Selectivity of polycyclic inhibitors for human cytochrome P450s 1A1, 1A2, and 1B1

Chemical Research in Toxicology

Volumn 11, Issue 9, 1998, Pages 1048-1056

  Shimada, Tsutomu ^a,b   Yamazaki, Hiroshi ^b   Foroozesh, Maryam ^c,d   Hopkins, Nancy E ^c,e   Alworth, William L ^c   Guengerich, F Peter ^a,b  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b OSAKA PREFECTURAL INSTITUTE OF PUBLIC HEALTH   (Japan)

^c XAVIER UNIVERSITY OF LOUISIANA   (United States)

^d TULANE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^e Tulane University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450; ETHOXYRESORUFIN DEETHYLASE; FLAVONE DERIVATIVE; PHENACETIN O DEETHYLASE; PHENANTHRENE DERIVATIVE; PYRENE DERIVATIVE;

ARTICLE; ENZYME ASSAY; ENZYME INHIBITION; ENZYME SPECIFICITY; ENZYME SUBSTRATE COMPLEX; HUMAN;

BIOTRANSFORMATION; CYTOCHROME P-450 CYP1A1; CYTOCHROME P-450 ENZYME SYSTEM; ENZYME INHIBITORS; HUMANS; ISOENZYMES; POLYCYCLIC HYDROCARBONS, AROMATIC; SUBSTRATE SPECIFICITY;

EID: 0031694273     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx980090+     Document Type: Article

References (69)

