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Activation of Chemically Diverse Procarcinogens by Human Cytochrome P-450 1B1¹

Department of Biochemistry and Center in Molecular Toxicology, Vanderbilt University School of Medicine, Nashville, Tennessee 37232 [T. S., F. P. G.]; Department of Environmental Health Sciences, The Johns Hopkins School of Hygiene and Public Health, Baltimore, Maryland 21205 [C. L. H., T. R. S.]; Osaka Prefectural Institute of Public Health, Nakamichi 1-chome, Higashinari-ku, Osaka 537, Japan [H. Y.]; and American Health Foundation, Valhalla, New York 10595 [S. A., S. S. H.]

A human cytochrome P-450 (P450) 1B1 cDNA was expressed in Saccharomyces cerevisiae, and the microsomes containing P450 1B1 were used to examine the selectivity of this enzyme in the activation of a variety of environmental carcinogens and mutagens in Salmonella typhimurium TA1535/pSK1002 or NM2009 tester strains, using the SOS response as an end point of DNA damage. We also determined and compared these activities of P450 1B1 with those catalyzed by recombinant human P450s 1A1 and 1A2, which were purified from membranes of Escherichia coli. The carcinogenic chemicals tested included 27 polycyclic aromatic hydrocarbons and their dihydrodiol derivatives, 17 heterocyclic and aryl amines and aminoazo dyes, three mycotoxins, two nitroaromatic hydrocarbons, N-nitrosodimethylamine, vinyl carbamate, and acrylonitrile. Among the three P450 enzymes examined here, P450 1B1 was found to have the highest catalytic activities for the activation of 11,12-dihydroxy-11,12-dihydrodibenzo[a,l]pyrene, 1,2-dihydroxy-1,2-dihydro-5-methylchrysene, (+)-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene, 11,12-dihydroxy-11,12-dihydrobenzo[g]chrysene, 3,4-dihydroxy-3,4-dihydrobenzo[c]phenanthrene, 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole, 2-aminoanthracene, 3-methoxy-4-aminoazobenzene, and 2-nitropyrene. P450 1B1 also catalyzed the activation of 2-amino-3,5-dimethylimidazo[4,5-f]quinoline, 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline, 2-amino-3-methylimidazo[4,5-f]quinoline, 2-aminofluorene, 6-aminochrysene and its 1,2-dihydrodiol, (-)-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene, 1,2-dihydroxy-1,2-dihydrochrysene, 1,2-dihydroxy-1,2-dihydro-5,6-dimethylchrysene, 2,3-dihydroxy-2,3-dihydrofluoranthene, 3,4-dihydroxy-3,4-dihydro-7,12-dimethylbenz[a]anthracene, and 6-nitrochrysene to appreciable extents. However, P450 1B1 did not produce genotoxic products from benzo[a]pyrene, trans-3,4-dihydroxy-3,4-dihydrobenzo[a]anthracene, trans-8,9-dihydroxy-8,9-dihydrobenzo[a]anthracene, 7,12-dimethylbenz[a]anthracene and its cis-5,6-dihydrodiol, 5-methylchrysene, 11,12-dihydroxy-11,12-dihydro-3-methylcholanthrene, 1,2-dihydroxy-1,2-dihydro-6-methylchrysene, benzo[c]phenanthrene, 2-amino-6-methyldipyrido[1,2-a:3',2'-d]imidazole, 2-acetylaminofluorene, benzidine, 2-naphthylamine, aflatoxin B₁, aflatoxin G₁, sterigmatocystin, N-nitrosodimethylamine, vinyl carbamate, or acrylonitrile in this assay system. P450 1B1 is expressed constitutively in extrahepatic organs, including fetal tissue samples, and is highly inducible in various organs by 2,3,7,8-tetrachlorodibenzo-p-dioxin and related compounds in experimental animal models. Thus, activation of procarcinogens by P450 1B1 may contribute to human tumors of extrahepatic origin.

¹ This work was supported in part by USPHS Grants CA44353, ES00267 (F. P. G.), ES03819, ES06071 (T. R. S.), and CA44377 (S. S. H.) and by grants from the Ministry of Education, Science, Sports and Culture of Japan (T. S.). C. L. H. is supported by Training Grant ES07141.

² Present address: Osaka Prefectural Institute of Public Health, Nakamichi 1-chome, Higashinari-ku, Osaka 537, Japan.

