Both cytochromes P450 2E1 and 3A are involved in the O-hydroxylation of p-nitrophenol, a catalytic activity known to be specific for P450 2E1

Chemical Research in Toxicology

Volumn 10, Issue 10, 1997, Pages 1205-1212

  Zerilli, Alain ^a   Ratanasavanh, Damrong ^a   Lucas, Danièle ^a   Goasduff, Thierry ^a   Dréano, Yvonne ^a   Menard, Christophe ^a   Picart, Daniel ^a   Berthou, François ^a  

^a FACULTÉ DE MÉDECINE ET DES SCIENCES DE LA SANTÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

4 NITROCATECHOL; 4 NITROPHENOL; CYTOCHROME P450 INHIBITOR; CYTOCHROME P450 ISOENZYME; DEXAMETHASONE; DIETHYLDITHIOCARBAMIC ACID; KETOCONAZOLE; PYRAZOLE; TROLEANDOMYCIN;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CATALYSIS; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME INDUCTION; ENZYME INHIBITION; ENZYME KINETICS; ENZYME SPECIFICITY; HUMAN; HUMAN TISSUE; HYDROXYLATION; LIVER CELL CULTURE; LIVER MICROSOME; MALE; NONHUMAN; PROTEIN EXPRESSION; RAT;

ANIMALS; ARYL HYDROCARBON HYDROXYLASES; CELLS, CULTURED; CYTOCHROME P-450 CYP2E1; CYTOCHROME P-450 CYP3A; CYTOCHROME P-450 ENZYME SYSTEM; HUMANS; HYDROXYLATION; KINETICS; LIVER; MALE; MICROSOMES, LIVER; NITROPHENOLS; OXIDOREDUCTASES, N-DEMETHYLATING; RATS; RATS, WISTAR; SUBSTRATE SPECIFICITY;

EID: 0030830029     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx970048z     Document Type: Article

References (46)