1. Porter, T. D., and Coon, M. J. (1991) Cytochrome P-450: multiplicity of isoforms, substrates, and catalytic and regulatory mechanisms. J. Biol. Chem. 266, 13469-13472.
2. Ortiz de Montellano, P. R. (1995) Cytochrome P450: Structure, Mechanism, and Biochemistry, 2nd ed., Plenum Press, New York.
3. Nelson, D. R., Koymans, L., Kamataki, T., Stegeman, J. J., Feyereisen, R., Waxman, D. J., Waterman, M. R., Gotoh, O., Coon, M. J., Estabrook, R. W., Gunsalus, I. C., and Nebert, D. W. (1996) P450 superfamily: update on new sequences, gene mapping, accession numbers, and nomenclature. Pharmacogenetics 6, 1-42.
4. Heidelberger, C. (1975) Chemical carcinogenesis. Annu. Rev. Biochem. 44, 79-121.
5. Dipple, A., Michejda, C. J., and Weisburger, E. K. (1985) Metabolism of chemical carcinogens. Pharmacol. Ther. 27, 265-296.
6. Conney, A. H. (1982) Induction of microsomal enzymes by foreign chemicals and carcinogenesis by polycyclic aromatic hydrocarbons: G. H. A. Clowes Memorial Lecture. Cancer Res. 42, 4875-4917.
7. Kellerman, G., Shaw, C. R., and Luyten-Kellerman, M. (1973) Aryl hydrocarbon hydroxylase inducibility and bronchogenic carcinoma. N. Engt. J. Med. 298, 934-937.
8. Kouri, R. E., McKinney, C. E., Slomiany, D. J., Snodgrass, D. R., Wray, N. P., and McLemore, T. L. (1982) Positive correlation between high aryl hydrocarbon hydroxylase activity and primary lung cancer as analyzed in cryopreserved lymphocytes. Cancer Res. 42, 5030-5037.
9. Goto, I., Yoneda, S., Yamamoto, M., and Kawajiri, K. (1996) Prognostic significance of germ Une polymorphisms of the CYP1A1 and glutathione S-transferase genes in patients with non-small cell lung cancer. Cancer Res. 56, 3725-3730.
10. Richardson, H. L., Stier, A. R., and Borsos-Nachtnebel, E. (1952) Liver tumor inhibition and adrenal histologic responses in rats to which 3'-methyl-4-dimethylaminoazobenzene and 20-methylcholanthrene were simultaneously administered. Cancer Res. 12, 356-361.
11. Conney, A. H., Miller, E. C., and Miller, J. A (1956) The metabolism of methylated aminoazo dyes. V. Evidence for induction of enzyme synthesis in the rat by 3-methylcholanthrene. Cancer Res. 16, 450-459.
12. Bhattacharyya, K. K., Brake, P. B., Eltom, S. E., Otto, S. A., and Jefcoate, C. R. (1995) Identification of a rat adrenal cytochrome P450 active in polycyclic hydrocarbon metabolism as rat CYP1B1: demonstration of a unique tissue-specific pattern of hormonal and aryl hydrocarbon receptor-linked regulation. J. Biol. Chem. 270, 11595-11602.
13. EF, representative of a new 1B subfamily of cytochrome P450s. Cloning, sequence determination, and tissue expression. J. Biol. Chem. 269, 14905-14911.
14. Sutter, T. R., Guzman, K., Dold, K. M., and Greenlee, W. F. ( 1991) Targets for dioxin: genes for plasminogen activator inhibitor-2 and interleukin-lβ. Science 254, 415-418.
15. Sutter, T. R., Tang, Y. M., Hayes, C. L., Wo, Y. Y. P., Jabs, E. W., Li, X., Yin, H., Cody, C. W., and Greenlee, W. F. (1994) Complete cDNA sequence of a human dioxin-inducible mRNA identifies a new gene subfamily of cytochrome P450 that maps to chromosome 2. J. Biol Chem. 269, 13092-13099.
16. Liehr, J. G., Ricci, M. J., Jefcoate, C. R., Hannigan, E. V., Hokanson, J. A., and Zhu, B. T. (1995) 4-Hydroxylation of estradiol by human uterine myometrium and myoma mi- crosomes: implications for the mechanism of uterine tumorigen- esis. Proc, Natl, Acad. Sci. U.S.A. 92, 9220-9224.
17. Hayes, C. L., Spink, D. C., Spink, B. C., Cao, J. Q., Walker, N. J., and Sutter, T. R. (1996) 17β-Estradiol hydroxylation catalyzed by human cytochrome P450 1B1. Proc. Natl. Acad. Sci. U.S.A. 93, 9776-9781.
