Involvement of cytochrome P450, glutathione S-transferase, and epoxide hydrolase in the metabolism of aflatoxin B1 and relevance to risk of human liver cancer

Environmental Health Perspectives

Volumn 104, Issue SUPPL. 3, 1996, Pages 557-562

  Guengerich, F Peter ^a   Johnson, William W ^a   Ueng, Yune Fang ^a   Yamazaki, Hiroshi ^b   Shimada, Tsutomu ^b  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b OSAKA PREFECTURAL INSTITUTE OF PUBLIC HEALTH   (Japan)

Author keywords

Aflatoxin B1; Cytochrome P450; Epoxide hydrolase; Glutathione; Glutathione S transferase; Metabolism of chemical carcinogens; Metabolism of mycotoxins

Indexed keywords

AFLATOXIN B1; CYTOCHROME P450; EPOXIDE HYDROLASE; GLUTATHIONE TRANSFERASE;

CANCER RISK; CONFERENCE PAPER; GENOTOXICITY; HUMAN; KINETICS; LIVER CANCER; LIVER CARCINOGENESIS; LIVER METABOLISM; PRIORITY JOURNAL; SMALL INTESTINE;

EID: 0029976725     PISSN: 00916765     EISSN: None     Source Type: Journal    
DOI: 10.1289/ehp.96104s3557     Document Type: Conference Paper

References (55)

