Biopolym. Cell. 2007; 23(2):67-85.
Reviews
Structure-functional characterization of cytochrome P4502E1 (CYP2E1)
1Danko I. M., 1Chaschin N. A.
  1. Institute of Molecular Biology and Genetics, NAS of Ukraine
    150, Akademika Zabolotnoho Str., Kyiv, Ukraine, 03680

Abstract

This review summarizes data on expression level and localization, structure and functional properties of cytochrome P4502E1 (CYP2E1). Induction of CYP2E1 synthesis and activity by compounds with various chemical structures and under certain pathophysiological states is considered. Special emphasis is placed on CYP2E1 expression inhibitors. The latest data on CYP2E1 expression regulation and degradation mechanisms are analyze
Keywords: cytochrome P4502E1 (CYP2E1), expression, inductors and inhibitors, expression regulation, oxidative metabolism of ethanol

References

[1] Anzenbacher P, Anzenbacherov? E. Cytochromes P450 and metabolism of xenobiotics. Cell Mol Life Sci. 2001;58(5-6):737-47.
[2] Umeno M, McBride OW, Yang CS, Gelboin HV, Gonzalez FJ. Human ethanol-inducible P450IIE1: complete gene sequence, promoter characterization, chromosome mapping, and cDNA-directed expression. Biochemistry. 1988;27(25):9006-13.
[3] Harada S. [Classification of alcohol metabolizing enzymes and polymorphisms--specificity in Japanese]. Nihon Arukoru Yakubutsu Igakkai Zasshi. 2001;36(2):85-106.
[4] Lewis DF, Bird MG, Dickins M, Lake BG, Eddershaw PJ, Tarbit MH, Goldfarb PS. Molecular modelling of human CYP2E1 by homology with the CYP102 haemoprotein domain: investigation of the interactions of substrates and inhibitors within the putative active site of the human CYP2E1 isoform. Xenobiotica. 2000;30(1):1-25.
[5] Lee SS, Buters JT, Pineau T, Fernandez-Salguero P, Gonzalez FJ. Role of CYP2E1 in the hepatotoxicity of acetaminophen. J Biol Chem. 1996;271(20):12063-7.
[6] Song BJ, Gelboin HV, Park SS, Yang CS, Gonzalez FJ. Complementary DNA and protein sequences of ethanol-inducible rat and human cytochrome P-450s. Transcriptional and post-transcriptional regulation of the rat enzyme. J Biol Chem. 1986;261(35):16689-97.
[7] Ingelman-Sundberg M, Ronis MJ, Lindros KO, Eliasson E, Zhukov A. Ethanol-inducible cytochrome P4502E1: regulation, enzymology and molecular biology. Alcohol Alcohol Suppl. 1994;2:131-9.
[8] Khani SC, Zaphiropoulos PG, Fujita VS, Porter TD, Koop DR, Coon MJ. cDNA and derived amino acid sequence of ethanol-inducible rabbit liver cytochrome P-450 isozyme 3a (P-450ALC). Proc Natl Acad Sci U S A. 1987;84(3):638-42.
[9] Danko IM, Odynets KA, Kitam VO, Chashchin NA. [Computer modeling of cytochrome P450 2E1 three-dimensional structure]. Ukr Biokhim Zh. 2006;78(2):154-62.
[10] Park JY, Harris D. Construction and assessment of models of CYP2E1: predictions of metabolism from docking, molecular dynamics, and density functional theoretical calculations. J Med Chem. 2003;46(9):1645-60.
[11] Lewis DF, Lake BG, Bird MG, Loizou GD, Dickins M, Goldfarb PS. Homology modelling of human CYP2E1 based on the CYP2C5 crystal structure: investigation of enzyme-substrate and enzyme-inhibitor interactions. Toxicol In Vitro. 2003;17(1):93-105.
[12] Tan Y, White SP, Paranawithana SR, Yang CS. A hypothetical model for the active site of human cytochrome P4502E1. Xenobiotica. 1997;27(3):287-99.
