Assessment of specificity of eight chemical inhibitors using cDNA-expressed cytochromes P450

Xenobiotica

Volumn 30, Issue 4, 2000, Pages 327-343

  Sai, Y ^a   Dai, R ^a   Yang, T J ^a   Krausz, K W ^a   Gonzalez, F J ^a   Gelboin, H V ^a   Shou, M ^b  

^a NATIONAL CANCER INSTITUTE   (United States)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

7 ETHOXYCOUMARIN; ALPHA NAPHTHOFLAVONE; CYTOCHROME P450; CYTOCHROME P450 2C9; CYTOCHROME P450 3A4; DIAZEPAM; DIETHYLDITHIOCARBAMIC ACID; DIMETHYLNITROSAMINE DEMETHYLASE; FURAFYLLINE; KETOCONAZOLE; ORPHENADRINE; PHENANTHRENE; QUINIDINE; SULFAPHENAZOLE; TESTOSTERONE;

ADULT; ARTICLE; DRUG INHIBITION; DRUG METABOLISM; DRUG SPECIFICITY; FEMALE; HUMAN; INHIBITION KINETICS; LIVER MICROSOME; MALE;

EID: 0034013033     PISSN: 00498254     EISSN: None     Source Type: Journal    
DOI: 10.1080/004982500237541     Document Type: Article

References (42)