1. Mueller GC, Miller JA. The metabolism of 4-dimethylaminoazobenzene by rat liver homogenstes. J Biol Chem 176:535-544 (1948).
2. Guengerich FP. Metabolic activation of carcinogens. Pharmacol Ther 54:17-61 (1992).
3. Conney AH, Miller EC, Miller JA. The metabolism of methylated aminoazo dyes. V. Evidence for induction of enzyme synthesis in the rat by 3-methylcholanthrene. Cancer Res 16:450-459 (1956).
4. Nebert DW. The Ah locus: genetic differences in toxicity, cancer, mutation, and birth defects. Crit Rev Toxicol 20:153-174 (1989).
5. Boberg EW, Liem A, Miller EC, Miller JA. Inhibition by pentachlorophenol of the initiating and promoting activites of 1′-hydroxysafrole for the formation or enzyme-altered foci and tumors in rat liver. Carcinogenesis 8:531-539 (1987).
6. Bolton MG, Mufioz A, Jacobson LP, Groopman JD, Maxuitenko YY, Roebuck BD, Kensler TW. Transient intervention with oltipraz protects against aflatoxin-induced hepatic tumorigenesis. Cancer Res 53:3499-3504 (1993).
7. Guengerich FP. Roles of cytochrome P-450 enzymes in chemical carcinogenesis and cancer chemotherapy. Cancer Res 48:2946-2954 (1988).
8. Guengerich FP, Shimada T. Oxidation of toxic and carcinogenic chemicals by human cytochrome P-450 enzymes. Chem Res Toxicol 4:391-407 (1991).
9. Shimada T, Iwasaki M, Martin MV, Guengerich FP. Human liver microsomal cytochrome P-450 enzymes involved in the bioactivation of procarcinogens detected by umu gene response in Salmonella typhimurium TA1535/pSK1002. Cancer Res 49:3218-3228 (1989).
10. Guengerich FP, Shimada T. Human cytochrome P-450 enzymes and chemical carcinogenesis. In: Human Drug Metabolism: From Molecular Biology to Man (Jeffrey EH, ed). Boca Raton, FL:CRC Press, 1993;5-12.
11. Guengerich FP. Human cytochrome P450 enzymes. In: Cytochrome P450 (Ortiz de Montellano PR, ed). New York:Plenum Press, 1995;473-535.
12. Ayesh R, Idle JR, Ritchie JC, Crothers MJ, Hetzel MR. Metabolic oxidation phenotypes as markers for susceptibility to lung cancer. Nature 312:169-170 (1984).
13. Drakoulis N, Minks T, Ploch M, Otte F, Heinemeyer G, Kampf D, Loddenkemper R, Roots I. Questionable association of debrisoquine hydroxilator phenotype and risk for bronchial carcinoma. Acta Pharmacol Toxicol 59(Supp 5):220 (1986).
14. Daly AK, Cholerton S, Armstrong M, Idle JR. Genotyping for polymorphisms in xenobiotic metabolism as a predictor of disease susceptibility. Environ Health Perspect 102(Suppl 9):55-61 (1994).
15. Boobis AR, Davies DS. Debrisoquine oxidation phenotype and susceptibility to lung cancer. Br J Clin Pharmacol 30:653-656 (1990).
16. Wolff T, Distlerath LM, Worthington MT, Groopman JD, Hammons GJ, Kadlubar FF, Prough RA, Martin MV, Guengerich FP. Substrate specificity of human liver cytochrome P-450 debrisoquine 4-hydroxylase probed using immunochemical inhibition and chemical modeling. Cancer Res 45:2116-2122 (1985).
17. Shimada T, Guengerich FP. Activation of amino-α-carboline, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine and a copper phthalocyanine cellulose extract of cigarette smoke conden-sate by cytochrome P-450 enzymes in rat and human liver microsomes. Cancer Res 51:5284-5291 (1991).
18. Crespi CL, Penman BW, Gelboin HV, Gonzalez FJ. A tobacco smoke-derived nitrosamine, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, is activated by multiple human cytochrome P450s including the polymorphic human cytochrome P4502D6. Carcinogenesis 12:1197-1201 (1991).
19. Busby WF, Wogan GN. Aflatoxins. In: Chemical Carcinogens (Searle CE, ed). Washington:American Chemical Society, 1984;945-1136.
20. Wogan GN. Aflatoxins as risk factors for hepatocellular carcinoma in humans. Cancer Res 52(Suppl 7):2114s-2118s (1992).
21. 1 in vitro. Proc Natl Acad Sci USA 74:1870-1874 (1977).
22. 1-DNA or -ribosomal RNA adducts formed in hepatic microsome-mediated reactions and in rat liver in vivo. Cancer Res 37:4430-4438 (1977).
23. 1: the ultimate carcinogenic species. J Am Chem Soc 110:7929-7931 (1988).
24. Raney KD, Coles B, Guengerich FP, Harris TM. The endo 8,9-epoxide of aflatoxin B1: a new metabolite. Chem Res Toxicol 5:333-335 (1992).
25. 1 exo and endo epoxides by rat and human glutathione S-transferases. Chem Res Toxicol 5:470-478 (1992).