[13] Mackman R, Guo Z, Guengerich FP, Ortiz de Montellano PR. Active site topology of human cytochrome P450 2E1. Chem Res Toxicol. 1996;9(1):223-6.
[14] Lewis DF. Homology modelling of human CYP2 family enzymes based on the CYP2C5 crystal structure. Xenobiotica. 2002;32(4):305-23.
[15] Banerjee A, Kocarek TA, Novak RF. Identification of a ubiquitination-Target/Substrate-interaction domain of cytochrome P-450 (CYP) 2E1. Drug Metab Dispos. 2000;28(2):118-24.
[16] Johansson I, Lindros KO, Eriksson H, Ingelman-Sundberg M. Transcriptional control of CYP2E1 in the perivenous liver region and during starvation. Biochem Biophys Res Commun. 1990;173(1):331-8.
[17] Tanaka E, Terada M, Misawa S. Cytochrome P450 2E1: its clinical and toxicological role. J Clin Pharm Ther. 2000;25(3):165-75.
[18] Nishimura M, Yaguti H, Yoshitsugu H, Naito S, Satoh T. Tissue distribution of mRNA expression of human cytochrome P450 isoforms assessed by high-sensitivity real-time reverse transcription PCR. Yakugaku Zasshi. 2003;123(5):369-75.
[19] Zerilli A, Lucas D, Amet Y, Beauge F, Volant A, Floch HH, Berthou F, Menez JF. Cytochrome P-450 2E1 in rat liver, kidney and lung microsomes after chronic administration of ethanol either orally or by inhalation. Alcohol Alcohol. 1995;30(3):357-65.
[20] Lechevrel M, Casson AG, Wolf CR, Hardie LJ, Flinterman MB, Montesano R, Wild CP. Characterization of cytochrome P450 expression in human oesophageal mucosa. Carcinogenesis. 1999;20(2):243-8.
[21] Runge DM, Stock TW, Lehmann T, Taege C, Bernauer U, Stolz DB, Hofmann S, Foth H. Expression of cytochrome P450 2E1 in normal human bronchial epithelial cells and activation by ethanol in culture. Arch Toxicol. 2001;75(6):335-45.
[22] Ding X, Kaminsky LS. Human extrahepatic cytochromes P450: function in xenobiotic metabolism and tissue-selective chemical toxicity in the respiratory and gastrointestinal tracts. Annu Rev Pharmacol Toxicol. 2003;43:149-73.
[23] Waxman DJ, Morrissey JJ, LeBlanc GA. Female-predominant rat hepatic P-450 forms j (IIE1) and 3 (IIA1) are under hormonal regulatory controls distinct from those of the sex-specific P-450 forms. Endocrinology. 1989;124(6):2954-66.
[24] Dicker E, Cederbaum AI. Increased oxidation of dimethylnitrosamine in pericentral microsomes after pyrazole induction of cytochrome P-4502E1. Alcohol Clin Exp Res. 1991;15(6):1072-6.
[25] Ingelman-Sundberg M, Johansson I, Penttil? KE, Glaumann H, Lindros KO. Centrilobular expression of ethanol-inducible cytochrome P-450 (IIE1) in rat liver. Biochem Biophys Res Commun. 1988;157(1):55-60.
[26] Takahashi T, Lasker JM, Rosman AS, Lieber CS. Induction of cytochrome P-4502E1 in the human liver by ethanol is caused by a corresponding increase in encoding messenger RNA. Hepatology. 1993;17(2):236-45.
[27] Lieber CS. The discovery of the microsomal ethanol oxidizing system and its physiologic and pathologic role. Drug Metab Rev. 2004;36(3-4):511-29.
[28] Ronis MJ, Johansson I, Hultenby K, Lagercrantz J, Glaumann H, Ingelman-Sundberg M. Acetone-regulated synthesis and degradation of cytochrome P450E1 and cytochrome P4502B1 in rat liver . Eur J Biochem. 1991;198(2):383-9.
