Carcinogenesis, Vol 19, 1-27, Copyright © 1998 by Oxford University Press
BT Zhu and AH Conney
Cytochrome P450 enzymes that metabolize estrogens are expressed in the
mammary gland, uterus, brain and other target tissues for estrogen action,
and this results in the formation of hydroxylated estrogens in these
tissues. Estradiol metabolites formed in target tissues at or near estrogen
receptors may either be inactive or have important biological effects, and
changes in the activities of estrogen- metabolizing enzymes in target
tissues may profoundly influence estrogen action. Although some active
estrogen metabolites exert hormonal effects in target tissues by
interaction with the classical estrogen receptor, other metabolites appear
to elicit unique biological responses that are not associated with
activation of this receptor. Therefore, some of the many actions of
estradiol may not be caused by estradiol per se, but may result from the
formation of active estrogen metabolite(s) which function as local
mediators or may activate their own unique receptors or effectors. This is
an important area in need of more research. The present paper represents a
review of the literature and perspectives by the authors on the functional
role of estrogen metabolism in target tissues.
REVIEWS
Functional role of estrogen metabolism in target cells: review and perspectives
Department of Chemical Biology, College of Pharmacy, Rutgers-The State University of New Jersey, Piscataway 08854-8020, USA.
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 A. M. Samuni, E. Y. Chuang, M. C. Krishna, W. Stein, W. DeGraff, A. Russo, and J. B. Mitchell Semiquinone radical intermediate in catecholic estrogen-mediated cytotoxicity and mutagenesis: Chemoprevention strategies with antioxidants PNAS, April 29, 2003; 100(9): 5390 - 5395. [Abstract] [Full Text] [PDF]
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 O. Barbier, L. Villeneuve, V. Bocher, C. Fontaine, I. P. Torra, C. Duhem, V. Kosykh, J.-C. Fruchart, C. Guillemette, and B. Staels The UDP-glucuronosyltransferase 1A9 Enzyme Is a Peroxisome Proliferator-activated Receptor alpha and gamma Target Gene J. Biol. Chem., April 11, 2003; 278(16): 13975 - 13983. [Abstract] [Full Text] [PDF]
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F. F. Kadlubar, G. S. Berkowitz, R. R. Delongchamp, C. Wang, B. L. Green, G. Tang, J. Lamba, E. Schuetz, and M. S. Wolff The CYP3A4*1B Variant Is Related to the Onset of Puberty, A Known Risk Factor for the Development of Breast Cancer Cancer Epidemiol. Biomarkers Prev., April 1, 2003; 12(4): 327 - 331. [Abstract] [Full Text] [PDF]
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J. D. Sibonga, S. Lotinun, G. L. Evans, V. S. Pribluda, S. J. Green, and R. T. Turner Dose-Response Effects of 2-Methoxyestradiol on Estrogen Target Tissues in the Ovariectomized Rat Endocrinology, March 1, 2003; 144(3): 785 - 792. [Abstract] [Full Text] [PDF]
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 R. K. Dubey, D. G. Gillespie, L. C. Zacharia, F. Barchiesi, B. Imthurn, and E. K. Jackson CYP450- and COMT-Derived Estradiol Metabolites Inhibit Activity of Human Coronary Artery SMCs Hypertension, March 1, 2003; 41(3): 807 - 813. [Abstract] [Full Text] [PDF]
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 T. H. Rasmussen, T. K. Andreassen, S. N. Pedersen, L. T. M. Van der Ven, P. Bjerregaard, and B. Korsgaard Effects of waterborne exposure of octylphenol and oestrogen on pregnant viviparous eelpout (Zoarces viviparus) and her embryos in ovario J. Exp. Biol., December 15, 2002; 205(24): 3857 - 3876. [Abstract] [Full Text] [PDF]
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S. M. Lippman and W. K. Hong Cancer Prevention Science and Practice Cancer Res., September 15, 2002; 62(18): 5119 - 5125. [Full Text] [PDF]
