Metabolism of benzene in human liver microsomes: Individual variations in relation to CYP2E1 expression

Archives of Toxicology

Volumn 73, Issue 1, 1999, Pages 33-40

  Nedelcheva, Vessela ^a   Gut, Ivan ^a   Souček, Pavel ^a   Tichavská, Bronislava ^a   Týnkova, Lucie ^a   Mráz, Jaroslav ^a   Guengerich, F Peter ^b   Ingelman Sundberg, Magnus ^c  

^a NATIONAL INSTITUTE OF PUBLIC HEALTH   (Czech Republic)

^b VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

^c KAROLINSKA INSTITUTE   (Sweden)

Author keywords

Benzene Chlorzoxazone; Covalent binding; Cytochrome P450; Enzyme kinetics

Indexed keywords

4 NITROPHENOL; ANILINE; BENZENE; CHLORZOXAZONE; CYTOCHROME P450; N,N DIMETHYLFORMAMIDE;

ARTICLE; DRUG METABOLISM; DRUG PROTEIN BINDING; ENZYME ACTIVITY; ENZYME INDUCTION; HUMAN; HUMAN TISSUE; LIVER MICROSOME METABOLISM; MICHAELIS CONSTANT; PRIORITY JOURNAL;

BENZENE; CARBON RADIOISOTOPES; CHELATING AGENTS; CYTOCHROME P-450 CYP2E1; DITIOCARB; GENOTYPE; GLUTATHIONE; HUMANS; IMMUNOBLOTTING; KINETICS; METHANE; MICROSOMES, LIVER; OXIDATION-REDUCTION; SOLUBILITY; SUBSTRATE SPECIFICITY; WATER;

EID: 0032892913     PISSN: 03405761     EISSN: None     Source Type: Journal    
DOI: 10.1007/s002040050583     Document Type: Article

References (48)