³ Requests for reprints should be addressed to either of these authors, at Department of Biochemistry and Center in Molecular Toxicology, Vanderbilt University School of Medicine, Nashville, TN 37232 (F. P. G.), or Department of Environmental Health Sciences, The Johns Hopkins School of Hygiene and Public Health, Baltimore, MD 21205.

Received 1/30/96. Accepted 4/30/96.

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				P. Lin, S.-W. Hu, and T.-H. Chang Correlation between Gene Expression of Aryl Hydrocarbon Receptor (AhR), Hydrocarbon Receptor Nuclear Translocator (Arnt), Cytochromes P4501A1 (CYP1A1) and 1B1 (CYP1B1), and Inducibility of CYP1A1 and CYP1B1 in Human Lymphocytes Toxicol. Sci., January 1, 2003; 71(1): 20 - 26. [Abstract] [Full Text] [PDF]

				S. R. Kondraganti, W. Jiang, and B. Moorthy Differential Regulation of Expression of Hepatic and Pulmonary Cytochrome P4501A Enzymes by 3-Methylcholanthrene in Mice Lacking the CYP1A2 Gene J. Pharmacol. Exp. Ther., December 1, 2002; 303(3): 945 - 951. [Abstract] [Full Text] [PDF]

				J. C. Rowlands, R. Hakkak, M. J. J. Ronis, and T. M. Badger Altered Mammary Gland Differentiation and Progesterone Receptor Expression in Rats Fed Soy and Whey Proteins Toxicol. Sci., November 1, 2002; 70(1): 40 - 45. [Abstract] [Full Text] [PDF]

				C. Sachse, G. Smith, M. J.V. Wilkie, J. H. Barrett, R. Waxman, F. Sullivan, D. Forman, D. T. Bishop, and C.R. Wolf A pharmacogenetic study to investigate the role of dietary carcinogens in the etiology of colorectal cancer Carcinogenesis, November 1, 2002; 23(11): 1839 - 1850. [Abstract] [Full Text] [PDF]

				H. K. Crewe, L. M. Notley, R. M. Wunsch, M. S. Lennard, and E. M. J. Gillam Metabolism of Tamoxifen by Recombinant Human Cytochrome P450 Enzymes: Formation of the 4-Hydroxy, 4'-Hydroxy and N-Desmethyl Metabolites and Isomerization of trans-4-Hydroxytamoxifen Drug Metab. Dispos., August 1, 2002; 30(8): 869 - 874. [Abstract] [Full Text] [PDF]

				T. Shimada, K. Inoue, Y. Suzuki, T. Kawai, E. Azuma, T. Nakajima, M. Shindo, K. Kurose, A. Sugie, Y. Yamagishi, et al. Arylhydrocarbon receptor-dependent induction of liver and lung cytochromes P450 1A1, 1A2, and 1B1 by polycyclic aromatic hydrocarbons and polychlorinated biphenyls in genetically engineered C57BL/6J mice Carcinogenesis, July 1, 2002; 23(7): 1199 - 1207. [Abstract] [Full Text] [PDF]

				L. Muskhelishvili, L. D. Freeman, J. R. Latendresse, and T. J. Bucci An Immunohistochemical Label to Facilitate Counting of Ovarian Follicles Toxicol Pathol, April 1, 2002; 30(3): 400 - 402. [Abstract] [PDF]

				D. C. Spink, B. H. Katz, M. M. Hussain, B. C. Spink, S. J. Wu, N. Liu, R. Pause, and L. S. Kaminsky Induction of CYP1A1 and CYP1B1 in T-47D Human Breast Cancer Cells by Benzo[a]pyrene Is Diminished by Arsenite Drug Metab. Dispos., March 1, 2002; 30(3): 262 - 269. [Abstract] [Full Text] [PDF]

				E. Aklillu, M. Oscarson, M. Hidestrand, B. Leidvik, C. Otter, and M. Ingelman-Sundberg Functional Analysis of Six Different Polymorphic CYP1B1 Enzyme Variants Found in an Ethiopian Population Mol. Pharmacol., March 1, 2002; 61(3): 586 - 594. [Abstract] [Full Text] [PDF]

				B. Moorthy, K. P. Miller, W. Jiang, and K. S. Ramos The atherogen 3-methylcholanthrene induces multiple DNA adducts in mouse aortic smooth muscle cells: role of cytochrome P4501B1 Cardiovasc Res, March 1, 2002; 53(4): 1002 - 1009. [Abstract] [Full Text] [PDF]