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S. Mesia-Vela, R. I. Sanchez, J. J. Li, S. A. Li, A. H. Conney, and F. C. Kauffman Catechol estrogen formation in liver microsomes from female ACI and Sprague-Dawley rats: comparison of 2- and 4-hydroxylation revisited Carcinogenesis, August 1, 2002; 23(8): 1369 - 1372. [Abstract] [Full Text] [PDF]
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T. M. LaVallee, X. H. Zhan, C. J. Herbstritt, E. C. Kough, S. J. Green, and V. S. Pribluda 2-Methoxyestradiol Inhibits Proliferation and Induces Apoptosis Independently of Estrogen Receptors {alpha} and {beta} Cancer Res., July 1, 2002; 62(13): 3691 - 3697. [Abstract] [Full Text] [PDF]
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E. I. O. Garner, E. E. Stokes, R. S. Berkowitz, S. C. Mok, and D. W. Cramer Polymorphisms of the Estrogen-metabolizing Genes CYP17 and Catechol-O-methyltransferase and Risk of Epithelial Ovarian Cancer Cancer Res., June 1, 2002; 62(11): 3058 - 3062. [Abstract] [Full Text] [PDF]
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F. Barchiesi, E. K. Jackson, D. G. Gillespie, L. C. Zacharia, J. Fingerle, and R. K. Dubey Methoxyestradiols Mediate Estradiol-Induced Antimitogenesis in Human Aortic SMCs Hypertension, April 1, 2002; 39(4): 874 - 879. [Abstract] [Full Text] [PDF]
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A. J. Lee, L. H. Mills, J. W. Kosh, A. H. Conney, and B. T. Zhu NADPH-Dependent Metabolism of Estrone by Human Liver Microsomes J. Pharmacol. Exp. Ther., March 1, 2002; 300(3): 838 - 849. [Abstract] [Full Text] [PDF]
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E. L. Cavalieri, P. Devanesan, M. C. Bosland, A. F. Badawi, and E. G. Rogan Catechol estrogen metabolites and conjugates in different regions of the prostate of Noble rats treated with 4-hydroxyestradiol: implications for estrogen-induced initiation of prostate cancer Carcinogenesis, February 1, 2002; 23(2): 329 - 333. [Abstract] [Full Text] [PDF]
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R. K. Dubey, D. G. Gillespie, L. C. Zacharia, M. Rosselli, B. Imthurn, and E. K. Jackson Methoxyestradiols Mediate the Antimitogenic Effects of Locally Applied Estradiol on Cardiac Fibroblast Growth Hypertension, February 1, 2002; 39(2): 412 - 417. [Abstract] [Full Text] [PDF]
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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]
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T. Hagenlocher, J. Nair, N. Becker, A. Korfmann, and H. Bartsch Influence of Dietary Fatty Acid, Vegetable, and Vitamin Intake on Etheno-DNA Adducts in White Blood Cells of Healthy Female Volunteers: A Pilot Study Cancer Epidemiol. Biomarkers Prev., November 1, 2001; 10(11): 1187 - 1191. [Abstract] [Full Text] [PDF]
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M. J. Messina and C. L. Loprinzi Soy for Breast Cancer Survivors: A Critical Review of the Literature J. Nutr., November 1, 2001; 131(11): 3095S - 3108. [Abstract] [Full Text] [PDF]
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 R. K. Dubey and E. K. Jackson Genome and Hormones: Gender Differences in Physiology: Invited Review: Cardiovascular protective effects of 17{beta}-estradiol metabolites J Appl Physiol, October 1, 2001; 91(4): 1868 - 1883. [Abstract] [Full Text] [PDF]
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J. A. Lavigne, J. E. Goodman, T. Fonong, S. Odwin, P. He, D. W. Roberts, and J. D. Yager The Effects of Catechol-O-Methyltransferase Inhibition on Estrogen Metabolite and Oxidative DNA Damage Levels in Estradiol-treated MCF-7 Cells Cancer Res., October 1, 2001; 61(20): 7488 - 7494. [Abstract] [Full Text] [PDF]
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J. E. Goodman, J. A. Lavigne, K. Wu, K. J. Helzlsouer, P. T. Strickland, J. Selhub, and J. D. Yager COMT genotype, micronutrients in the folate metabolic pathway and breast cancer risk Carcinogenesis, October 1, 2001; 22(10): 1661 - 1665. [Abstract] [Full Text] [PDF]
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E. Yagi, J.C. Barrett, and T. Tsutsui The ability of four catechol estrogens of 17{beta}-estradiol and estrone to induce DNA adducts in Syrian hamster embryo fibroblasts Carcinogenesis, September 1, 2001; 22(9): 1505 - 1510. [Abstract] [Full Text] [PDF]