1. Back, D. J., Tjia, J. F., Karbwang, J. and Colbert, J., 1988, In vitro inhibition studies of tolbutamide hydroxylase activity of human liver microsomes by azoles, sulphonamides and quinolines. British Journal Clinical Pharmacology, 26, 23-29.
2. Baldwin, S. J., Bloomer, J. C., Smith, G. J., Ayrton, A. D., Clarke, S. E., Chener, Y. and Henery, R. J., 1995, Ketoconazole and sulphaphenazole as the respective selective inhibitors of P4503A and 2C9. Xenobiotica, 25, 261-270.
3. Battula, N., Sagara, J. and Gelboin, H. V., 1987, Expression of P1-450 and P3-450 DNA coding sequences as enzymatically active cytochromes P-450 in mammalian cells. Proceedings of the National Academy of Sciences, USA, 84, 4073-4077.
4. Bonnabry, P., Leemann, T. and Dayer, P., 1996, Role of human liver microsomal CYP2C9 in the biotransformation of lornoxicam. European Journal of Clinical Pharmacology, 49, 305-308.
5. Bourrie, 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. Journal of Pharmacology and Experimental Therapeutics, 277, 321-332.
6. Chang, T. K., Gonzalez, F. J. and Waxman, D. J., 1994, Evaluation of triacetyloleandomycin, alpha-naphthoflavone and diethyldithiocarbamate as selective chemical probes for inhibition of human cytochromes P450. Archives of Biochemistry and Biophysics, 311, 437-442.
7. Chang, T. K., Weber, G. F., Crespi, C. L. and Waxman, D. J., 1993, Differential activation of cyclophosphamide and ifosphamide by cytochromes P-450 2B and 3A in human liver microsomes. Cancer Research, 53, 5629-5637.
8. Gelboin, H V. 1993, Cytochrome P450 and monoclonal antibodies. Pharmacological Review, 45, 413-453
9. Gelboin, H. V., Krausz, K. W., Goldfarb, I., Buters, J. T., Yang, S. K., Gonzalez, F. J., Korzekwa, K. R. and Shou, M., 1995, Inhibitory and non-inhibitory monoclonal antibodies to human cytochrome P450 3A3/4. Biochemical Pharmacology, 50, 1841-1850.
10. Gonzalez, F. J., Aoyama, T. and Gelboin, H. V., 1991a, Expression of mammalian cytochrome P450 using vaccinia virus. Methods Enzymology, 206, 85-92.
11. Gonzalez, F. J., Kimura, S., Tamura, S. and Gelboin, H. V., 1991b, Expression of mammalian cytochrome P450 using baculovirus. Methods Enzymology, 206, 93-99.
12. Gonzalez, F. J. and Korzekwa, K. R., 1995, Cytochromes P450 expression systems. Annual Review of Pharmacology and Toxicology, 35, 369-390.
13. Guengerich, F. P., Kim, D. H. and Iwasaki, M., 1991, Role of human cytochrome P-450 IIE1 in the oxidation of many low molecular weight cancer suspects. Chemical Research in Toxicology, 4, 168-179.
14. Halpert, J. R., Guengerich, F. P., Bend, J. R. and Correia, M. A. 1994, Selective inhibitors of cytochromes P450. Toxicology and Applied Pharmacology, 125, 163-175.
15. Hasegawa, T., Hara, K., Kenmochi, T. and Hata, S., 1994, In vitro metabolism of dorzolamide, a novel potent carbonic anhydrase inhibitor, in rat liver microsomes. Drug Metabolism and Disposition, 22, 916-921.
16. Heyn, H., White, R. B. and Stevens, J. C., 1996, Catalytic role of cytochrome P4502B6 in the N-demethylation of S-mephenytoin. Drug Metabolism and Disposition, 24, 948-954.
17. Johnson, E. F., Schwab, G. E. and Muller-Eberhard, U., 1979, Multiple forms of cytochrome P-450: catalytic differences exhibited by two homogeneous forms of rabbit cytochrome P-450. Molecular Pharmacology, 15, 708-718.
18. Kharasch, E. D. and Thummel, K. E., 1993, Identification of cytochrome P450 2E1 as the predominant enzyme catalyzing human liver microsomal defluorination of sevoflurane, isoflurane, and methoxyflurane. Anesthesiology, 79, 795-807.
19. Kunze, K. L. and Trager, W. F., 1993, Isoform-selective mechanism-based inhibition of human cytochrome P450 1A2 by furafylline. Chemical Research in Toxicology, 6, 649-656.
20. Lakshmi, V. M., Zenser, T. V. and Davis, B. B., 1997, Rat liver cytochrome P450 metabolism of N-acetylbenzidine and N,N′-diacetylbenzidine. Drug Metabolism and Disposition, 25, 481-488.
21. Lang, D. H., Rettie, A. E. and Bocker, R. H., 1997, Identification of enzymes involved in the metabolism of atrazine, terbuthylazine, ametryne, and terbutryne in human liver microsomes. Chemical Research in Toxicology, 10, 1037-1044.
22. Lowry, O. H., Rosebrough, N. J., Rarr, A. L. and Randall, R. J., 1951, Protein measurement with the Folin reagent. Journal of Biological Chemistry, 193, 265-275.