[29] Wu D, Cederbaum AI. Presence of functionally active cytochrome P-450IIE1 in the plasma membrane of rat hepatocytes. Hepatology. 1992;15(3):515-24.
[30] Gonzalez FJ. Role of cytochromes P450 in chemical toxicity and oxidative stress: studies with CYP2E1. Mutat Res. 2005;569(1-2):101-10.
[31] Lucas D, Ferrara R, Gonzales E, Albores A, Manno M, Berthou F. Cytochrome CYP2E1 phenotyping and genotyping in the evaluation of health risks from exposure to polluted environments. Toxicol Lett. 2001;124(1-3):71-81.
[32] Guengerich FP. Metabolism of chemical carcinogens. Carcinogenesis. 2000;21(3):345-51.
[33] Guengerich FP. Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity. Chem Res Toxicol. 2001;14(6):611-50.
[34] Bell-Parikh LC, Guengerich FP. Kinetics of cytochrome P450 2E1-catalyzed oxidation of ethanol to acetic acid via acetaldehyde. J Biol Chem. 1999;274(34):23833-40.
[35] Banerjee S, Shang TQ, Wilson AM, Moore AL, Strand SE, Gordon MP, Lafferty Doty S. Expression of functional mammalian P450 2E1 in hairy root cultures. Biotechnol Bioeng. 2002;77(4):462-6.
[36] Burim RV, Canalle R, Martinelli Ade L, Takahashi CS. Polymorphisms in glutathione S-transferases GSTM1, GSTT1 and GSTP1 and cytochromes P450 CYP2E1 and CYP1A1 and susceptibility to cirrhosis or pancreatitis in alcoholics. Mutagenesis. 2004;19(4):291-8.
[37] Lieber CS, DeCarli LM. Hepatic microsomal ethanol-oxidizing system. In vitro characteristics and adaptive properties in vivo. J Biol Chem. 1970;245(10):2505-12.
[38] Novak RF, Woodcroft KJ. The alcohol-inducible form of cytochrome P450 (CYP 2E1): role in toxicology and regulation of expression. Arch Pharm Res. 2000;23(4):267-82.
[39] Valentine JL, Lee SS, Seaton MJ, Asgharian B, Farris G, Corton JC, Gonzalez FJ, Medinsky MA. Reduction of benzene metabolism and toxicity in mice that lack CYP2E1 expression. Toxicol Appl Pharmacol. 1996;141(1):205-13.
[40] Kessova I, Cederbaum AI. CYP2E1: biochemistry, toxicology, regulation and function in ethanol-induced liver injury. Curr Mol Med. 2003;3(6):509-18.
[41] Yamazaki H, Inui Y, Yun CH, Guengerich FP, Shimada T. Cytochrome P450 2E1 and 2A6 enzymes as major catalysts for metabolic activation of N-nitrosodialkylamines and tobacco-related nitrosamines in human liver microsomes. Carcinogenesis. 1992;13(10):1789-94.
[42] Patten CJ, Smith TJ, Murphy SE, Wang MH, Lee J, Tynes RE, Koch P, Yang CS. Kinetic analysis of the activation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone by heterologously expressed human P450 enzymes and the effect of P450-specific chemical inhibitors on this activation in human liver microsomes. Arch Biochem Biophys. 1996;333(1):127-38.
[43] Bellec G, Goasduff T, Dreano Y, Menez JF, Berthou F. Effect of the length of alkyl chain on the cytochrome P450 dependent metabolism of N-diakylnitrosamines. Cancer Lett. 1996;100(1-2):115-23.
[44] Yoo JS, Guengerich FP, Yang CS. Metabolism of N-nitrosodialkylamines by human liver microsomes. Cancer Res. 1988;48(6):1499-504.
