Specificity of substrate and inhibitor probes for cytochrome P450s: Evaluation of in vitro metabolsm using cDNA-exoressed human P450s and human liver microsomes

Xenobiotica

Volumn 26, Issue 7, 1996, Pages 681-693

  Ono, S ^a,b   Hatanaka, T ^a   Hotta, H ^a   Satoh, T ^b   Gonzalez, F J ^c   Tsutsui, M ^a  

^a Amersham KK   (Japan)

^b CHIBA UNIVERSITY   (Japan)

^c NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 METHYLPYRAZOLE; ALPHA NAPHTHOFLAVONE; ANILINE; COUMARIN; CYTOCHROME P450 ISOENZYME; DIAZEPAM; DIETHYLDITHIOCARBAMIC ACID; ELLIPTICINE; ENZYME INHIBITOR; FURAFYLLINE; KETOCONAZOLE; METHOXSALEN; PIPERONYL BUTOXIDE; PROADIFEN; QUERCETIN; QUINIDINE; SULFAPHENAZOLE; TOLBUTAMIDE; TRANYLCYPROMINE; TROLEANDOMYCIN;

ARTICLE; CONTROLLED STUDY; ENZYME INHIBITION; ENZYME SPECIFICITY; ENZYME SUBSTRATE; HEPATOMA CELL; HUMAN; HUMAN CELL; HUMAN TISSUE; IN VITRO STUDY; LIVER MICROSOME;

EID: 0030056594     PISSN: 00498254     EISSN: None     Source Type: Journal    
DOI: 10.3109/00498259609046742     Document Type: Article

References (42)