18. Shimada, T., Hayes, C. L., Yamazaki, H., Amin, S., Hecht, S. S., Guengerich, F. P., and Sutter, T. R. (1996) Activation of chemically diverse procarcinogens by human cytochrome P450 1B1. Cancer Res. 56, 2979-2984.
19. Quattrochi, L. C., Okino, S. T., Pendurthi, U. R., and Tukey, R. H. (1985) Cloning and isolation of human cytochrome P-450 cDNAs homologous to dioxin-inducible rabbit mRNAs encoding P-450 4 and P-450 6, DNA 4, 395-400.
20. Jaiswal, A. K., Gonzalez, F. J., and Nebert, D. W. (1985) Human dioxin-inducible cytochrome Pi-450: complementary DNA and amino acid sequence. Science 228, 80-83.
21. Guengerich, F. P. (1995) Human cytochrome P450 enzymes. In Cytochrome P450 (Ortiz de Montellano, P. R., Ed.) 2nd ed., pp 473-535, Plenum Press, New York.
22. Shimada, T., Gillam, E. M. J., Sutter, T. R., Strickland, P. T., Guengerich, F. P., and Yamazaki, H. (1997) Roles of recombinant human cytochrome P450 1B1 in the oxidation of xenobiotic chemicals. Drug Metab. Dispos. 25, 617-622.
23. Ortiz de Montellano, P. R., and Kunze, K. L. (1980) Self-catalyzed inactivation of hepatic cytochrome P-450 by ethynyl substrates. J. Biol. Chem. 255, 5578-5585.
24. Gan, L. S. L., Acebo, A. L., and Alworth, W. L. (1984) 1-Ethynylpyrene, a suicide inhibitor of cytochrome P-450 dependent benzo[a]pyrene hydroxylase activity in liver microsomes. Biochemistry 23, 3827-3836
25. Ortiz de Montellano, P. R., Kunze, K. L., Yost, G. S., and Mico, B. A. (1979) Self-catalyzed destruction of cytochrome P-450: covalent binding of ethynyl sterols to prosthetic heme. Proc. Natl. Acad. Sci U.S.A. 76, 746-749.
26. Komives, E. A., and Ortiz de Montellano, P. R. (1987) Mechanism of oxidation of π bonds by cytochrome P-450: electronic requirements of the transition state in the turnover of phenylacetyienes. J. Biol. Chem. 262, 9793-9802.
27. CaJacob, C. A., Chan, W. K., Shephard, E., and Ortiz de Montellano, P. R., (1988) The catalytic site of rat hepatic lauric acid ω-hydroxylase: protein versus prosthetic heme alkylation in the ω-hydroxylation of acetylenic fatty acids. J. Biol. Chem. 263, 18640-18649.
28. Viaje, A., Lu, J. Y. L., Hopkins, N. E., Nettikumara, A. N., DiGiovanni, J., Alworth, W. L., and Slaga, T. J. (1990) Inhibition of the binding of 7,12-dimethylbenz[a]anthracene and benzo[a]pyrene to DNA in mouse skin epidermis by 1-ethynyl pyre ne. Carcinogenesis 11, 1139-1143.
29. Yun, C.-H-, Hammons, G. J., Jones, G., Martin, M. V., Hopkins, N. E., Alworth, W. L., and Guengerich, F. P. (1992) Modification of cytochrome P450 1A2 enzymes by the mechanism-based inactivator 2-ethynylnaphthalene and the photoaffinity label 4-azidobiphenyl. Biochemistry 31, 10556-10563.
30. Hopkins, N. E., Foroozesh, M. K., and Alworth, W. L. (1992) Suicide inhibitors of cytochrome P450 1A1 and P450 2B1. Biochem. Pharmacol. 44, 787-796.
31. Roberts, E. S., Ballou, D. P., Hopkins, N. E., Alworth, W. L., and Hollenberg, P. F. (1995) Mechanistic studies of 9-ethynylphenanthrene-inactivated cytochrome P450 2B1. Arch. Biochem. Biophys. 323, 303-312.
32. Guengerich, F. P. (1986) Covalent binding to apoprotein is a major fate of heme in a variety of reactions in which cytochrome P-450 is destroyed. Biochem. Biophys. Res. Commun. 138, 193-198.
33. Roberts, E. S., Pernecky, S. J., Alworth, W. L., and Hollenberg, P. F. (1996) A role for threonine 302 in the mechanism-based inactivation of P450 2B4 by 2-ethynylnaphthalene. Arch. Biochem. Biophys. 331, 170-176.
