrodoxin reductase [27,28]

Results

Expression of intact and truncated rat CYPs in Saccharomyces cerevisiae

The levels of expression of various CYP cDNAs were measured by resolving whole cell extracts on SDS⁄ PAGE and western blot analysis using CYP-specific antibodies As shown in Fig 1A,B, the western blot patterns of CYP proteins in cells transformed with plasmids dihydrofolate reductase (DHFR)-1A1, intact CYP1A1, + 5⁄ 1A1, + 33 ⁄ 1A1 and CYP2E1 were con-sistent with their predicted molecular masses Yeast strain BY4741, transformed with plasmid CYP2B1 cDNA, showed extensive degradation of the CYP2B1 protein (Fig 1B) This result was consistent with a pre-vious report showing similar degradation of CYP2B1

in yeast cells [29] Use of the protease-deficient strain

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pepD as suggested by Liao et al [29] yielded more

intact CYP2B1 protein (Fig 1B) Consistent with the

reported size of CYP2E1 protein, cells transformed

with CYP2E1 cDNA plasmid yielded a 52 kDa band

This extract also yielded additional antibody-reactive

bands of about 28–32 kDa, which probably represent

degradation products

Mitochondrial localization of N-terminal

truncated CYP1A1

The analysis of the microsomal fractions from yeast

strains expressing full-length CYP1A1, + 5⁄ 1A1 and

+ 331A1 showed significant levels of full-length

CYP1A1 protein, reduced levels of + 5⁄ 1A1 protein,

and vastly reduced levels of + 33⁄ 1A1 protein

(Fig 2A, first four lanes) We also found nearly

un-detectable full-length CYP1A1 and clearly visible

+ 5⁄ 1A1 and + 33 ⁄ 1A1 in the mitochondrial fraction

(Fig 2A, last four lanes) As expected, full-length

CYP1A1 and + 5⁄ 1A1 from the microsomal

mem-brane fraction were degraded by trypsin treatment

(Fig 2A, first four lanes) This is consistent with the

model suggesting a transmembrane topology of CYPs

with a single N-terminal membrane anchor and most

of the remaining protein exposed to the cytosolic side

[15,17,30,31] The intramitochondrial localization

of CYPs and their topologies were studied using a

combination of treatment with trypsin, treatment with digitonin plus trypsin, and extraction with alkaline

Na2CO3 + 5⁄ 1A1, + 33 ⁄ 1A1, and TIM23, which was used as an internal control, were protected fully against trypsin up to 100 lgÆmL)1, whereas full-length CYP1A1 was completely digested (Fig 2A, last four lanes) These results suggest that full-length CYP1A1

is peripherally associated with the mitochondria We found that both + 5⁄ 1A1 and + 33 ⁄ 1A1 were resistant

to protease digestion even after selective removal of the outer membrane by digitonin treatment (Fig 2B) Under these conditions, TIM23, with a significant pro-portion of its sequence exposed outside the inner mem-brane, facing the intermembrane space, was degraded significantly These results suggested that the imported + 5⁄ 1A1 and + 33 ⁄ 1A1 proteins were localized inside

of the inner membrane Moreover, the imported + 5⁄ 1A1 and + 33 ⁄ 1A1 proteins were extractable with alkaline Na2CO3 as shown in Fig 2C, suggesting that both proteins are localized in the matrix compartment

in a membrane-extrinsic topology

We found that DHFR-1A1 was peripherally associ-ated with the mitochondria and microsomes, as it was vulnerable to very low concentrations of trypsin, sug-gesting that the intracellular distribution of CYPs was not due to random insertion into the microsomal or mitochondrial compartments (Fig 2D) As expected, TIM23 used as an internal control for the mitochon-drial fraction was protected from protease, whereas dolichol phosphate mannose synthase (DMPS) used as internal control for the microsomes was not protected from the externally added trypsin (Fig 2D) In previ-ous studies, we showed that the positively charged amino acids at positions 34 and 39 were important for targeting of + 5⁄ 1A1 and + 33 ⁄ 1A1 proteins to the mitochondrial compartment In keeping with these observations, the results in Fig 2E show that the asso-ciation of a single mutant (R34D) or double mutants (R34D and K39I) of + 331A1 with the mitochondrial membrane was sensitive to protease treatment (Fig 2E) These results suggest that, as in the mamma-lian cell system, the cryptic signal sequence at amino acids 33–44 serves as a mitochondria-targeting signal

in the yeast system

Mitochondrial localization of intact CYP2E1

in yeast cells Because of the existing ambiguity in the literature on the nature and extent of CYP2E1 import into mito-chondria, we first established the relative purity of mitochondrial preparations by biochemical and elec-tron microscopy techniques Figure 3A (top left panel)