26. Sandhu P, Guo Z, Baba T, Martin MV, Tukey RH, Guengerich FP. Expression of modified human cytochrome P450 1A2 in Escherichia coli: stabilization, purification, spectral characterization, and catalytic activities of the enzyme. Arch Biochem Biophys 309:168-177 (1994).
27. Gillam EMJ, Baba T, Kim B-R, Ohmori S, Guengerich FP. Expression of modified human cytochrome P450 3A4 in Escherichia coli and purification and reconstitution of the enzyme. Arch Biochem Biophys 305:123-131 (1993).
28. Yasukochi Y, Masters BSS. Some properties of a detergent-solubilized NADPH-cytochrome c (cytochrome P-450) reductase purified by biospecific affinity chromatography. J Biol Chem 251:5337-5344 (1976).
29. Funae Y, Imaoka S. Simultaneous purification of multiple forms of rat liver microsomal cytochrome P-450 by high-performance liquid chromatography. Biochim Biophys Acta 842:119-132 (1985).
30. Guengerich FP, Wang P, Mitchell MB, Mason PS. Rat and human liver microsomal epoxide hydratase. Purification and evidence for the existence of multiple forms. J Biol Chem 254:12248-12254 (1979).
31. 1 by bacterial recombinant human cytochrome P450 enzymes. Chem Res Toxicol 8:218-225 (1995).
32. Shimada T, Oda Y, Yamazaki H, Mimura M, Guengerich FP. SOS function tests for studies of chemical carcinogenesis in Salmonella typhimurium TA 1535/pSK1002, NM2009, and NM3009. In: Methods in Molecular Genetics. Vol 5 (Adolph KW, ed). Orlando, FL:Academic Press, 1994;342-355.
33. Barshop BA, Wrenn RF, Frieden C. Analysis of numerical methods for computer simulation of kinetic processes: development of KINSIM - a flexible, portable system. Anal Biochem 130:134-145 (1983).
34. NF, the nifedipine oxidase, being the principal enzyme involved in the bioactivation of aflatoxins in human liver. Proc Natl Acad Sci USA 86:462-465 (1989).
35. 1. Proc Natl Acad Sci USA 87:4790-4793 (1990).
36. 1 metabolism in human liver. Proc Natl Acad Sci USA 87:8306-8310 (1990).
37. 1. Chem Res Toxicol 5:202-210 (1992).
38. Crespi CL, Penman BW, Leakey JAE, Arlotto MP, Stark A, Parkinson A, Turner T, Steimel DT, Rudo K, Davies RL, Langenbach R. Human cytochrome P450IIA3: cDNA sequence, role of the enzyme in the metabolic activation of promutagens, comparison to nitrosamine activation by human cytochrome P450IIE1. Carcinogenesis 11:1293-1300 (1990).
39. Yun C-H, Shimada T, Guengerich FP. Purification and characterization of human liver microsomal cytochrome P-450 2A6. Mol Pharmacol 40:679-685 (1991).
40. 1-4-hydroxylase. J Biol Chem 263:12187-12189 (1988).
41. 3-450 gene. J Biol Chem 263:12584-12595 (1988).
42. 1 to mutagens by human liver. Biochem Biophys Res Commun 82:348-355 (1978).
43. 1metabolism in human liver microsomes by naturally occurring flavonoids. Cancer Res 41:67-72 (1981).
44. Guengerich FP, Kim B-R, Gillam EMJ, Shimada T. Mechanisms of enhancement and inhibition of cytochrome P450 catalytic activity. In: Proceedings of the 8th International Conference on Cytochrome P450: Biochemistry, Biophysics, and Molecular Biology (Lechner MC, ed). Chichester, U.K.:John Libbey Eurotext, 1994;97-101.
45. 1-induced hepatocarcinogenesis in F344 rats by 5-(2-pyrazinyl)-4-methyl-1,2-dithiole-3-thione (oltipraz): predictive role for short-term molecular dosimetty. Cancer Res 51:5501-5506 (1991).
46. 1 mechanistic studies. J Am Chem Soc 116:1603-1609 (1994).
47. 7 adducts and inducing different genetic responses. Chem Res Toxicol 2:114-122 (1989).
48. 7 adducts by aflatoxin epoxides. Chem Res Toxicol 3:254-261 (1990).
49. 1. Proc Natl Acad Sci USA 92:2384-2387 (1995).
50. 1 in isolated rat hepatocytes. Biochem Biophys Res Commun 110:668-674 (1983).
51. 1 in vivo in rats. Carcinogenesis 8:819-824 (1987).
52. Hassett C, Aicher L, Sidhu JS, Omiecinski CJ. Human microsomal epoxide hydrolase: genetic polymorphism and functional expression in vitro of amino acid variants. Hum Mol Genet 3:421-428 (1994).
53. Liu YH, Taylor J, Linko P, Lucier GW, Thompson CL. Glutathione S-transferase μ in human lymphocyte and liver: role in modulating formation of carcinogen-derived DNA adducts. Carcinogenesis 12:2269-2275 (1991).
54. 1 metabolism in human hepatocytes in primary culture. Cancer Res 55:5574-5579 (1995).
55. Shimada T, Yamazaki H, Oda Y, Hiratsuka A, Watabe T, Guengerich FP. Activation and inactivation of carcinogenic dihaloalkanes and other compounds by glutathione S-transferase 5-5 in Salmonella typhimurium tester strain NM5004. Chem Res Toxicol 9:333-340 (1996).