1. Carriere V, Goasduff T, Ratanasavanh D, Morel F, Gautier JC, Guillouzo A, Beaune P, Berthou F (1993) Both cytochromes P450 2E1 and 1A1 are involved in the metabolism of chlorzoxazone. Chem Res Toxicol 6: 852-878
2. Ekström G, Ingelman-Sundberg M (1989) Human liver cytochrome P450IIE1. Immunological evaluation of its contribution to microsomal ethanol oxidation, carbon tetrachloride reduction and NADPH oxidase activity. Biochem Pharmacol 38: 689-693
3. Eliasson E, Johansson I, Ingelman-Sundberg M (1990) Substrate-, hormone-, and cAMP-regulated cytochrome P450 degradation. Proc Natl Acad Sci USA 87: 3225-3227
4. Girre C, Lucas D, Hispard E, Menez C, Dally S, Menez J-F (1994) Assessment of cytochrome P4502E1 induction in alcoholic patients by chlorzoxazone pharmacokinetics. Biochem Pharmacol 47: 1503-1508
5. Gram TE, Rogers LA, Fouts JR (1967) Further studies on the metabolism of drugs by subfractions of hepatic microsomes. J Pharmacol Exp Ther 150: 479-493
6. Greenlee WF, Sun JD, Bus JS (1981) A proposed mechanism of benzene toxicity: formation of reactive intermediates from polyphenol metabolites. Toxicol Appl Pharmacol 59: 187-195
7. Guengerich FP, Martin M, Beaune PH, Kremers P, Wolf T, Waxman D (1986) Characterization of rat and human microsomal P450 forms involved in the nifedipine oxidation - a prototype for genetic polymorphysm in oxidative drug metabolism. J Biol Chem 261: 5051-5060
8. Guengerich FP, Kim D-H, Iwasaki M (1991) Role of human P450 IIE1 in the oxidation of many low molecular weight cancer suspects. Chem Res Toxicol 4: 168-178
9. Guengerich FP, Bell LC, Okazaki O (1995) Interpretations of cytochrome P450 mechanisms from kinetic studies. Biochimie 77: 573-580
10. Gut I, Terelius Y, Frantík E, Linhart I, Souček P, Filipcová B, Klučková H (1993) Exposure to various benzene derivatives differently induces cytochromes P450 2B1 and P450 2E1 in rat liver. Arch Toxicol 67: 237-243
11. Gut I, Nedelcheva V, Souček P, Vodička P, Gelboin HV, Ingelman-Sundberg M (1996) The role of CYP2E1 and 2B1 in metabolic activation of benzene. Arch Toxicol 71: 45-56
12. Hirvonen A, Husgafvel-Pursiainen K, Anttila S, Karjalainen A, Vainio H (1993) The human CYP2E1 gene and lung cancer: DraI and RsaI restriction fragment polymorphism in a Finnish study population. Carcinogenesis 14: 85-88
13. Hyland R, Gescher A, Thummel K, Schiller C, Jheeta P, Mynett K, Smith AW, Mraz J (1991) Metabolic oxidation and toxification of N-methylformamide is catalyzed by the cytochrome P450 isoenzyme CYP2E1. Mol Pharmacol 41: 259-266
14. IARC monographs on the evaluation of carcinogenic risk to humans (1987) An updating of IARC monographs vol 1-42, Suppl 7. International Agency for Research on Cancer. Lyon , France
15. Ingelman-Sundberg M, Johansson I, Terelius Y, Eliasson F, Ekström G, Buhler R, Londros KO (1993) Ethanol-inducible CYP2E1: toxicological importance and regulation by nutrients. In: (Parke DV, Ioannides C, Walker R (eds) Food, nutrition and chemical toxicity. Smith-Gordon, Great Britain, pp 147-160
16. Irons RD (1985) Quinones as toxic metabolites of benzene. J Toxicol Environ Health 16: 673-8
17. Johansson I, Ingelman-Sundberg M (1983) Hydroxyl radical-mediated, cytochrome P-450-dependent metabolic activation of benzene in microsomes and reconstituted enzyme systems from rabbit liver. J Biol Chem 258: 7311-7316
18. Johansson I, Ekström G, Scholte B, Puzycki D, Jörnvall H, Ingelman-Sundberg M (1988) Ethanol-, fasting-, and acetone-inducible cytochrome P-450 in rat liver: regulation and characteristics of enzymes belonging to the IIB and IIE gene subfamilies. Biochemistry 27: 1925-1934
19. Knodell RG, Hall SD, Wilkinson GR, Guengerich FP (1987) Hepatic metabolism of tolbutamide: characterization of the form of cytochrome P450 involved in methyl-hydroxylation and relationship to in vivo disposition. J Pharmacol Exp Ther 241: 1112-1119
20. Koop DR, Laethem CL, Schnier GG (1989) Identification of ethanol inducible P450 isozyme 3a (P450IIE1) as benzene and phenol hydroxylase. Toxicol Appl Pharmacol 98: 278-288
21. 4. Nature 227: 680-685
22. Lowry OH, Rosebrough NJ, Farr AL, Randall RJ (1951) Protein measurement with the Folin phenol reagent. J. Biol Chem 193: 265-275
23. Labet RA, Mayer RT, Cameron JW, Nims RW, Burke MD, Wolf T, Guengerich FP (1985) Dealkylation of penthoxyresorufin: a rapid and sensitive assay for measuring induction of cytochromes P450 by phenobarbital and other xenobiotics in the rat. Arch Biochem Biophys 283: 43-48
24. Lucas D, Berthou F, Dreano Y, Lozach P, Volant A, Menez J-F (1993) Comparison of levels of cytochrome P-450, CYP1A2, CYP2E1, and their related monooxygenase activities in human surgical liver samples. Alcohol Clin Exp 17: 900-905