+33/1A1+5/1A1DHFR1A1 1A1

35

47

62

81

kDa

2B1/BY4746

2E1 2B1/pep4

Δ'

25 35 47 62 81 kDa

16

25 35 47 62 81 kDa

16

Fig 1 The levels of expression of CYP1A1, CYP2B1 and CYP2E1

proteins in yeast cells Yeast strains BY4741 or PeP4D,

trans-formed with cDNA constructs, were grown to log phase, and cell

lysates were analyzed by SDS ⁄ PAGE and western blotting (A)

Extracts from cells transformed with the indicated CYP1A1

con-structs were probed with antibody to CYP1A1 (B) Extracts from

cells transformed with CYP2B1 (lanes 5 and 6) and CYP2E1

con-struct were probed with either CYP2B1 antibody (left panel, lanes

5 and 6) or CYP2E1 antibody (right-most panel) All transformations

were done in the BY4741 strain, except for the middle panel of (B),

where the protease-deficient strain PeP4D was used In each case,

50 lg of protein was used for immunoblot analysis.

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shows the transmission electron microscopy pattern of a

representative mitochondrial preparation A

representa-tive field shows several well-defined mitochondrial

parti-cles with minor membrane contamination As shown in

the insets, a large majority of mitochondrial

prepara-tions showed intact inner and outer membrane

compo-nents, confirming the structural integrity of mito-chondrial isolates

As shown in Fig 3B, mitochondrial preparations from cells transfected with plasmid pNS61(CYP2E1 cDNA) lacked significant levels of the microsomal marker protein DMPS, and also the cytosolic protein

Trypsin (µg/mL)

Microsomes

1A1

25 50 100

25

A

C

B

TIM23

+33/1A1

TIM23 +5/1A1

TIM23

Digitonin

Mitochondria Mitochondria

1A1 TIM23 +33/1A1

TIM23 +5/1A1 TIM23

Alk insol Alk Sol.

+5/1A1 mito

TIM23ab 1A1ab

+33/1A1 mito

Alk insol Alk Sol.

+

TIM23

Micro Mito.

Trypsin:

DPMS

+

DHFR/1A1

Micro Mito.

+33(R34D)+33(R34D&K39I) +33(R34D) +33(R34D&K39I)

+33/1A1 +33/1A1

– + – + – +33/1A1

TIM23

Fig 2 Mitochondrial targeting of truncated CYP1A1 in yeast cells Mitochondrial and microsomal fractions of yeast cells expressing CYP1A1, + 5 ⁄ 1A1, DHFR-1A1 and + 33 ⁄ 1A1 were separated by SDS ⁄ PAGE and subjected to western blotting Membrane topologies of mitochondria-associated + 5 ⁄ 1A1, + 33 ⁄ 1A1, CYP1A1 (A, B, C), DHFR-1A1 (D) + 33 ⁄ 1A1, + 33 ⁄ 1A1(R34D) and + 331A1(R34D and K39I) (E) were determined by protease treatment of microsomal and mitochondrial isolates before (A, D, E) or after (B) digitonin treatment In (C), digitonin-treated mitochondria were subjected to alkaline Na 2 CO 3 extraction In (A), increasing concentrations of trypsin (0–100 lgÆmL)1) were used, and in (B), (D) and (E), a fixed concentration (50 lgÆmg)1) of trypsin were used Fifty micrograms of protein in each case was subjected to immunoblot analysis Stripped blots were redeveloped with antibodies to marker proteins, TIM23 (mitochondrial marker) or DMPS, a micro-somal marker.