				R. N. Hines and D. G. McCarver The Ontogeny of Human Drug-Metabolizing Enzymes: Phase I Oxidative Enzymes J. Pharmacol. Exp. Ther., February 1, 2002; 300(2): 355 - 360. [Abstract] [Full Text] [PDF]

				S. A. Larsen-Su and D. E. Williams Transplacental Exposure to Indole-3-carbinol Induces Sex-Specific Expression of CYP1A1 and CYP1B1 in the Liver of Fischer 344 Neonatal Rats Toxicol. Sci., December 1, 2001; 64(2): 162 - 168. [Abstract] [Full Text] [PDF]

				N. Hatanaka, H. Yamazaki, R. Kizu, K. Hayakawa, Y. Aoki, M. Iwanari, M. Nakajima, and T. Yokoi Induction of cytochrome P450 1B1 in lung, liver and kidney of rats exposed to diesel exhaust Carcinogenesis, December 1, 2001; 22(12): 2033 - 2038. [Abstract] [Full Text] [PDF]

				J. C. Rowlands, L. He, R. Hakkak, M. J. J. Ronis, and T. M. Badger Soy and Whey Proteins Downregulate DMBA-Induced Liver and Mammary Gland CYP1 Expression in Female Rats J. Nutr., December 1, 2001; 131(12): 3281 - 3287. [Abstract] [Full Text] [PDF]

				Y.-J. Chun, S. Kim, D. Kim, S.-K. Lee, and F. P. Guengerich A New Selective and Potent Inhibitor of Human Cytochrome P450 1B1 and Its Application to Antimutagenesis Cancer Res., November 1, 2001; 61(22): 8164 - 8170. [Abstract] [Full Text] [PDF]

				T. Shimada, Y. Oda, E. M. J. Gillam, F. P. Guengerich, and K. Inoue Metabolic Activation of Polycyclic Aromatic Hydrocarbons and Other Procarcinogens by Cytochromes P450 1A1 and P450 1B1 Allelic Variants and Other Human Cytochromes P450 in Salmonella typhimurium NM2009 Drug Metab. Dispos., September 1, 2001; 29(9): 1176 - 1182. [Abstract] [Full Text] [PDF]

				S. Dawling, N. Roodi, R. L. Mernaugh, X. Wang, and F. F. Parl Catechol-O-Methyltransferase (COMT)-mediated Metabolism of Catechol Estrogens: Comparison of Wild-Type and Variant COMT Isoforms Cancer Res., September 1, 2001; 61(18): 6716 - 6722. [Abstract] [Full Text] [PDF]

				D. P. Bofinger, L. Feng, L.-H. Chi, J. Love, F. D. Stephen, T. R. Sutter, K. G. Osteen, T. G. Costich, R. E. Batt, S. T. Koury, et al. Effect of TCDD Exposure on CYP1A1 and CYP1B1 Expression in Explant Cultures of Human Endometrium Toxicol. Sci., August 1, 2001; 62(2): 299 - 314. [Abstract] [Full Text] [PDF]

				D. D. Vakharia, N. Liu, R. Pause, M. Fasco, E. Bessette, Q.-Y. Zhang, and L. S. Kaminsky Polycyclic Aromatic Hydrocarbon/Metal Mixtures: Effect on PAH Induction of CYP1A1 in Human HepG2 Cells Drug Metab. Dispos., July 1, 2001; 29(7): 999 - 1006. [Abstract] [Full Text] [PDF]

				J. Hukkanen, O. Pelkonen, and H. Raunio Expression of xenobiotic-metabolizing enzymes in human pulmonary tissue: possible role in susceptibility for ILD Eur. Respir. J., July 1, 2001; 18(32_suppl): 122S - 126s. [Abstract] [Full Text] [PDF]

				S. D. Spivack, G. J. Hurteau, A. A. Reilly, K. M. Aldous, X. Ding, and L. S. Kaminsky CYP1B1 Expression in Human Lung Drug Metab. Dispos., June 1, 2001; 29(6): 916 - 922. [Abstract] [Full Text]

				M.-F. Yueh, N. Nguyen, M. Famourzadeh, C. P. Strassburg, Y. Oda, F.P. Guengerich, and R. H. Tukey The contribution of UDP-glucuronosyltransferase 1A9 on CYP1A2-mediated genotoxicity by aromatic and heterocyclic amines Carcinogenesis, June 1, 2001; 22(6): 943 - 950. [Abstract] [Full Text] [PDF]