25. Lucas D, Menez C, Girre C, Berthou F, Bodenez P, Joannet I, Hispard E, Bardou L-G, Menez J-F (1995) Cytochrome P450 2E1 genotype and chlorzoxazone metabolism in healthy and alcoholic Caucasian subjects. Pharmacogenetics 5: 298-304
26. Mraz J, Jheeta P, Gescher A, Hyland R, Thummel K, Treadgill MD (1993) Investigation of the mechanistic basis of N,N-dimethylformamide toxicity. Metabolism of N,N-dimethylformamide and its deuterated isotopomers by cytochrome P4502E1. Chem Res Toxicol 6: 197-207
27. Nakajima T, Okuyama S, Yonekura I, Sato A (1985) Effects of ethanol and phenobarbital administration on the metabolism and toxicity of benzene. Chem-Biol Interact 55: 23-38
28. Nakajima T, Wang R-S, Elovaara E, Park SS, Gelboin HV, Vainio H (1992) A comparative study on the contribution of cytochrome P450 isozymes to metabolism of benzene, toluene and trichloroethylene in rat liver. Biochem Pharmacol 43: 251-257
29. Nedelcheva V, Gut I (1994) Cytochrome P450 in rats and humans: methods of investigation, substrate specificities and relevance to cancer. Xenobiotica 24: 1151-1175
30. Nedelcheva V, Persson I, Ingelman-Sundberg M (1996) Genetic polymorphism of human cytochrome P450 2E1. Methods Enzymol 272: 218-225
31. Nelson DR, Koymans L, Kamataki T, Stegeman JJ, Feyereisen R, Waxman DJ, Waterman MR, Gotoh O, Coon MJ, Estabrook RW, Gunsalus IC, Nebert DW (1996) P450 superfamily: update of new sequences, gene mapping, accession number and nomenclature. Pharmacogenetics 6: 1-42
32. Omura T, Sato R (1964) The carbon-monoxide-binding pigment of liver microsomes. II. Solubilization, purification, properties. J Biol Chem 239: 2379-2385
33. Perrot N, Nalpas B, Yang CS, Beaune PH (1989) Modulation of cytochrome P450 isozymes in human liver by ethanol and alcohol intake. Eur J Clin Invest 19: 545-555
34. Persson I, Johansson I, Bergling H, Dahl M-L, Seidegard J, Rylander R, Rannug A, Hogberg J, Ingelman Sundberg M (1993) Genetic polymorphism of cytochrome P4502E1 in a Swedish population. Relationship to incidence of lung cancer. FEBS Lett 319: 207-211
35. Peter R, Böcker R, Beaune PH, Iwasaki M, Guengerich FP, Yang CS (1990) Hydroxylation of chlorzoxazone as a specific probe for human liver cytochrome P450IIE1. Chem Res Toxicol 3: 566-573
36. Reinke LA, Moyer MJ (1985) p-Nitrophenol hydroxylation A microsomal oxidation which is highly inducible by ethanol. Drug Metab Dispos 13: 548-573
37. Schlosser PM, Bond JA, Medinski MA (1993) Benzene and phenol metabolism by mouse and rat liver. Carcinogenesis 14: 2477-2486
38. Seaton MJ, Schlosser PM, Bond JA, Medinsky MA (1994) Benzene metabolism by human liver microsomes in relation to cytochrome P4502E1 activity. Carcinogenesis 15: 1799-1806
39. Smith MT, Yager JW, Steinmetz KL, Eastmond DA (1989) Peroxidase-dependent metabolism of benzene's phenolic metabolites and its potential role in benzene toxicity and carcinogenicity. Environ Health Perspect 82: 23-29
40. Souček P, Filipcova B, Gut I (1994) Cytochrome P450 destruction and radical scavenging by benzene and its metabolites. Evidence for the key role of quinones. Biochem Pharmacol 47: 2233-2242
41. Tassaneeyakul W, Veronese ME, Birkett DJ, Miners JO (1993) High-performance liquid Chromatographic assay for 4-nitrophenol hydroxylation, a putative cytochrome P-4502E1 activity, in human liver microsomes. J Chromatogr 616: 73-78
42. Tindberg N, Ingelman-Sundberg M (1989) Cytochrome P-450 and oxygen toxicity. Oxygen-dependent induction of ethanol-inducible cytochrome P-450 in rat liver and lung. Biochemistry 28: 4449-4504
43. Towbin H, Staehelin T, Gordon J (1979) Electrophoretic transfer of proteins from polyacrylamide gels to nitrocellulose sheets: procedure and some applications. Proc Natl Acad Sci USA 76: 4350-4356
44. Uematsu F, Kikuchi H, Motomiya M, Abe T, Ishioka C, Kanamaru R, Sagami I, Watanabe M (1992) Human cytochromes P450IIE1 gene: DraI polymorphism and susceptibility to cancer. Tohoku J Exp Med 168: 113-117
45. Valentine JL, Lee SS-T, Seaton MJ, Asgharian B, Farris G, Corton JC, Gonzalez FJ, Medinsky MA (1996) Reduction of benzene metabolism and toxicity in mice that lack CYP2E1 expression. Toxicol Appl Pharmacol 141: 205-213
46. Yamazaki H, Guo Z, Guengerich FP (1995) Selectivity of cytochrome P450 2E1 chlorzoxazone 6-hydroxylation. Drug Metab Dispos 23: 438-440
47. Yang CS Ishizaki H, Lee MJ, Wade D, Fadel A (1991) Deuterium isotope effect in the interaction of N-nitrosodimethylamine, ethanol, and related compounds with cytochrome P450IIE1. Chem Res Toxicol 4: 408-413
48. Yin SN (1995) A cohort study of cancer among benzene-exposed workers in China. (Abstract) Benzene '95: International Conference on the Toxicity, Carcinogenesis and Epidemiology of Benzene, June 17-20. EOHSI, Environmental and Occupational Health Sciences Institute, Piscataway, New Jersey, USA