[45] Gan J, Skipper PL, Tannenbaum SR. Oxidation of 2,6-dimethylaniline by recombinant human cytochrome P450s and human liver microsomes. Chem Res Toxicol. 2001;14(6):672-7.
[46] Wang H, Chanas B, Ghanayem BI. Cytochrome P450 2E1 (CYP2E1) is essential for acrylonitrile metabolism to cyanide: comparative studies using CYP2E1-null and wild-type mice. Drug Metab Dispos. 2002;30(8):911-7.
[47] Adas F, Sala?n JP, Berthou F, Picart D, Simon B, Amet Y. Requirement for omega and (omega;-1)-hydroxylations of fatty acids by human cytochromes P450 2E1 and 4A11. J Lipid Res. 1999;40(11):1990-7.
[48] Amato G, Grasso E, Longo V, Gervasi PG. Oxidation of N,N-dimethylformamide and N,N-diethylformamide by human liver microsomes and human recombinant P450s. Toxicol Lett. 2001;124(1-3):11-9.
[49] Kapucuoglu N, Coban T, Raunio H, Pelkonen O, Edwards RJ, Boobis AR, Iscan M. Immunohistochemical demonstration of the expression of CYP2E1 in human breast tumour and non-tumour tissues. Cancer Lett. 2003;196(2):153-9.
[50] Aviram M, Kent UM, Hollenberg PF. Microsomal cytochromes P450 catalyze the oxidation of low density lipoprotein. Atherosclerosis. 1999;143(2):253-60.
[51] Meskar A, Plee-Gautier E, Amet Y, Berthou F, Lucas D. [Alcohol-xenobiotic interactions. Role of cytochrome P450 2E1]. Pathol Biol (Paris). 2001;49(9):696-702.
[52] Walubo A, Barr S, Abraham AM, Coetsee C. The role of cytochrome-P450 inhibitors in the prevention of hepatotoxicity after paracetamol overdose in rats. Hum Exp Toxicol. 2004;23(1):49-54.
[53] Bessems JG, Vermeulen NP. Paracetamol (acetaminophen)-induced toxicity: molecular and biochemical mechanisms, analogues and protective approaches. Crit Rev Toxicol. 2001;31(1):55-138.
[54] Halmes NC, Samokyszyn VM, Hinton TW, Hinson JA, Pumford NR. The acetaminophen regioisomer 3'-hydroxyacetanilide inhibits and covalently binds to cytochrome P450 2E1. Toxicol Lett. 1998;94(1):65-71.
[55] Spracklin DK, Emery ME, Thummel KE, Kharasch ED. Concordance between trifluoroacetic acid and hepatic protein trifluoroacetylation after disulfiram inhibition of halothane metabolism in rats. Acta Anaesthesiol Scand. 2003;47(6):765-70.
[56] Zhao P, Kalhorn TF, Slattery JT. Selective mitochondrial glutathione depletion by ethanol enhances acetaminophen toxicity in rat liver. Hepatology. 2002;36(2):326-35.
[57] Takahashi S, Takahashi T, Mizobuchi S, Matsumi M, Morita K, Miyazaki M, Namba M, Akagi R, Hirakawa M. Increased cytotoxicity of carbon tetrachloride in a human hepatoma cell line overexpressing cytochrome P450 2E1. J Int Med Res. 2002;30(4):400-5.
[58] Wong FW, Chan WY, Lee SS. Resistance to carbon tetrachloride-induced hepatotoxicity in mice which lack CYP2E1 expression. Toxicol Appl Pharmacol. 1998;153(1):109-18.
[59] Boll M, Weber LW, Becker E, Stampfl A. Mechanism of carbon tetrachloride-induced hepatotoxicity. Hepatocellular damage by reactive carbon tetrachloride metabolites. Z Naturforsch C. 2001;56(7-8):649-59. PubMed PMID: 12708612.
[60] Weber LW, Boll M, Stampfl A. Hepatotoxicity and mechanism of action of haloalkanes: carbon tetrachloride as a toxicological model. Crit Rev Toxicol. 2003;33(2):105-36.