34. Roberts, E. S., Hopkins, N. E., Alworth, W. L., and Hollenberg, P. F. (1993) Mechanism-based inactivation of cytochrome P450 2B1 by 2-ethynylnaphthalene: identification of an active-site peptide. Chem. Res. Toxicol. 6, 470-479.
35. Ortiz de Montellano, P. R., and Reich, N. O. (1986) Inhibition of cytochrome P-450 enzymes. In Cytochrome P-450 (Ortiz de Montellano, P. R., Ed.) pp 273-314, Plenum Press, New York.
36. Hammons, G. J., Alworth, W. L., Hopkins, N. E., Guengerich, F. P., and Kadlubar, F. F. (1989) 2-Ethynylnaphthalene as a mechanism-based inactivator of the cytochrome P-450 catalyzed N-oxidation of 2-naphthylamine. Chem. Res. Toxicol 2, 367-374.
37. Foroozesh, M., Primrose, G., Guo, Z., Bell, L. C., Guengerich, F. P., and Alworth, W.L. (1997) Propynylaryl acetylenes as mechanism-based inhibitors of cytochrome P450 1A1, 1A2, and 2B1 enzymes. Chem. Res. ToxicoL 10, 91-102.
38. Parikh, A., Gillam, E. M. J., and Guengerich, F. P. (1997) Drug metabolism by Escherichia coli expressing human cytochromes P450. Nat Biotechnol. 15, 784-788.
39. Josephy, P. D., Evans, D. H., Parikh, A., and Guengerich, F. P. (1998) Expression of active human cytochrome P450 1A2, NADPHcytochrome P450 reductase, and N-acetyltransferase in Escherichia coli: metabolic activation of aromatic amine mutagens. Chem. Res. Toxicol. 11, 70-74.
40. Shimada, T., Wunsch, R. M., Hanna, I. H., Suiter, T. R., Guengerich, F. P., and Gillam, E. M. J. (1998) Recombinant human cytochrome P450 1B1 expression in Escherichia coli. Arch. Biochem. Biopkys. (in press).
41. pSKl002. Cancer Res. 49, 3218-3228.
42. Gillam, E. M. J., Baba, T., Kim, B.-R., 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.
43. Sandhu, P., Guo, Z., Baba, T., Martin, M. V., Tukey, R. H., and Guengerich, F. P. (1994) 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.
44. Yasukochi, Y., and Masters, B. S. S. (1976) Some properties of a detergent-solubilized NADPH-cytochrome c (cytochrome P-450) reductase purified by biospecific affinity chromatography. J. Biol. Chem. 251, 5337-5344.
45. Guengerich, F. P. (1994) Analysis and characterization of enzymes. In Principles and Methods of Toxicology (Hayes, A. W., Ed.) 3rd ed., pp 1259-1313, Raven Press, New York.
46. Omura, T., and Sato, R. (1964) The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. J. Biol. Chem. 239, 2370-2378.
47. Burke, M. D., and Prough, R. A. (1978) Fluorimetric and Chromatographic methods for measuring microsomal bipheny] hydroxylation. Methods Enzymol. 52, 399-407.
48. Lubet, R. A., Mayer, R. T., Cameron, J. W., Nims, R. W., Burke, M. D., Wolff, T., and Guengerich, F. P. (1985) Dealkylation of pentoxyresorufin: a rapid and sensitive assay for measuring induction of cytochrome(s) P-450 by phenobarbital and other xenobiotics in the rat. Arch. Biochem. Biophys. 238, 43-48.
49. Correia, M. A. (1995) Rat and human liver cytochromes P450. Substrate and inhibitor specificities and functional markers. In Cytochrome P450 (Ortiz de Montellano, P. R., Ed.) 2nd ed., pp 607-630, Plenum Press, New York.
50. Wood, A. W., Levin, W., Lu, A. Y. H., Yagi, H., Hernandez, O., Jerina, D. M., and Conney, A. H. (1976) Metabolism of benzota[a]pyrene and benzo[a]pyrene derivatives to mutagenic products by highly purified hepatic microsomal enzymes. J. Biol. Chem. 251, 4882-4890.
51. Bauer, E., Guo, Z., Ueng, Y.-F-, Bell, L. C., and Guengerich, F. P. (1995) Oxidation of benzo[a]pyrene by recombinant human cytochrome P450 enzymes. Chem. Res. Toxicol. 8, 136-142.