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A. J. Lee, J. W. Kosh, A. H. Conney, and B. T. Zhu Characterization of the NADPH-Dependent Metabolism of 17beta -Estradiol to Multiple Metabolites by Human Liver Microsomes and Selectively Expressed Human Cytochrome P450 3A4 and 3A5 J. Pharmacol. Exp. Ther., August 1, 2001; 298(2): 420 - 432. [Abstract] [Full Text] [PDF]
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L. H. Mills, A. J. Lee, A. F. Parlow, and B. T. Zhu Preferential Growth Stimulation of Mammary Glands over Uterine Endometrium in Female Rats by a Naturally Occurring Estradiol-17{beta}-fatty Acid Ester Cancer Res., August 1, 2001; 61(15): 5764 - 5770. [Abstract] [Full Text] [PDF]
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V. K. Turan, V. M. Mishin, and P. E. Thomas Clotrimazole is a Selective and Potent Inhibitor of Rat Cytochrome P450 3A Subfamily-Related Testosterone Metabolism Drug Metab. Dispos., June 1, 2001; 29(6): 837 - 842. [Abstract] [Full Text]
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K. Mitrunen, N. Jourenkova, V. Kataja, M. Eskelinen, V.-M. Kosma, S. Benhamou, D. Kang, H. Vainio, M. Uusitupa, and A. Hirvonen Polymorphic Catechol-O-methyltransferase Gene and Breast Cancer Risk Cancer Epidemiol. Biomarkers Prev., June 1, 2001; 10(6): 635 - 640. [Abstract] [Full Text] [PDF]
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R. Todorovic, P. Devanesan, S. Higginbotham, J. Zhao, M. L. Gross, E. G. Rogan, and E. L. Cavalieri Analysis of potential biomarkers of estrogen-initiated cancer in the urine of Syrian golden hamsters treated with 4-hydroxyestradiol Carcinogenesis, June 1, 2001; 22(6): 905 - 911. [Abstract] [Full Text] [PDF]
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R. Elsby, J. L. Maggs, J. Ashby, D. Paton, J. P. Sumpter, and B. K. Park Assessment of the Effects of Metabolism on the Estrogenic Activity of Xenoestrogens: A Two-Stage Approach Coupling Human Liver Microsomes and a Yeast Estrogenicity Assay J. Pharmacol. Exp. Ther., April 13, 2001; 296(2): 329 - 337. [Abstract] [Full Text]
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H. Yamazaki, T. Komatsu, K. Takemoto, M. Saeki, Y. Minami, Y. Kawaguchi, N. Shimada, M. Nakajima, and T. Yokoi Decreases in Phenytoin Hydroxylation Activities Catalyzed by Liver Microsomal Cytochrome P450 Enzymes in Phenytoin-Treated Rats Drug Metab. Dispos., April 1, 2001; 29(4): 427 - 434. [Abstract] [Full Text]
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M. T. Goodman, K. McDuffie, L. N. Kolonel, K. Terada, T. A. Donlon, L. R. Wilkens, C. Guo, and L. Le Marchand Case-Control Study of Ovarian Cancer and Polymorphisms in Genes Involved in Catecholestrogen Formation and Metabolism Cancer Epidemiol. Biomarkers Prev., March 1, 2001; 10(3): 209 - 216. [Abstract] [Full Text]
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W. Zheng, F. Jin, L. A. Dunning, X.-O. Shu, Q. Dai, W.-Q. Wen, Y.-T. Gao, and J. L. Holtzman Epidemiological Study of Urinary 6{beta}-Hydroxycortisol to Cortisol Ratios and Breast Cancer Risk Cancer Epidemiol. Biomarkers Prev., March 1, 2001; 10(3): 237 - 242. [Abstract] [Full Text]
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P. Devanesan, R. Todorovic, J. Zhao, M. L. Gross, E. G. Rogan, and E. L. Cavalieri Catechol estrogen conjugates and DNA adducts in the kidney of male Syrian golden hamsters treated with 4-hydroxyestradiol: potential biomarkers for estrogen-initiated cancer Carcinogenesis, March 1, 2001; 22(3): 489 - 497. [Abstract] [Full Text] [PDF]
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 R. Clarke, F. Leonessa, J. N. Welch, and T. C. Skaar Cellular and Molecular Pharmacology of Antiestrogen Action and Resistance Pharmacol. Rev., March 1, 2001; 53(1): 25 - 72. [Abstract] [Full Text] [PDF]
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