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3-phospho glycerate kinase (3-PGK), but contained

mitochondria-specific TIM23 protein Additionally, both

the ER and mitochondrial fractions showed CYP2E1

antibody crossreactivity, although the latter fraction

showed 60% lower band intensity The preparations

lacked significant levels of oligomycin-insensitive

NADPH cytochrome c reductase, a microsome-specific

marker enzyme (results not shown) Furthermore, the

mitochondrial preparations contained < 90% of total

cellular cytochrome c oxidase activity (results not

shown) The results in Fig 3C show that both FDXR

(matrix protein) and TIM23 (inner membrane) were

resistant to protease treatment However, addition of

trypsin to digitonin-treated fraction reduced the level

of TIM23 but not that of FDXR The antibody to

mouse FDXR used in this study weakly crossreacts

with the yeast homolog Addition of trypsin to

Triton-solubilized samples completely degraded TIM23 and

FDXR Figure 3D represents a full view of an

immu-noblot of mitochondrial and microsomal proteins

developed with a combination of CYP2E1 and TIM23

antibodies It is seen that both microsomal and mito-chondria-associated CYP2E1 consisted of a major antibody-reactive full-length protein and minor faster-migrating bands Furthermore, the mitochondrial frac-tion crossreacted with TIM23 antibody, whereas the microsomal fraction lacked detectable TIM23 These results suggested that the full-length CYP2E1 is tar-geted to mitochondria in yeast cells

Localization of CYP2E1 in the mitochondrial inner membrane–matrix compartment

We used multiple approaches to determine the precise intramitochondrial localization of CYP2E1 in trans-formed yeast cells In the first approach, we assessed the effects of treatment of mitochondria and mitoplasts with trypsin As shown in Fig 4A, we found that mito-chondria-associated P4502E1 was relatively resistant to trypsin treatment, whereas the outer membrane protein TOM20 was completely degraded Additionally, CYP2E1 was resistant to trypsin when the outer

Micro Mito

2E1

TIM23

TIM23

B

D A

C

PGK 2E1 Cyto Micro Mito.

DPMS

Trypsin:

Digitonin:

Tx-100:

TIM23

+ +

+ + +

+

-Adx-red

Fig 3 The nature of mitochondria-associated CYP2E1 in yeast cells (A) Assessment of the integrity of the isolated mitochondria Mitochon-drial isolates were subjected to scanning electron microscopy as described in Experimental procedures (magnification: · 30 000) (B) The rel-ative purity of the isolated mitochondrial, microsomal and cytosolic fractions Mitochondria, microsomes and cytosol were isolated by differential centrifugation as described in Experimental procedures Fifty micrograms of protein from each fraction was subjected to SDS ⁄ PAGE and probed with antibodies specific for microsomes (DMPS), mitochondria (TIM23), and cytosol (3-phosphoglycerokinase), as indicated (C) Isolated mitochondrial fractions were treated with or without digitonin, trypsin or Triton X-100 (Tx-100; 0.2%) and probed with antibodies against human FDXR and TIM23 as indicated (D) A full gel pattern of the microsomal and mitochondrial fractions of cells express-ing full-length P4502E1.

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membrane was stripped by digitonin Under these

treat-ment conditions, inner membrane-associated TIM23,

which is exposed out of the membrane lipid bilayer

towards the intermembrane space, was degraded in a

concentration-dependent manner (Fig 4A) The case

was similar with the intermembrane space protein,

cytochrome c peroxidase (CCPO) By contrast,

D1-pyrr-oline-5-carboxylate dehydrogenase (Put2), a

matrix-localized protein, was protected against protease

treatment even after stripping of the outer membrane

These results suggest that mitochondria-associated

CYP2E1 is localized inside the inner membrane

In the second series of experiments, we treated intact

mitochondria with various concentrations of digitonin

It is known that low concentrations of digitonin (about

0.05%) selectively damage the outer membrane, and

higher concentrations (about 0.1%) damage the inner

membrane In this experiment, we determined the

con-centration of digitonin required to release

mitochon-dria-associated CYP2E1 into the soluble fraction, and

compare it with the amounts needed to release the

outer membrane-specific marker protein porin and the

mitochondrial matrix protein Put2 Figure 4B shows

that significant CYP2E1 release occurred at digitonin concentrations between 0.05% and 0.1% (w⁄ v), at which concentrations Put2 was also released to the sol-uble fraction to a large extent The release of porin started at a much lower concentration of 0.025% These results further support the possibility that mito-chondria-associated CYP2E1 is located inside the innermembrane compartment

In the third approach, we used alkaline Na2CO3 extraction to determine whether mitochondrial CYP2E1

is a membrane-intrinsic or membrane-extrinsic protein The results showed that most part of the microsomal-associated CYP2E1 resisted Na2CO3 extraction, suggesting a transmembrane topology The mitochon-dria-associated CYP2E1, on the other hand, was mostly partitioned in the soluble fraction, indicating a mem-brane-extrinsic topology (Fig 4C) TIM23, a bona fide inner membrane protein partitioned mostly in the