1. Koop, D. R. (1992) Oxidative and reductive metabolism by cytochrome P450 2E1. FASEB J. 6, 724-730.
2. Guengerich, F. P., Kim, D. H., and Iwasaki, M. (1991) Role of human cytochrome P450 2E1 in the oxidation of many low molecular weight cancer suspects. Chem. Res. Toxicol. 4, 168-179.
3. Cederbaum, A. I. (1989) Role of lipid peroxidation and oxidative stress in alcohol toxicity. Free Radical Biol. Med. 7, 537-539.
4. Peter, R., Böcker, R., Beaune, P. H., Iwasaki, M., Guengerich, F. P., and Yang, C. S. (1990) Hydroxylation of chlorzoxazone as a specific probe for human liver cytochrome P450 2E1. Chem. Res. Toxicol. 3, 566-573.
5. Koop, D. R. (1986) Hydroxylation of p-nitrophenol by rabbit ethanol-inducible cytochrome P450 isozyme 3A. Mol. Pharmacol. 29, 399-404.
6. Jayyosi, Z., Knoble, D., Mac, M., Thomas, P. E., and Kelley, M. (1995) Cytochrome P450 2E1 is not the sole catalyst of chlorzoxazone hydroxylation in rat liver. J. Pharmacol. Exp. Ther. 273, 1156-1161.
7. Carrière, V., Goasduff, T., Ratanasavanh, D., Morel, F., Gautier, J. C., Guillouzo, A., Beaune, P., and Berthou, F. (1993) Both cytochrome P450 2E1 and 1A1 are involved in the metabolism of chlorzoxazone. Chem. Res. Toxicol. 6, 852-857.
8. Ono, S., Hatanaka, T., Hotta, H., Tsutsui, M., Satoh, T., and Gonzalez, F. J. (1995) Chlorzoxazone is metabolized by human CYP1A2 as well by human CYP2E1. Pharmacogenetics 5, 143-150.
9. Gorski, J. C., Jones, D. R., Wrighton, S. A., and Hall, S. D. (1997) Contribution of human CYP3A subfamily members to the 6-hydroxylation of chlorzoxazone. Xenobiotica 27, 243-256.
10. Girre, C., Lucas, D., Hispard, E., Ménez, C., Dally, S., and Ménez, J. F. (1994) Assessment of cytochrome P450 2E1 induction in alcoholic patients by chlorzoxazone pharmocokinetics. Biochem. Pharmacol. 47, 1503-1508.
11. Lucas, D., Ménez, J. F., and Berthou, F. (1996) Chlorzoxazone in-vitro and in-vivo substrate probe for liver CYP 2E1. In Methods in Enzymology, Cytochrome P450 (Johnson, E. F., and Waterman, M. R., Eds.) Vol. 272, pp 115-123, Academic Press, Orlando, FL.
12. Dicker, E., Mc Huge, T., and Cederbaum, A. I. (1990) Increased oxidation of p-nitrophenol and aniline by intact hepatocytes isolated from pyrazole-treated rats. Biochem. Biophys. Acta. 1035, 249-256.
13. Tassaneeyakul, W., Veronese, M. E., Birkett, D. J., Gonzalez, F. J., and Miners, J. O. (1993) Validation of 4-nitrophenol as in-vitro substrate probe for human liver CYP2E1 using cDNA expression and microsomal kinetic techniques. Biochem. Pharmacol. 46, 1975-1981.
14. Liu, C., Zhuo, X., Gonzalez, F. J., and Ding, X. (1996) Baculovirus-mediated expression and characterization of rat CYP2A3 and human CYP2A6: role in metabolic activation of nasal toxicants. Mol. Pharmacol. 50, 781-788.
15. Berthou, F., Ratanasavanh, D., Riché, C., Picart, D., Voirin, T., and Guillouzo, A. (1989) Comparison of caffeine metabolism by slices, microsomes and hepatocyte culture from adult human liver. Xenobiotica 19, 401-417.
16. Guguen-Guillouzo, C., and Guillouzo, A. (1986) Methods for preparation of adult and fetal hepatocytes. In Isolated and Cultured Hepatocytes (Guillouzo, A., and Guguen-Guillouzo, C., Eds.) pp 1-12, John Libbey Eurotext, London.
17. Berthou, F., Dréano, Y., Belloc, C., Kangas, L., Gautier, J. C., and Beaune, P. (1994) Involvement of cytochrome P450 3A enzyme family in the major metabolic pathways of toremifene in human liver microsomes. Biochem. Pharmacol. 47, 1883-1895.
18. Iribarne, C., Berthou, F., Baird, S., Dréano, Y., Picart, D., Bail, J. P., Beaune, P., and Ménez, J. F. (1996) Involvement of cytochrome P450 3A4 in the N-demethylation of methadone in human liver microsomes. Chem. Res. Toxicol. 9, 365-373.
19. Iribarne, C., Picart, D., Dréano, Y., Bail, J. P., and Berthou, F. (1997) Involvement of cytochrome P450 3A4 in the N-dealkylation of buprenorphine in human liver microsomes. Life Sci. 60, 1953-1964.
20. Tassaneeyakul, W., Veronese, M. E., Birkett, D. J., and Miners, J. O. (1993) High performance liquid chromatography assay for 4-nitrophenol hydroxylation, a putative cytochrome P450 2E1 activity in human liver microsomes. J. Chromatogr. 616, 73-78.
21. Mishin, V. M., Koinisto, T., and Lieber, C. S. (1996) The determination of cytochrome P450 2E1-dependent p-nitrophenol hydroxylation by HPLC with electrochemical detection. Anal. Biochem. 233, 212-215.
22. Guengerich, F. P., Martin, M. V., Beaune, P. H., Kremers, P., Wolf, T., and Waxman, D. J. (1986) Characterization of rat and human microsomal cytochrome P450 forms involved in nifedipine oxidation, a prototype for genetic polymorphism in oxidative drug metabolism. J. Biol. Chem. 261, 5051-5060.
23. Rodrigues, A. D. (1994) Use of in-vitro human metabolism studies in drug development. Biochem. Pharmacol. 48, 2147-2156.
24. Bourrié, M., Meunier, V., Berger, Y., and Fabre, G. (1996) Cytochrome P450 isoform inhibitors as a tool for the investigation of metabolic reactions catalyzed by human liver microsomes. J. Pharmacol. Exp. Ther. 277, 321-332.