[61] Ekstr?m G, von Bahr C, Ingelman-Sundberg M. Human liver microsomal cytochrome P-450IIE1. Immunological evaluation of its contribution to microsomal ethanol oxidation, carbon tetrachloride reduction and NADPH oxidase activity. Biochem Pharmacol. 1989;38(4):689-93.
[62] Zhukov A, Ingelman-Sundberg M. Relationship between cytochrome P450 catalytic cycling and stability: fast degradation of ethanol-inducible cytochrome P450 2E1 (CYP2E1) in hepatoma cells is abolished by inactivation of its electron donor NADPH-cytochrome P450 reductase. Biochem J. 1999;340 (Pt 2):453-8.
[63] Cederbaum AI, Wu D, Mari M, Bai J. CYP2E1-dependent toxicity and oxidative stress in HepG2 cells. Free Radic Biol Med. 2001;31(12):1539-43.
[64] Kalapos MP. On the mammalian acetone metabolism: from chemistry to clinical implications. Biochim Biophys Acta. 2003;1621(2):122-39.
[65] Bondoc FY, Bao Z, Hu WY, Gonzalez FJ, Wang Y, Yang CS, Hong JY. Acetone catabolism by cytochrome P450 2E1: studies with CYP2E1-null mice. Biochem Pharmacol. 1999;58(3):461-3.
[66] Amet Y, Adas F, Nanji AA. Fatty acid omega- and (omega-1)-hydroxylation in experimental alcoholic liver disease: relationship to different dietary fatty acids. Alcohol Clin Exp Res. 1998;22(7):1493-500.
[67] Coon MJ. Enzyme ingenuity in biological oxidations: a trail leading to cytochrome p450. J Biol Chem. 2002;277(32):28351-63.
[68] Monostory K, Hazai E, Vereczkey L. Inhibition of cytochrome P450 enzymes participating in p-nitrophenol hydroxylation by drugs known as CYP2E1 inhibitors. Chem Biol Interact. 2004;147(3):331-40.
[69] Wolf KK, Wood SG, Bement JL, Sinclair PR, Wrighton SA, Jeffery E, Gonzalez FJ, Sinclair JF. Role of mouse CYP2E1 in the O-hydroxylation of p-nitrophenol: comparison of activities in hepatic microsomes from Cyp2e1(-/-) and wild-type mice. Drug Metab Dispos. 2004;32(7):681-4.
[70] Park KS, Sohn DH, Veech RL, Song BJ. Translational activation of ethanol-inducible cytochrome P450 (CYP2E1) by isoniazid. Eur J Pharmacol. 1993;248(1):7-14.
[71] Peter R, B?cker R, Beaune PH, Iwasaki M, Guengerich FP, Yang CS. Hydroxylation of chlorzoxazone as a specific probe for human liver cytochrome P-450IIE1. Chem Res Toxicol. 1990;3(6):566-73.
[72] Chen TL, Chen TG, Tai YT, Chang HC, Chen RM, Lin CJ, Ueng TH. Propofol inhibits renal cytochrome P450 activity and enflurane defluorination in vitro in hamsters. Can J Anaesth. 2000;47(7):680-6.
[73] Bolt HM, Roos PH, Thier R. The cytochrome P-450 isoenzyme CYP2E1 in the biological processing of industrial chemicals: consequences for occupational and environmental medicine. Int Arch Occup Environ Health. 2003;76(3):174-85.
[74] Amato G, Longo V, Mazzaccaro A, Gervasi PG. Chlorzoxazone 6-hydroxylase and p-nitrophenol hydroxylase as the most suitable activities for assaying cytochrome P450 2E1 in cynomolgus monkey liver. Drug Metab Dispos. 1998;26(5):483-9.