Na2CO3-insoluble fraction, whereas Put2, a bona fide matrix protein, was nearly completely extracted in the soluble phase (Fig 4C) These results suggest that mito-chondrial CYP2E1 is mostly a membrane-extrinsic protein localized in the matrix compartment However,

Trypsin (µg/mL):

A

B

C

-2E1

25 50

CCPO PUT2 TIM23

Mito

Mito

Mitoplast

Mito

Mitoplast

Mito

Mitoplast

Mitoplast

TOM20 Mitoplast

Mito

Pellet

pPut2 Porin

2E1 Digitonin%:

Supernatant

0.01 0.025 0.05 0.1 0.2 0.4 0.01 0.025 0.05 0.1 0.2 0.4

pPut2 Porin 2E1

Micro Mito Mito

2E1 2E1 TIM23 pPut2

Mito

Fig 4 Intramitochondrial localization of CYP2E1 in transformed yeast cells (A) Mitochondria and mitoplasts from cells expressing CYP2E1 were treated with 0–50 lgÆmL)1trypsin as indicated Mitochondria reisolated by banding through a sucrose layer were analyzed by immuno-blotting (50 lg protein each) with antibody to CYP2E1 Put2, TIM23 and CCPO and TOM20 were used as matrix, inner membrane, inter-membrane space and outer inter-membrane markers, respectively (B) Isolated mitochondria were incubated with increasing concentrations of digitonin (0–0.4%; 0–400 lgÆmg)1protein) for 30 min as described in the text The digitonin-insoluble (pellet, left panel) and digitonin-soluble (supernatant, right panel) fractions were separated by centrifugation (14 000 g for 10 min), analyzed by immunoblot, and probed with anti-bodies to porin (outer membrane marker protein), pPut2 (matrix marker protein), and CYP2E1 (C) Mitochondria of yeast cells expressing wild-type CYP2E1 were treated with bicarbonate, and both the soluble and insoluble fractions were separated and analyzed by immunoblot analysis with CYP2E1, TIM23 and Put2 antibodies as indicated.

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the protein was peripherally associated with the inner

membrane and required washing with a high salt

con-centration (0.2 m NaCl) to be released from the

mem-brane (data not shown)

Role of PKA in the mitochondrial targeting of

CYP2E1

The role of PKA in mitochondrial targeting of

CYP2E1 was investigated using two approaches The

first approach involved measuring the level of

mito-chondrial targeting of wild-type CYP2E1 in

PKA-defi-cient (a⁄ c deleted or a ⁄ b deleted) yeast strains The

western blot in Fig 5A shows that in control yeast

cells, the microsomal CYP2E1 content was

approxi-mately 4–6-fold higher than the mitochondrial content,

and the microsome-localized CYP2E1 was highly

sensi-tive to trypsin (Fig 5A, compare lanes 1 and 3) The

mitochondrial CYP2E1 was resistant to externally

added trypsin, and in this regard was similar to the

inner membrane protein TIM23 (Fig 5A, compare

lanes 2 and 4) The microsome-associated CYP2E1 levels in both the PKA subunit a⁄ c and a ⁄ b deleted strains were similar to that in the control yeast strain (Fig 5A, lane 1) As observed with the control yeast, the microsome-associated CYP2E1 in PKA mutant strains was sensitive to trypsin treatment Quantitation

of the gel pattern presented in Fig 5B showed that the mitochondrial CYP2E1 levels were reduced to < 10%

in the a⁄ c mutant and < 3% in the a ⁄ b mutant, as compared to about 25% in the control strain We also tested the targeting to mitochondria of Su9-DHFR, in which the presequence of ATPase subunit 9 of Neuros-pora crassa was fused to a passenger protein, DHFR

As seen in Fig 5A, the level of mitochondrial targeting

of Su9-DHFR, which lacks a canonical PKA phos-phorylation site, was similar in all three cell lines tested CYP2E1 contained a single PKA target site at Ser129, which was shown to be important in mito-chondrial targeting of the protein in COS cells In the second approach, we tested the level of mitochondrial targeting of S129A mutant CYP2E1 in transformed