25. Song, B. J., Matsunaga, T., Hardwick, J. P., Park, S. S., Veech, R. L., Yang, C. S., Gelboin, H. V., and Gonzalez, F. J. (1987) Stabilization of cytochrome P450j messenger RNA in the diabetic rat. Mol. Endocrinol. 1, 542-547.
26. Chomczynski, P., and Saachi, N. (1987) Simple step method of RNA isolation by acid guanidium thiocyanate phenol chloroform extraction. Anal. Biochem. 162, 156-159.
27. Saarinen, J., Saarelainen, R., and Lindros, K. O. (1993) A rapid method to study heterogeneous gene expression in liver by direct assay of messenger RNA from periportal and perivenous cell lysates. Hepatology 17, 466-469.
28. Morris, D. L., and Davila, J. C. (1996) Analysis of rat cytochrome P450 isoenzyme expression using semi-quantitative reverse transcriptase-polymerase chain reaction (RT-PCR). Pharmacology 52, 181-7892.
29. Babany, G., Larrey, D., and Pessayre, D. (1988) Macrolide antibiotics as inducers and inhibitors of cytochrome P450 in experimental animal and man. In Progress in Drug Metabolism (Gibson, G. G., Ed.) pp 61-98, Taylor and Francis, London.
30. Namkung, G., Yang, H. L., Hulla, J. E., and Juchau, M. R. (1988) On the substrate specificity of cytochrome P450 3A1. Mol. Pharmacol. 34, 628-637.
31. Cooper, K. O., Reik, L. M., Jayyosi, Z., Bandiera, S., Kelly, M., Ryan, D. E., Daniel, R., McCluskey, S. A., Levin, W., and Thomas, P. E. (1993) Regulation of two members of the steroid-inducible cytochrome P450 subfamily (3A) in rats. Arch. Biochem. Biophys. 301, 345-354.
32. Gonzalez, F. J., Song, B. J., and Hardwick, J. P. (1986) Pregnenolone 16α-carbonitrile-inducible P450 gene family: gene conversion and differential regulation. Mol. Cell. Biol. 6, 2969-2976.
33. Zerilli, A., Lucas, D., Dréano, Y., Picart, D., and Berthou, F. (1997) Effect of pyrazole and dexamethasone administration on the expression of P450 2E1 and 3A isoforms in rat liver and kidney. Submitted for publication.
34. Veng, Y. F., Kuwabara, T., Chun, Y. J., and Guengerich, F. P. (1997) Cooperativity in oxidations catalyzed by P450 3A4. Biochemistry 36, 370-381.
35. Goasduff, T., Bellec, G., Amet, Y., Dréano, Y., Ménez, J. F., and Berthou, F. (1996) P450 2E1 expression in liver, kidney, and lung of rats treated with single or combined inducers. Alcohol 13, 301-308.
36. Goasduff, T., Ménez, J. F., Dréano, Y., and Berthou, F. (1995) CYP1A2 and 2E1 expression in rat liver treated with combined inducers (3-methylcholanthrene and ethanol). Biochem. Biophys. Res. Commun. 211, 497-503.
37. Chen, W., Peter, R. M., McArdle, S., Thunnel, K. E., Sigle, R. O., and Nelson, S. D. (1996) Baculovirus expression and purification of human and rat cytochrome P450 2E1. Arch. Biochem. Biophys. 335, 123-130.
38. 5: spectral and catalytic properties and effect of 65 on the stoichiometry of P450 2E1-catalyzed reactions. Arch. Biochem. Biophys. 317, 504-513.
39. Mapoles, J., Berthou, F., Alexander, A., Simon, F., and Ménez, J. F. (1993) Mammalian PC-12 cell genetically engineered for human cytochrome P450 2E1 expression. Eur. J. Biochem. 214, 735-745.
40. Renaud, J. P., Cullin, C., Pompon, D., Beaune, P., and Mansay, D. (1990) Expression of human liver cytochrome P450 3A4 in yeast. Eur. J. Biochem. 194, 889-896.
41. Gillam, E. M. J., Baba, T., Kim, B. K., Ohmori, S., and Guengerich, F. P. (1993) Expression of modified human cytochrome P450 3A4 in Escherichia coli and purification and reconstitution of the enzyme. Arch. Biochem. Biophys. 305, 123-131.
42. Lee, C. A., Kadwell, S. H., Kost, T. A., and Serabjit-Singh, C. J. (1995) CYP3A4 expressed by insect cells infected with a recombinant baculovirus containing both CYP3A4 and human NADPH-cytochrome P450 reductase is catalytically similar to human liver microsomal CYP3A4. Arch. Biochem. Biophys. 319, 157-167.
43. Peyronneau, M. A., Renaud, J. P., Truan, G., Urban, P., Pompon, D., and Mansuy, D. (1992) Optimization of yeast-expressed human liver cytochrome P450 3A4 catalytic activities by expressing NADPH-P450 reductase and cytochrome b5. Eur. J. Biochem. 207, 109-116.
44. Gillan, E. M. J., Guo, Z., Ueng, Y. F., Yamazaki, H., Cock, I., Reilly, P. E. B., Hooper, W. D., and Guengerich, F. P. (1995) Expression of cytochrome P450 3A5 in Escherichia coli: effect of 5′ modification, purification, spectral characterization, reconstitution conditions and catalytic activities. Arch. Biochem. Biophys. 317, 374-384.
45. Guengerich, F. P., and Turvy, C. G. (1991) Comparison of levels of several human microsomal cytochrome P450 enzymes and epoxide hydroxylase in normal and diseases state using immunochemical analysis of surgical liver samples. J. Pharmacol. Exp. Ther. 256, 1189-1194.
46. Belloc, C., Baird, S., Lecoeur, S., Cosme, J., Gautier, J. C., de Waziers, I., Flinois, J. P., and Beaune, P. H. (1996) Human cytochromes P450 expressed in Escherichia coli: production of specific antibodies. Toxicology 106, 207-219.