[75] Snawder JE, Lipscomb JC. Interindividual variance of cytochrome P450 forms in human hepatic microsomes: correlation of individual forms with xenobiotic metabolism and implications in risk assessment. Regul Toxicol Pharmacol. 2000;32(2):200-9.
[76] Hu Y, Hakkola J, Oscarson M, Ingelman-Sundberg M. Structural and functional characterization of the 5'-flanking region of the rat and human cytochrome P450 2E1 genes: identification of a polymorphic repeat in the human gene. Biochem Biophys Res Commun. 1999;263(2):286-93.
[77] Chen XP, Han XM, Jiang CH, Huang SL, Liu ZQ, Zhu B, Zhou G, Zhou HH. Phenotype distribution and gender-related differences of CYP2E1 activity in a Chinese population. Xenobiotica. 2002;32(11):1053-62.
[78] Powell H, Kitteringham NR, Pirmohamed M, Smith DA, Park BK. Expression of cytochrome P4502E1 in human liver: assessment by mRNA, genotype and phenotype. Pharmacogenetics. 1998;8(5):411-21.
[79] Kim RB, O'Shea D. Interindividual variability of chlorzoxazone 6-hydroxylation in men and women and its relationship to CYP2E1 genetic polymorphisms. Clin Pharmacol Ther. 1995;57(6):645-55.
[80] McCarver DG, Byun R, Hines RN, Hichme M, Wegenek W. A genetic polymorphism in the regulatory sequences of human CYP2E1: association with increased chlorzoxazone hydroxylation in the presence of obesity and ethanol intake. Toxicol Appl Pharmacol. 1998;152(1):276-81.
[81] Marchand LL, Wilkinson GR, Wilkens LR. Genetic and dietary predictors of CYP2E1 activity: a phenotyping study in Hawaii Japanese using chlorzoxazone. Cancer Epidemiol Biomarkers Prev. 1999;8(6):495-500.
[82] Kim RB, Yamazaki H, Chiba K, O'Shea D, Mimura M, Guengerich FP, Ishizaki T, Shimada T, Wilkinson GR. In vivo and in vitro characterization of CYP2E1 activity in Japanese and Caucasians. J Pharmacol Exp Ther. 1996;279(1):4-11.
[83] Poland RA, Lin KM, Nuccio C, Wilkinson GR. Cytochrome P450 2E1 and 3A activities do not differ between Mexicans and European Americans. Clin Pharmacol Ther. 2002;72(3):288-93.
[84] Simi A, Ingelman-Sundberg M. Post-translational inhibition of cytochrome P-450 2E1 expression by chlomethiazole in Fao hepatoma cells. J Pharmacol Exp Ther. 1999;289(2):847-52.
[85] Ohashi Y, Yamada K, Takemoto I, Mizutani T, Saeki K. Inhibition of human cytochrome P450 2E1 by halogenated anilines, phenols, and thiophenols. Biol Pharm Bull. 2005;28(7):1221-3.
[86] Wargovich MJ. Diallylsulfide and allylmethylsulfide are uniquely effective among organosulfur compounds in inhibiting CYP2E1 protein in animal models. J Nutr. 2006;136(3 Suppl):832S-834S.
[87] Yang CS, Chhabra SK, Hong JY, Smith TJ. Mechanisms of inhibition of chemical toxicity and carcinogenesis by diallyl sulfide (DAS) and related compounds from garlic. J Nutr. 2001;131(3s):1041S-5S.
[88] Hu Y, Mishin V, Johansson I, von Bahr C, Cross A, Ronis MJ, Badger TM, Ingelman-Sundberg M. Chlormethiazole as an efficient inhibitor of cytochrome P450 2E1 expression in rat liver. J Pharmacol Exp Ther. 1994;269(3):1286-91.
[89] Hakkola J, Hu Y, Ingelman-Sundberg M. Mechanisms of down-regulation of CYP2E1 expression by inflammatory cytokines in rat hepatoma cells. J Pharmacol Exp Ther. 2003;304(3):1048-54.
