Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones

References

• AOYAMA, T., KORZEKWA, K., NAGATA, K., GILLETTE, J., GELBOIN, H. V. and GONZALEZ, F. J., 1990, Estradiol metabolism by complementary deoxyribonucleic acid-expressed human cytochrome P450s. Endocrinology, 126, 3101–3106.
   PubMed Web of Science ®Google Scholar
• BOCKER, R. H. AND GUENGERICH, F. P., 1986, Oxidation of 4-aryl and 4-alkyl-substituted 2,6-dimethy1-3,5-bis(alkoxycarbony1)-1,4-dihydropyridines by human liver microsomes and immunochemical evidence for the involvement of a form of cytochrome P-450. Journal of Medicinal Chemistry, 29, 1596–1603.
   Google Scholar
• BRIAN, W. R., SARI, M.-A., IWASAKI, M., SHIMADA, T., KAMINSKY, L. S. AND GUENGERICH, F. P., 1990, Catalytic activities of human liver cytochrome P-450 IIIA4 expressed in Saccharomyces cerevisiae. Biochemistry, 29, 11280–11292.
   Google Scholar
• DISTLERATH, L. M., REILLY, P. E. B., MARTIN, M. V., DAVIS, G. G., WILKINSON, G. R. AND GUENGERICH, F. P., 1985, Purification and characterization of the human liver cytochrome P-450 forms involved in debrisoquine 4-hydroxylation and phenacetin 0-deethylation, two prototypes for genetic polymorphism in oxidative drug metabolism. Journal of Biological Chemistry, 260, 9057–9067.
   Google Scholar
• FUNAE, Y. AND IMAOKA, S., 1993, Cytochrome P450 in rodents. In Cytochrome P450, edited by J. B. Schenkman and H. Greim (Berlin: Springer), pp. 221–238.
   Google Scholar
• GUENGERICH, F. P., 1992, Characterization of human cytochrome P450 enzymes. F ASEB Journal, 6, 745–748.
   PubMed Web of Science ®Google Scholar
• GUENGERICH, F. P., 1996, In vitro techniques for studying drug metabolism. Journal of Pharmacokinaeics and Biopharmaceutics, 24, 521–533.
   PubMedGoogle Scholar
• GUENGERICH, F. P., G1LLAM, M. J. AND SHIMADA, T., 1996, New applications of bacterial systems to problems in toxicology. Critical Review in Toxicology. 26, 551–583.
   Google Scholar
• GUENGERICH, F. P., MARTIN, M. V., BEAUNE, P. H., KREMERS, P., WOLFF, T. AND WAXMAN, D. J., 1986, Characterization of rat and human liver microsomal cytochrome P-450 forms involved in nifedipine oxidation, a prototype for genetic polymorphism in oxidative drug metabolism. journal of Biological Chemistry, 261, 5051–5060.
   PubMed Web of Science ®Google Scholar
• HONMA, K., MATSUMOTO, M., TAICESHITA, E., IR', H., YASUKURA, T., SATO, S. AND MATSUO N., 1994, Assessment of the urinary steroid profiles in new born infants by GC/MS selected ion monitoring system. Hormone to Rinshou, 42, 623–629.
   Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• IMAOKA, S., YAMADA, T., HIROI, T., HAYASHI, K., SAKAKI, T., YABUSAKI, Y. AND FUNAE, Y., 1996, Multiple forms of human P450 expressed in Saccharomyces cerevisiae. Biochemical Pharmacology, 51, 1041–1050.
   PubMed Web of Science ®Google Scholar
• JONSSON, G., ASTROM, A. AND ANDERSSON, P., 1995, Budesonide is metabolized by cytochrome P450 3A (CYP 3A) enzymes in human liver. Drug Metabolism and Disposition, 23, 137–142.
   PubMed Web of Science ®Google Scholar
• KAGAWA, N. AND WATERMAN, M. R., 1995, Regulation of steroidogenic and related P450s. In Cytochrome P450: Structure, Mechanism and Biochemistry, 2nd edn, edited by P. R. Ortiz de Montellano (New York: Plenum), pp. 419–442.