52. Shou, M-, Korzekwa, K. R., Crespi, C. L., Gonzalez, F. J., and Gelboin, H. V. (1994) The role of 12 cDNA-expressed human, rodent, and rabbit cytochromes P450 in the metabolism of benzo[a]pyrene and benzo[a]pyrene trans-7,8-dihydrodiol. Mol. Carcinog. 10, 159-168.
53. Halpert, J. R., and Guengerich, F. P. (1997) Enzyme inhibition and stimulation. In Biotransformation (Guengerich, F. P., Ed.) Vol. 3 of Comprehensive Toxicology (Sipes, I. G., McQueen, C. A., and Gandolfi, A. J., Eds.) pp 21-35, Elsevier Science Ltd., Oxford, U.K.
54. Guengerich, F. P. (1978) Destruction of heme and hemoproteins mediated by liver microsomal reduced nicotinamide adenine dinucleotide phosphate-cytochrome P-450 reductase. Biochemistry 17, 3633-3639.
55. Guengerich, F. P. (1990) Mechanism-based inactivation of human liver cytochrome P-450 IIIA4 by gestodene. Chem. Res. Toxicol. 3, 363-371.
56. Roberts, E. S., Hopkins, N. E., Zaluzec, E. J., Gage, D. A., Alworth, W. L., and Hollenberg, P. F. (1995) Mechanism-based inactivation of cytochrome P450 2B1 by 9-ethynylphenanthrene. Arch. Biochem. Biophys. 323, 295-302.
57. Silverman, R. B. (1995) Mechanism-based enzyme inactivators. Methods Enzymol. 249, 240-283.
58. Otton, S. V., Inaba, T., Mahon, W. A., and Kalow, W. (1982) In vitro metabolism of sparteine by human liver: competitive inhibition by debrisoquine. Can. J. Physiol. Pharmacol. 60, 102-105.
59. Guengerich, F. P., Müller-Enoch, D., and Blair, I. A. (1986) Oxidation of quinidine by human liver cytochrome P-450. Mol. Pharmacol. 30, 287-295.
60. Baldwin, S. J., Bloomer, J. C., Smith, G. J., Ayrton, A. D., Clarke, S. E., and Chenery, R J. (1995) Ketoconazole and sulphaphenazole as the respective selective inhibitors of P4503A and 2C9. Xenobiotica 25, 261-270.
61. Swinney, D. C., So, O. Y., Watson, D. M., Berry, P. W., Webb, A. S., Kertesz, D. J., Shelton, E. J., Burton, P. M., and Walker, K. A. M. (1994) Selective inhibition of mammalian lanosterol 14αdemethylase by RS-21607 in vitro and in vivo. Biochemistry 33, 4702-4713.
62. Kellis, J. T., Jr., and Vickery, L. E. (1984) Inhibition of human estrogen synthetase (aromatase) by flavones. Science 225,1032-1034.
63. Vanden Bossche, H., Moereels, H., and Koymans, L. M. H. (1994) Aromatase inhibitors-mechanisms for non-steroidal inhibitors. Breast Cancer Res. Treat. 30, 43-55.
64. Voorman, R., and Aust, S. D. (1987) Specific binding of polyhalogenated aromatic hydrocarbon inducers of cytochrome P-450d to the cytochrome and inhibition of its estradiol 2-hydroxylase activity. Toxicol. Appl Pharmacol 90, 69-78.
65. Marcus, C. B., Turner, C. R., and Jefcoate, C. R. (1985) Binding of benzo[a]pyrene by purified cytochrome P-450c. Biochemistry 24, 5115-5123.
66. Turner, C. R., Marcus, C. B., and Jefcoate, C. R. (1985) Selectivity in the binding of hydroxylated benzo[a]pyrene derivatives to purified cytochrome P-450c. Biochemistry 24, 5124-5130.
67. Imai, Y., Hashimoto-Yutsudo, C., Satake, H., Girardin, A., and Sato, R. (1980) Multiple forms of cytochrome P-450 purified from liver microsomes of phénobarbital- and 3-methylcholanthrenepretreated rabbits. I. Resolution, purification, and molecular properties. J. Biochem, 88, 489-503.
68. Miller, D. M., Aust, A. E., Voorman, R., and Aust, S. D. (1988) Inhibition of 2-aminofluorene mutagenesis in bacteria by inducers of cytochrome P-450d. Carcinogenesis 9, 327-329.
69. Savas, Ü., Carstens, C. P., and Jefcoate, C. R. (1997) Recombinant mouse CYP1B1 expressed in Escherichia coli exhibits selective binding by polycyclic hydrocarbons and metabolism which parallels C3H10T1/2 cell microsomes, but differs from human recombinant CYP1B1. Arch. Biochem. Biophys. 347, 181-192.