1. ABDEL-HAMID, M. E., and ABUIRJEIE, M. A., 1988, Determination of diazepam and oxazepam using high-performance liquid chromatography and fourth-derivative spectrophotometric techniques. Analyst, 113, 1443-1446.
2. AOYAMA, T., GELBOIN, H. V., and GONZALEZ, F. J., 1990b, Mutagenic activation of 2-amino-3-methylimidazo[4,5-f]quinoline by complementary DNA-expressed human liver P-450. Cancer Research, 50, 2060-2063.
3. 1. Proceedings of the National Academy of Sciences, USA, 87, 4790-4793.
4. BIRKETT, D. J., MACKENZIE, P. I., VERONESE, M. E., and MINERS, J. O., 1993, In vitro approaches can predict human drug metabolism. Trends in Pharmacological Sciences, 14, 292-294.
5. CHEN, L.-S., YASUMORI, T., YAMAZOE, Y., and KATO, R., 1993, Hepatic microsomal tolbutamide hydroxylation in Japanese : in vitro evidence for rapid and slow metabolizers. Pharmacogenetics, 3, 77-85.
6. CLEJAN, L. A., and CEDERBAUM, A. I., 1991, Role of iron, hydrogen peroxide and reactive species in microsomal oxidation of glycerol to formaldehyde. Archives in Biochemistry and Biophysics, 285, 83-89.
7. CLEJAN, L. A., and CEDERBAUM, A. I., 1992, Structural determinations for alcohol substrates to be oxidized to formaldehyde by rat liver microsomes. Archives in Biochemistry and Biophysics, 298, 105-113.
8. CRESPI, C. L., PENMAN, B. W., LEAKEY, J. A. E., ARLOTTO, M. P., STARK, A., PARKINSON, A., TURNER, T., STEIMEL, D., RUDO, K., DAVIES, R. L., and LANGENBACH, R., 1990, 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.
9. DOECKE, C. J., SAMSON, L. N., and MCMANUS, M. E., 1990, Phenytoin 4-hydroxylation by rabbit liver P450IIC3 and identification of orthologs in human liver microsomes. Biochemical and Biophysical Research Communications, 166, 860-866.
10. FORRESTER, L. M., HENDERSON, C. J., GLANCEY, M. J., BACK, D. J., PARK, B. K., BALL, S. E., KITTERINGHAM, N. R., MCLAREN, A. W., MILES, J. S., SKETT, P., and WOLF, C. R., 1992, Relative expression of cytochrome P450 isozymes in human liver and association with the metabolism of drugs and xenobiotics. Biochemical Journal, 281, 359-368.
11. GONZALEZ, F. J., AOYAMA, T., and GELBOIN, H. V., 1991, Expression of mammalian cytochrome P450 using vaccinia virus. In Methods in Enzymology, edited by M. R. Waterman and E. F. Johnson (San Diego: Academic), 206, pp. 85-92.
12. GRANT, D. M., CAMPBELL, M. E., TANG, B. K., and KALOW, W., 1987, Biotransformation of caffeine by microsomes from human liver. Biochemical Pharmacology, 36, 1251-1260.
13. 2 hepatoma cell line. Biochemical Pharmacology, 21, 4111-4116.
14. GUENGERICH, F. P., 1944, Catalytic selectivity of human cytochrome P450 enzymes: relevance to drug metabolism and toxicity. Toxicology Letters, 70, 133-138.
15. HAKKOLA, J., PASANEN, M., PURKUNEN, R., SAARIKOSKI, S., PELKONEN, O., MÄENPÄÄ, J., RANE, A., and RAUNIO, H., 1994, Expression of xenobiotic-metabolizing cytochrome P450 forms in human adult and fetal liver. Biochemical Pharmacology, 48, 59-64.
16. 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.
17. IMAI, Y., ITO, A., and SATO, R., 1966, Evidence for biochemically different types of vesicles in the hepatic microsomal fraction. Journal of Biochemistry, 60, 417-428.
18. IMAOKA, S., TERANO, Y., and FUNAE, Y., 1989, Expression of four phenobarbital-inducible cytochrome P-450s in liver, kidney, and lung of rats. Journal of Biochemistry, 105, 939-945.
19. KAMATAKI, T., MAEDA, K., YAMAZOE, Y., NAGAI, T., and KATO, R., 1983, Sex-difference of cytochrome P-450 in the rat: purification, characterization, and quantification of constitutive forms of cytochrome P-450 from liver microsomes of male and female rats. Archives of Biochemistry and Biophysics, 225, 758-770.
20. KATO, R., and YAMAZOE, Y., 1994, The importance of substrate concentration in determining cytochromes P450 therapeutically relevant in vivo. Pharmacogenetics, 4, 359-362.
21. KIMURA, S., PASTEWKA, J., GELBOIN, H. V., and GONZALEZ, F. J., 1987, cDNA and amino acid sequences of two members of the human IIC gene subfamily. Nucleic Acids Research, 15, 10053-10054.
22. KRONBACH, T., MATHYS, D., GUT, J., CATIN, T., and MEYER, U. A., 1987, High-performance liquid chromatographic assays for bufuralol 1′-hydroxylase, debrisoquine 4-hydroxylase, and dextromethorphan O-demethylase in microsomes and purified cytochrome P-450 isozymes of human liver. Analytical Biochemistry, 162, 24-32.