[90] Eliasson E, Johansson I, Ingelman-Sundberg M. Ligand-dependent maintenance of ethanol-inducible cytochrome P-450 in primary rat hepatocyte cell cultures. Biochem Biophys Res Commun. 1988;150(1):436-43.
[91] Song BJ, Veech RL, Park SS, Gelboin HV, Gonzalez FJ. Induction of rat hepatic N-nitrosodimethylamine demethylase by acetone is due to protein stabilization. J Biol Chem. 1989;264(6):3568-72.
[92] Woodcroft KJ, Novak RF. Insulin differentially affects xenobiotic-enhanced, cytochrome P-450 (CYP)2E1, CYP2B, CYP3A, and CYP4A expression in primary cultured rat hepatocytes. J Pharmacol Exp Ther. 1999;289(2):1121-7.
[93] Kim SG, Novak RF. Induction of rat hepatic P450IIE1 (CYP 2E1) by pyridine: evidence for a role of protein synthesis in the absence of transcriptional activation. Biochem Biophys Res Commun. 1990;166(3):1072-9.
[94] Brown BL, Allis JW, Simmons JE, House DE. Fasting for less than 24 h induces cytochrome P450 2E1 and 2B1/2 activities in rats. Toxicol Lett. 1995;81(1):39-44.
[95] Lucas D, M?nez C, Girre C, Berthou F, Bod?nez P, Joannet I, Hispard E, Bardou LG, M?nez JF. Cytochrome P450 2E1 genotype and chlorzoxazone metabolism in healthy and alcoholic Caucasian subjects. Pharmacogenetics. 1995;5(5):298-304.
[96] Woodcroft KJ, Hafner MS, Novak RF. Insulin signaling in the transcriptional and posttranscriptional regulation of CYP2E1 expression. Hepatology. 2002;35(2):263-73.
[97] Wang Z, Hall SD, Maya JF, Li L, Asghar A, Gorski JC. Diabetes mellitus increases the in vivo activity of cytochrome P450 2E1 in humans. Br J Clin Pharmacol. 2003;55(1):77-85.
[98] Yun YP, Casazza JP, Sohn DH, Veech RL, Song BJ. Pretranslational activation of cytochrome P450IIE during ketosis induced by a high fat diet. Mol Pharmacol. 1992;41(3):474-9.
[99] Woodcroft KJ, Novak RF. Xenobiotic-enhanced expression of cytochromes P450 2E1 and 2B in primary cultured rat hepatocytes. Drug Metab Dispos. 1998;26(4):372-8.
[100] Kocarek TA, Zangar RC, Novak RF. Post-transcriptional regulation of rat CYP2E1 expression: role of CYP2E1 mRNA untranslated regions in control of translational efficiency and message stability. Arch Biochem Biophys. 2000;376(1):180-90.
[101] Ueno T, Gonzalez FJ. Transcriptional control of the rat hepatic CYP2E1 gene. Mol Cell Biol. 1990;10(9):4495-505.
[102] Goasduff T, Cederbaum AI. CYP2E1 degradation by in vitro reconstituted systems: role of the molecular chaperone hsp90. Arch Biochem Biophys. 2000;379(2):321-30.
[103] Morishima Y, Peng HM, Lin HL, Hollenberg PF, Sunahara RK, Osawa Y, Pratt WB. Regulation of cytochrome P450 2E1 by heat shock protein 90-dependent stabilization and CHIP-dependent proteasomal degradation. Biochemistry. 2005;44(49):16333-40.
[104] Son MH, Kang KW, Kim EJ, Ryu JH, Cho H, Kim SH, Kim WB, Kim SG. Role of glucose utilization in the restoration of hypophysectomy-induced hepatic cytochrome P450 2E1 by growth hormone in rats. Chem Biol Interact. 2000;127(1):13-28.