0 10 20 30 40 50 60 70 80 90 100

WT

Micro Mito

PKA

Δ α/γ

Δ α/β

Δ α/γ

PKA

Δ α/β

Strain background

TIM23

TIM23

2E1

2E1

Su9-DHFR

Su9-DHFR

*

TIM23

Micro

A

B

C

Mito Micro Mito

2E1

WT

Su9-DHFR

+

*

Micro Mito Micro Mito

2E1(S129A)

TIM23

100 72 2 10 % distribution

% distribution 100

Fig 5 Role of PKA-mediated phosphorylation in mitochondrial targeting of CYP2E1 (A) Isolated mitochondrial and microsomal fractions from the wild-type and PKA deletion strains were transformed with CYP2E1 or SU9-DHFR expression cDNA constructs or empty vectors Subcel-lular fractions were subjected to immunoblot analysis following treatment with or without trypsin as indicated TIM23 was used as a mito-chondrial marker (B) The amount of CYP present in the microsomal or mitomito-chondrial fractions obtained from various PKA mutants were quantified and represented as a bar graph (C) Reduced mitochondrial targeting of phosphorylation site mutated CYP2E1 (S129A) Mitochon-dria and microsomal fractions of yeast cells expressing S129A mutant CYP2E1 were treated with or without trypsin and subjected to immu-noblot analysis with CYP2E1 and TIM23 antibodies.

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yeast cells The results in Fig 5C show that, as with

the wild-type protein, full-length mutant protein was

targeted to mitochondria, although at a markedly

reduced level (30–40% as compared to the wild-type

construct) These results collectively show that

PKA-mediated phosphorylation, most likely targeted to the

S129 consensus site, is very important for

mitochon-drial targeting of CYP2E1 protein

Mitochondrial targeting of CYP2B1 in yeast cells

We used the protease-deficient strain pep4D for testing

the mitochondrial targeting of rat CYP2B1 The

western blot in Fig 6A shows that both ER and

mitochondrial preparations from transformed yeast

cells contained CYP2B1 protein, with about 25% of

protein in the mitochondrial fraction As in previous

experiments, the mitochondrial preparations contained

TIM23 protein, whereas the microsomes lacked signifi-cant levels of TIM23 The western blot in Fig 6B also shows that the microsome-targeted CYP2B1 was sensi-tive to trypsin treatment, whereas the mitochondrial protein showed significant resistance, suggesting an intramitochondrial location

CYP contents and catalytic activities With the aim of correlating the levels of expression of various apoproteins in yeast with CYP contents, we measured the P450-heme contents by CO-reduced spec-tra As shown in Fig 7, mitochondrial isolates from + 33⁄ 1A1-expressing yeast cells yielded a CO reduced and dithionite reduced spectrum with a peak at

448 nm No peak was observed with mitochondria from cells transformed with empty vector (data not shown) Additionally, we did not detect any character-istic spectrum with mitochondria from cells expressing + 33⁄ 1A1 mutant constructs (data not shown) Figure 7B shows the P450-heme contents of mito-chondria and microsomal fractions from yeast strains expressing various CYP constructs based on CO differ-ence spectral analysis Consistent with the negligible mitochondrial localization of full-length CYP1A1, we detected no significant CYP in the mitochondrial isolates However, the microsomal fraction showed a high (6.5 nmolÆmg)1) CYP content Cells expressing + 5⁄ 1A1 showed nearly equal CYP contents in the mitochondrial and microsomal fraction Cells express-ing + 33⁄ 1A1 showed no detectable CYP in the microsomal fraction, but a high (3.5 nmolÆmg)1) level

of CYP in mitochondria Cells expressing full-length CYP2E1 showed about 300 pmolÆmg)1 CYP in the microsomes and 55 pmolÆmg)1 in mitochondria The mitochondrial fraction from CYP2B1-expressing cells showed about 50 pmolÆmg)1CYP

As shown in Fig 8A, the microsomal fraction from full-length CYP1A1- and + 5⁄ 1A1-expressing cells

0.005

0.055

0.105

0.155

0.205

Wave length (nm)

+331A1 mito

CYP450

2B1

B A

ND

pmole/mg microsomal protein

pmole/mg mitochondrial protein Fig 7 Mitochondrial CYP contents in yeast

cells expressing CYP1A1, CYP2E1 and CYP2B1 proteins (A) The reduced CO spec-tra of the mitochondrial fraction expressing + 331A1 The reduced CO spectrum was performed essentially as described by Anandatheerthavarada et al [5] (B) Relative levels of CYP in mitochondria and micro-somes from cells expressing different CYP proteins CYP content was measured by CO difference spectra as described in (A) The values are the mean of three experiments.