23. LOWRY, O. H., ROSEBROUGH, N. J., FARR, A. L., and RANDALL, R. L., 1951, Protein measurement with the Folin phenol reagent. Journal of Biological Chemistry, 193, 265-275.
24. MATSUBARA, T., KOIKE, M., TOUCHI, A., TOCHINO, Y., and SUGENO, K., 1976, Quantitative determination of cytochrome P-450 in rat liver homogenate. Analytical Biochemistry, 75, 596-603.
25. NAGATA, K., MATSUNAGA, T., GILLETTE, J., GELBOIN, H. V., and GONZALEZ, F. J., 1987, Rat testosterone 7α-hydroxylase. Isolation, sequence and expression of cDNA and its developmental regulation and induction by 3-methoxycholanthrene. Journal of Biological Chemistry, 262, 2787-2793.
26. NARIMATSU, S., MASUBUCHI, Y., HOSOKAWA, S., OHMORI, S., KITADA, M., and SUZUKI, T., 1994, Involvement of a cytochrome P4502D subfamily in human liver microsomal bunitrolol 4-hydroxylation. Biological Pharmacology Bulletin, 17, 803-807.
27. NEWTON, D. J., WANG, R. W., and LU, A. Y. H., 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.
28. OMURA, T., and SATO, R., 1964, Carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. Journal of Biological Chemistry, 239, 2370-2378.
29. ONO, S., TSUTSUI, M., GONZALES, F. J., SATOH, T., MASUBUCHI, Y., HORIE, T., SUZUKI, T., and NARIMATSU, S., 1995a, Oxidative metabolism of bunitrolol by complementary DNA-expressed human cytochrome P450 isozymes in a human hepatoma cell line (Hep G2) using recombinant vaccinia virus. Pharmacogenetics, 5, 97-102.
30. ONO, S., HATANAKA, T., HOTTA, H., TSUTSUI, M., SATOH, T., and GONZALEZ, F. J., 1995b, Chlorzoxazone is metabolized by human CYP1A2 as well as by human CYP2E1. Pharmacogenetics, 5, 143-150.
31. RELLING, M. V., AOYAMA, T., GONZALEZ, F. J., and MEYER, U. A., 1990, Tolbutamide and mephenytoin hydroxylation by human cytochrome P450s in the CYP2C subfamily. Journal of Pharmacology and Experimental Therapeutics, 252, 442-447.
32. RETTIE, A. E., KORZEKWA, K. R., KUNZE, K. L., LAWRENCE, R. F., EDDY, A. C., AOYAMA, T., GELBOIN, H. V., GONZALEZ, F. J., and TRAGER, W. F., 1992, Hydroxylation of warfarin by human cDNA-expressed cytochrome P-450: a role for P-4502C9 in the etiology of (S)-warfarin-drug interactions. Chemical Research and Toxicology, 5, 54-59.
33. RETTIE, A. E., WIENKERS, L. C., GONZALEZ, F. J., TRAGER, W. F., and KORZEKWA, K. R., 1994, Impaired (S)-warfarin metabolism catalysed by the R144C allelic variant of CYP2C9. Pharmacogenetics, 4, 39-42.
34. RODRIGUES, A. D., 1994, Use of in vitro human metabolism studies in drug development. Biochemical Pharmacology, 48, 2147-2156.
35. 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 drugs, carcinogens and toxic chemicals: studies with liver microsomes of 30 Japanese and 30 Caucasians. Journal of Pharmacological and Experimental Therapeutics, 270, 414-423.
36. TASSANEEYAKUL, W., BIRKITT, D. J., VERONESE, M. E., MCMANUS, M. E., TUKEY, R. H., QUATTROCHI, L. C., GELBOIN, H. V., and MINERS, J. O., 1993, Specificity of substrate and inhibitor probes for human cytochromes P450 1A1 and 1A2. Journal of Pharmacology and Experimental Therapeutics, 265, 401-407.
37. TSYRLOV, I. B., MIKHAILENKO, V. M., and GELBOIN, H. V., 1994, Isozyme- and species-specific susceptibility of cDNA-expressed CYP1A P-450s to different flavonoids. Biochimica et Biophysica Acta, 1205, 325-335.
38. TYNDALE, R., AOYAMA, T., BROLY, F., MATSUNAGA, T., INABA, T., KALOW, W., GELBOIN, H. V., MEYER, U. A., and Gonzalez, F. J., 1991, Identification of a new variant CYP2D6 allele lacking the codon encoding Lys-281 : possible association with the poor metabolizer phenotype. Pharmacogenetics, 1, 26-32.
39. WRIGHTON, S. A., VANDENBRANDEN, M., STEVENS, J. C., SHIPLEY, L. A., and RING, B. J., 1993, In vitro methods for assessing human hepatic drug metabolism: their use in drug development. Drug Metabolism Reviews, 25, 453-484.
40. YAMANO, S., AOYAMA, T., MCBRIDE, O. W., HARDWICK, J. P., GELBOIN, H. V., and GONZALEZ, F. J., 1989, Human NADPH-P450 oxido-reductase: complementary DNA cloning, sequence and vaccinia virus-mediated expression and localization of the CYPOR gene to chromosome 7. Molecular Pharmacology, 35, 83-88.
41. YAMANO, S., TATSUNO, J., and GONZALEZ, F. J., 1990, The CYP2A3 gene product catalyzes coumarin 7-hydroxylation in human liver microsomes. Biochemistry, 29, 1322-1329.
42. YASUMORI, T., MURAYAMA, N., YAMAZOE, Y., and KATO, R., 1990, Polymorphism in hydroxylation of mephenytoin and hexobarbital stereoisomers in relation to hepatic P-450 human-2. Clinical Pharmacology and Therapeutics, 47, 313-322.