   Google Scholar
• KERLAN, V., DREANO, Y., BERCOVICI, J. P., BEAUNE, P. H., FLocH, H. H. AND BERTHOU, F., 1992, Nature of cytochromes P450 involved in the 2- /4-hydroxylations of estradiol in human liver microsomes. Biochemical Pharmacology, 44, 1745–1756.
   PubMed Web of Science ®Google Scholar
• KITADA, M., KAMATAKI, T., ITAHASHI, K., RIKIHISA, T. AND KANAKUBO, Y., 1987, P-450 HFLa, a form of cytochrome P-450 purified from human fetal livers, is the 16a-hydroxylase of dehydro-epiandrosterone 3-sulfate. Journal of Biological Chemistry, 262, 13534–13537.
   PubMed Web of Science ®Google Scholar
• NEBERT, D. W., 1993, Elevated estrogen 16a-hydroxylase activity: is this a genotoxic or nongenotoxic biomarker in human breast cancer risk ?Journal of the National Cancer Institute, 85, 1888–1891.
   PubMed Web of Science ®Google Scholar
• NIWA, T., KANEKO, H., NARITOMI, Y., TOGAWA, A., SHIRAGA, T., IWASAKI, K., TOZUKA, Z. AND HATA, T., 1995, Species and sex differences of testosterone and nifedipine oxidation in liver microsomes of rat, dog and monkey. Xenobiotica, 25, 1041–1049.
   PubMed Web of Science ®Google Scholar
• OMURA, T. AND SATO, R., 1964, The carbon monoxide-binding pigment of liver microsomes. Journal of Biological Chemistry, 239, 2370–2378.
   PubMed Web of Science ®Google Scholar
• PARKER, L. N. AND ODELL, W. D., 1980, Control of adrenal androgen secretion. Endocrine Reviews, 1, 392–410.
   PubMedGoogle Scholar
• SHIMADA, T., MISONO, K. S. AND GUENGERICH, F. P., 1986, Human liver microsomal cytochrome P-450 mephenytoin 4-hydroxylase, a prototype of genetic polymorphism in oxidative drug metabolism. Journal of Biological Chemistry, 261, 909–921.
   PubMed Web of Science ®Google Scholar
• SHIRAGA, T., IWASAKI, K., NOZAKI, K., TAMURA, T., YAMAZOE, Y., KATO, R. AND TAKANAKA, A., 1994, Isolation and characterization of four cytochrome P450 isozymes from untreated and pheno-barbital-treated beagle dogs. Biological and Pharmaceutical Bulletin, 17, 22–28.
   PubMed Web of Science ®Google Scholar
• SWANECK, G. AND FISHMAN . J., 1988, Covalent binding of the endogenous estrogen 16a-hydroxyestrone to estradiol receptor in human breast cancer cells: characterization and intranuclear localization. Proceedings of National Academy of Sciences, USA., 85, 7831–7835.
   Google Scholar
• SWINNEY, D. C., RYAN, D. E., THOMAS, P. E. AND LEVIN, W., 1987, Regioselective progesterone hydroxylation catalyzed by eleven rat hepatic cytochrome P-450 isozymes. Biochemistry, 26, 7073–7083.
   PubMed Web of Science ®Google Scholar
• TELANG, NT., S UTO, A., WONG, G. Y., OSBORNE, M. P. AND BRADLOW, H. L., 1992, Induction by estrogen metabolite 16a-hydroxyestrone of genotoxic damage and aberrant proliferation in mouse mammary epithelial cells. Journal of the National Cancer Institute, 84, 634–638.
   PubMedGoogle Scholar
• WAXMAN, D. J., 1996, Role of metabolism in the activation of dehydroepiandrosterone as a peroxisome proliferator. Journal of Endocrinology, 150, S129–147.
   PubMedGoogle Scholar
• WAXMAN, D. J., Ko, A. AND WALSH, C., 1983, Regioselectivity and stereoselectivity of androgen hydroxylations catalyzed by cytochrome P-450 isozymes purified from phenobarbital-induced rat liver. Journal of Biological Chemistry, 258, 11937–11947.
   PubMed Web of Science ®Google Scholar