Micro Mito

25

35

47

62

81

kDa

TIM23

2B1

Micro Mito

Trypsin +

+

Fig 6 Immunoblot analysis of PeP4D strain expressing full-length

CYP2B1 Isolated mitochondrial or microsomal fractions were

trea-ted with (B) or without (A) trypsin, and subjectrea-ted to SDS ⁄ PAGE

and immunoblot analysis with CYP2B1 and TIM23 antibodies.

Trang 9

showed high activity of ethoxyresorufin O-dealkylation

(EROD), which is a specific marker enzyme for

ER-associated CYP1A1 +33⁄ 1A1-expressing cells,

how-ever, showed very low ERND activity The latter is

consistent with the microsomal CYP content of cells

expressing + 33⁄ CYP1A1 (Fig 7) The mitochondrial

isolates from all these three cell types showed very low

EROD activity The erythromycin N-demethylase

(ERND) activity pattern (Fig 8B) was significantly

different from the EROD activity pattern (Fig 8A)

The microsomal fraction of cells expressing full-length

CYP1A1 and + 5⁄ 1A1 showed relatively low ERND

activity Similarly, consistent with the low or

non-significant mitochondrial localization of full-length

CYP1A1, mitochondria from these cells also showed

very low activity The mitochondrial isolates from

+ 5⁄ 1A1- and + 33 ⁄ 1A1-expressing cells, however,

showed high ERND activity (2.0–2.5 nmolÆmg)1) with

the endogenous yeast FDX + FDXR Expression of

mutant 33⁄ 1A1 with impaired mitochondrial targeting

showed vastly reduced mitochondrial ERND activity

Our results on ERND activity of

mitochondria-targeted CYP1A1 supported by mitochondrial

FDX1 + FDXR are consistent with previous studies

from our laboratory [32,33] showing altered catalytic

property of mitochondria-targeted rat and mouse

CYP1A1

As shown in Fig 8C, both microsomal and

mito-chondrial fractions from CYP2B1 cDNA-transformed

cells show benzoxyresorufin O-dealkylation (BROD) activity The BROD was reduced by about 60% when the mitochondrial or microsomal fractions were prein-cubated with CYP2B1 antibody, indicating the specific-ity of the assay

As shown in Fig 9A, both microsomal and mitochon-drial fractions from wild-type yeast cells transformed with CYP2E1 cDNA showed nitrosodimethylamine N-demethylase (NDMA-d) activity The activities of both the microsomal CYP2E1 and mitochondrial CYP2E1 were dependent on the addition of NADPH (Fig 9A) The catalytic activities were reduced when the mitochondrial or microsomal enzymes were prein-cubated with CYP2E1 antibody or SKF-525, a general inhibitor of CYPs These results suggest the specificity

of the assay We did not observe any significant increases in the activity of mitochondrial CYP2E1 after supplementing the reaction with purified bovine FDX1 + FDXR, possibly because of adequate endo-genous FDX1 + FDXR in these mitochondrial prepa-rations (Fig 9A) Additionally, the activity with the mitochondrial fraction was inhibited by 50% after addi-tion of polyclonal antibody to human FDX1 (Fig 9A), confirming the role of endogenous FDX + FDXR in supporting the activity

To further confirm the role of endogenous FDX + FDXR in supporting the catalytic activity, we transformed the FDX (Yah1)- and FDXR (Arh1)-depleted yeast cells with CYP2E1 Expression of

0 0.05 0.1 0.15 0.2

0.25

Micro Mito

CYP2B1: -

- -

-+ -+ + + Anti-2B1: + +

BROD ACTIVITY

ERND ACTIVITY

0 0.5

1 1.5

2 2.5

3

1A1 +5 +33

Micro Mito

EROD ACTIVITY

A

C

B

0 0.2 0.4 0.6 0.8

1 1.2 1.4 1.6 1.8

2

Micro Mito

Fig 8 Metabolic activities of the

micro-somal and mitochondrial CYPs in

trans-formed yeast cells Microsomes and

digitonin-treated mitoplasts from cells

expressing various CYP variants were

assayed for their enzyme activities as

indi-cated in Experimental procedures (A) and

(B) represent the EROD and ERND activities

of cells transformed with various CYP1A1s,

and (C) represents the BROD activity of

cells transformed with CYP2B1 constructs

as indicated.