				Y. Ko, J. Abel, V. Harth, P. Brode, C. Antony, S. Donat, H.-P. Fischer, M. E. Ortiz-Pallardo, R. Thier, A. Sachinidis, et al. Association of CYP1B1 Codon 432 Mutant Allele in Head and Neck Squamous Cell Cancer Is Reflected by Somatic Mutations of p53 in Tumor Tissue Cancer Res., June 1, 2001; 61(11): 4398 - 4404. [Abstract] [Full Text] [PDF]

				C. J. MacDonald, H. P. Ciolino, and G. C. Yeh Dibenzoylmethane Modulates Aryl Hydrocarbon Receptor Function and Expression of Cytochromes P450 1A1, 1A2, and 1B1 Cancer Res., May 1, 2001; 61(10): 3919 - 3924. [Abstract] [Full Text]

				B. Rochat, J. M. Morsman, G. I. Murray, W. D. Figg, and H. L. McLeod Human CYP1B1 and Anticancer Agent Metabolism: Mechanism for Tumor-Specific Drug Inactivation? J. Pharmacol. Exp. Ther., April 13, 2001; 296(2): 537 - 541. [Abstract] [Full Text]

				Y. J. Chun, S. Y. Ryu, T. C. Jeong, and M. Y. Kim Mechanism-Based Inhibition of Human Cytochrome P450 1A1 by Rhapontigenin Drug Metab. Dispos., April 1, 2001; 29(4): 389 - 393. [Abstract] [Full Text]

				L. Muskhelishvili, P. A. Thompson, D. F. Kusewitt, C. Wang, and F. F. Kadlubar In Situ Hybridization and Immunohistochemical Analysis of Cytochrome P450 1B1 Expression in Human Normal Tissues J. Histochem. Cytochem., February 1, 2001; 49(2): 229 - 236. [Abstract] [Full Text]

				S. L. Barnes, K. W. Singletary, and R. Frey Ethanol and acetaldehyde enhance benzo[a]pyrene-DNA adduct formation in human mammary epithelial cells Carcinogenesis, November 1, 2000; 21(11): 2123 - 2128. [Full Text] [PDF]

				A. C. Deitz, W. Zheng, M. A. Leff, M. Gross, W.-Q. Wen, M. A. Doll, G. H. Xiao, A. R. Folsom, and D. W. Hein N-Acetyltransferase-2 Genetic Polymorphism, Well-done Meat Intake, and Breast Cancer Risk among Postmenopausal Women Cancer Epidemiol. Biomarkers Prev., September 1, 2000; 9(9): 905 - 910. [Abstract] [Full Text]

				C. Albert, O. Barbier, M. Vallee, G. Beaudry, A. Belanger, and D. W. Hum Distribution of Uridine Diphosphate-Glucuronosyltransferase (UGT) Expression and Activity in Cynomolgus Monkey Tissues: Evidence for Differential Expression of Steroid-Conjugating UGT Enzymes in Steroid Target Tissues Endocrinology, July 1, 2000; 141(7): 2472 - 2480. [Abstract] [Full Text] [PDF]

				I. H. Hanna, S. Dawling, N. Roodi, F. P. Guengerich, and F. F. Parl Cytochrome P450 1B1 (CYP1B1) Pharmacogenetics: Association of Polymorphisms with Functional Differences in Estrogen Hydroxylation Activity Cancer Res., July 1, 2000; 60(13): 3440 - 3444. [Abstract] [Full Text]

				S. M. Heidel, P. S. MacWilliams, W. M. Baird, W. M. Dashwood, J. T. M. Buters, F. J. Gonzalez, M. C. Larsen, C. J. Czuprynski, and C. R. Jefcoate Cytochrome P4501B1 Mediates Induction of Bone Marrow Cytotoxicity and Preleukemia Cells in Mice Treated with 7,12-Dimethylbenz[a]anthracene Cancer Res., July 1, 2000; 60(13): 3454 - 3460. [Abstract] [Full Text]

				C. R. Jefcoate, J. G. Liehr, R. J. Santen, T. R. Sutter, J. D. Yager, W. Yue, S. J. Santner, R. Tekmal, L. Demers, R. Pauley, et al. Chapter 5: Tissue-Specific Synthesis and Oxidative Metabolism of Estrogens J Natl Cancer Inst Monographs, July 1, 2000; 2000(27): 95 - 112. [Abstract] [Full Text] [PDF]