[105] Chen GF, Ronis MJ, Ingelman-Sundberg M, Badger TM. Hormonal regulation of microsomal cytochrome P4502E1 and P450 reductase in rat liver and kidney. Xenobiotica. 1999;29(5):437-51.
[106] Kunitoh S, Imaoka S, Hiroi T, Yabusaki Y, Monna T, Funae Y. Acetaldehyde as well as ethanol is metabolized by human CYP2E1. J Pharmacol Exp Ther. 1997;280(2):527-32.
[107] Tsutsumi M, Lasker JM, Takahashi T, Lieber CS. In vivo induction of hepatic P4502E1 by ethanol: role of increased enzyme synthesis. Arch Biochem Biophys. 1993;304(1):209-18.
[108] Lu Y, Cederbaum AI. Cisplatin-induced hepatotoxicity is enhanced by elevated expression of cytochrome P450 2E1. Toxicol Sci. 2006;89(2):515-23.
[109] Badger TM, Huang J, Ronis M, Lumpkin CK. Induction of cytochrome P450 2E1 during chronic ethanol exposure occurs via transcription of the CYP 2E1 gene when blood alcohol concentrations are high. Biochem Biophys Res Commun. 1993;190(3):780-5.
[110] Ronis MJ, Huang J, Crouch J, Mercado C, Irby D, Valentine CR, Lumpkin CK, Ingelman-Sundberg M, Badger TM. Cytochrome P450 CYP 2E1 induction during chronic alcohol exposure occurs by a two-step mechanism associated with blood alcohol concentrations in rats. J Pharmacol Exp Ther. 1993;264(2):944-50.
[111] Roberts BJ. Evidence of proteasome-mediated cytochrome P-450 degradation. J Biol Chem. 1997;272(15):9771-8.
[112] Eliasson E, Mkrtchian S, Ingelman-Sundberg M. Hormone- and substrate-regulated intracellular degradation of cytochrome P450 (2E1) involving MgATP-activated rapid proteolysis in the endoplasmic reticulum membranes. J Biol Chem. 1992;267(22):15765-9.
[113] Rogers S, Wells R, Rechsteiner M. Amino acid sequences common to rapidly degraded proteins: the PEST hypothesis. Science. 1986;234(4774):364-8.
[114] Oesch-Bartlomowicz B, Padma PR, Becker R, Richter B, Hengstler JG, Freeman JE, Wolf CR, Oesch F. Differential modulation of CYP2E1 activity by cAMP-dependent protein kinase upon Ser129 replacement. Exp Cell Res. 1998;242(1):294-302.
[115] Zhukov A, Werlinder V, Ingelman-Sundberg M. Purification and characterization of two membrane bound serine proteinases from rat liver microsomes active in degradation of cytochrome P450. Biochem Biophys Res Commun. 1993;197(1):221-8.
[116] Wang HF, Figueiredo Pereira ME, Correia MA. Cytochrome P450 3A degradation in isolated rat hepatocytes: 26S proteasome inhibitors as probes. Arch Biochem Biophys. 1999;365(1):45-53.
[117] Fisher EA, Zhou M, Mitchell DM, Wu X, Omura S, Wang H, Goldberg AL, Ginsberg HN. The degradation of apolipoprotein B100 is mediated by the ubiquitin-proteasome pathway and involves heat shock protein 70. J Biol Chem. 1997;272(33):20427-34.
[118] Huan JY, Streicher JM, Bleyle LA, Koop DR. Proteasome-dependent degradation of cytochromes P450 2E1 and 2B1 expressed in tetracycline-regulated HeLa cells. Toxicol Appl Pharmacol. 2004;199(3):332-43.
[119] Bardag-Gorce F, Li J, French BA, French SW. Ethanol withdrawal induced CYP2E1 degradation in vivo, blocked by proteasomal inhibitor PS-341. Free Radic Biol Med. 2002;32(1):17-21.
[120] Hayes SA, Dice JF. Roles of molecular chaperones in protein degradation. J Cell Biol. 1996;132(3):255-8.