Trang 10

CYP2E1 in Yah1-depleted cells turned out to be lethal.

We therefore analyzed the Arh1-depleted cells

express-ing CYP2E1 The catalytic activity of the mitochondrial

fraction was reduced by about 60% in FDXR-depleted

cells (Fig 9B) However, the activity with the

mito-chondrial fraction was restored by the addition of

puri-fied bovine FDX + Fdr These results confirm that

yeast mitochondrial FDX + FDXR is capable of

sup-porting the catalytic activity of mammalian CYPs

Discussion

A large majority of mitochondrial proteins are

encoded by nuclear genes, synthesized in the cytoplasm

and post-translationally transported to mitochondria

The mitochondrial proteome in mammalian cells is

estimated to consist of well over 1500 proteins

imported from the cytoplasm [34] Several

mitochon-drial matrix-targeted proteins contain an N-terminal

extension or ‘presequence’ that is cleaved upon import

into mitochondria [35] However, the current estimates

are that more than 50% of the

mitochondrial-associ-ated proteins lack the canonical mitochondria-targeting

signals, and the precise mechanisms by which these

proteins are translocated to the mitochondrial

com-partment remain unclear [35,36] The mitochondrial

inner membrane-associated carrier protein, uncoupler

proteins and outer membrane proteins belong to this

latter class [37,38] Additionally, the bimodal targeting

of CYPs to the ER and mitochondria, Alzheimer’s amyloid precursor protein to the plasma membrane and mitochondria, and translocation of the cytosolic glutathione S-transferases to the mitochondrial matrix compartment, probably represent the targeting of non-canonical signal-containing proteins to the mitochon-drial compartment [4–6,12,39] We have shown that xenobiotic-inducible CYPs such as rat CYP1A1, CYP2E1 and CYP2B1, and mouse CYP1A1, contain chimeric noncanonical-targeting signals that are capa-ble of targeting proteins to both the ER and mitochon-dria [5,11,12] Our results showed that the cryptic mitochondria-targeting signals present at residues 29–40 in various CYP proteins are activated by two different mechanisms: (a) proteolytic processing at the N-terminus by a cytosolic endoprotease, resulting in the exposure of cryptic mitochondrial targeting signal,

as in the case of CYP1A1 [4]; and (b) PKA- or protein kinase C-mediated phosphorylation of nascent chains either at the N-terminus (Ser128 or Ser129) or the C-terminus, which promotes the mitochondrial target-ing of CYP2E1, CYP2B1, and GSTA4-4 [6,12,40] In this study, we show that bimodal targeting of CYP1A1, CYP2E1 and CYP2B1 are conserved in the heterologous cell system Saccharomyces cerevisiae The N-terminal four or 32 amino acid sequence (+ 5⁄ 1A1 or + 33 ⁄ 1A1) of CYP1A1 exposes the cryp-tic mitochondria-targeting sequence at positions 33–39

of the protein, thus targeting the + 331A1 protein

0 0.5 1 1.5 2 2.5 3 3.5 4 4.5

Cell Fractions

NADPH

FDR& FDX

Ant-FDX

SKF-525

Anti-2E1

Anti-IgG

Wt cells expressing CYP2E1

0 0.5 1 1.5 2 2.5 3 3.5 4

Mito

Cell Fractions NADPH FDR& FDX FDXR depleted cells expressing CYP2E1

Fig 9 Mitochondrial CYP2E1 activity in wild-type and FDXR-depleted yeast strains Mitochondrial and microsomal NMDA-d activity in (A) wild-type cells expressing CYP2E1 and (B) FDXR-depleted cells expressing CYP2E1 Reactions were carried out as described in Experi-mental procedures, using 50 lg of mitochondria or microsomal proteins NADPH (1 m M ), FDX + FDXR (1 lg each), antibody to FDX (2 lg), antibody to CYP2E1 (1 lg), preimmune IgG (anti-IgG) and SKF-525 (0.1 m M ) were added to the reaction before initiating the enzyme activity

by adding the dimethylnitrosomine (4 m M ) Depletion of FDXR was carried out as described in Experimental procedures Details of enzyme assays are given in Experimental procedures.

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