23. Middleton, Jr, E. and Kandaswanmi, C., 1993, The flavonoids. In J. B. Harborne (ed.), Advances in Research since 1986 (London: Chapman & Hall), pp. 619-652.
24. Miller, G. L., 1959, Protein determination for a large number of samples. Analytical Chemistry, 31, 964-969.
25. Newton, D. J., Wang, R. and Lu, A. Y., 1995, Cytochrome P450 inhibitors. Evaluation of specificities in the in vitro metabolism of therapeutic agents by human liver microsomes. Drug Metabolism and Disposition, 23, 154-158.
26. Omura, T. and Sato, K. R., 1964, The carbon monoxide-binding pigment of lover microsomes. Evidence for its hemoprotein nature. Journal of Biological Chemistry, 239, 2370-2378.
27. Otton, S. V., Inaba, T. and Kalow, W., 1984, Competitive inhibition of sparteine oxidation in human liver by beta-adrenoceptor antagonists and other cardiovascular drugs. Life Science, 34, 73-80.
28. Rodrigues, A. D., 1999, Integrated cytochrome P450 reaction phenotyping: attempting to bridge the gap between cDNA-expressed cytochromes P450 and native human liver microsomes. Biochemical Pharmacology, 57, 465-480.
29. Sai, Y., Yang, T. J., Krausz, K. W., Gonzalez, F. J. and Gelboin, H. V., 1999, An inhibitory monoclonal antibody to human cytochrome P450 2A6 defines its role in the metabolism of coumarin, 7-ethoxycoumarin and 4-nitroanisole in human liver. Pharmacogentics, 9, 229-237.
30. Sanderink, G. J., Bournique, B., Stevens, J., Petry, M. and Martinet, M., 1997, Involvement of human CYP1A isoenzymes in the metabolism and drug interactions of riluzole in vitro. Journal of Pharmacology and Experimental Therapeutics, 282, 1465-1472.
31. Shimada, T., Yamazaki, H., Mimura, M., Inui, Y. and Guengerich, F. P., 1994, Interindividual variations in human liver cytochrome P-450 enzymes involved in the oxidation of drug, carcinogens and toxic chemicals; studies with liver microsomes of 30 Japanese and 30 Caucasians. Journal of Pharmacology and Experimental Therapeutics, 270, 414-423.
32. Shou, M., Grogan, J., Mancewicz, J. A., Krausz, K. W., Gonzalez, F. J., Gelboin, H. V. and Korzekwa, K. R., 1994a, Activation of CYP3A4: evidence for the simultaneous binding of two substrates in a cytochrome P450 active site. Biochemistry, 33, 6450-6455.
33. Shou, M., Korzekwa, K. R., Krausz, K. W., Crespi, C. L., Gonzalez, F. J. and Gelboin, H. V., 1994b, Regio- and stereo-selective metabolism of phenanthrene by twelve cDNA-expressed human, rodent, and rabbit cytochromes P-450. Cancer Letters, 83, 305-313.
34. Smith, D. A. and Jones, B. C., 1992, Speculations on the substrate structure-activity relationship (SSAR) of cytochrome P450 enzymes. Biochemical Pharmacology, 44, 2089-2098.
35. Spracklin, D. K., Thummel, K. E. and Kharasch, E. D., 1996, Human reductive halothane metabolism in vitro is catalyzed by cytochrome P450 2A6 and 3A4. Drug Metabolism and Disposition, 24, 976-983.
36. Stevens, J. C., White, R. B., Hsu, S. H. and Martinet, M., 1997, Human liver CYP2B6-catalyzed hydroxylation of RP 73401. Journal of Pharmacology and Experimental Therapeutics, 282, 1389-1395.
37. Tyndale, R. F., Kalow, W. and Inaba, T., 1991, Oxidation of reduced haloperidol to haloperidol: involvement of human P450IID6 (sparteine/debrisoquine monooxygenase). British Journal of Clinical Pharmacology, 31, 655-660.
38. Ward, S. and Back, D. J., 1993, Metabolism of gestodene in human liver cytosol and microsomes in vitro. Journal of Steroid Biochemistry and Molecular Biology, 46, 235-243.
39. Yamazaki, H., Inui, Y., Yun, C. H., Guengerich, F. P. and Shimada, T., 1992, Cytochrome P450 2E1 and 2A6 enzymes as major catalysts for metabolic activation of N-nitrosodialkylamines and tobacco-related nitrosamines in human liver microsomes. Carcinogenesis, 13, 1789-1794.
40. Yang, T. J., Krausz, K. W., Shou, M., Yang, S. K., Buters, J. Y., Gonzalez, F. J. and Gelboin, H. V., 1998, Inhibitory monoclonal antibody to human cytochrome P450 2B6. Biochemical Pharmacology, 55, 1633-1640.
41. Yun, C. H., Shimada, T. and Guengerich, F. P., 1992, Roles of human liver cytochrome P4502C and 3A enzymes in the 3-hydroxylation of benzo(a)pyrene. Cancer Research, 52, 1868-1874.
42. Wang, P. P., Beaune, P., Kaminsky, L. S., Dannan, G. A., Kadlubar, F. F., Larrey, D. and Guengerich, F. P., 1983, Purification and characterization of six cytochrome P-450 isozymes from human liver microsomes. Biochemistry, 22, 5375-5383.