17β-Estradiol metabolism by hamster hepatic microsomes: Implications for the catechol-O-methyl transferase-mediated detoxication of catechol estrogens

Drug Metabolism and Disposition

Volumn 24, Issue 5, 1996, Pages 588-594

  Butterworth, Michael ^a   Lau, Serrine S ^a   Monks, Terrence J ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 HYDROXYESTRONE; ASCORBIC ACID; CATECHOL ESTROGEN; CATECHOL METHYLTRANSFERASE; DRUG METABOLITE; ESTRADIOL; ESTRIOL; ESTRONE; GLUTATHIONE; OXYGENASE;

ANIMAL TISSUE; ARTICLE; CARCINOGENICITY; CONTROLLED STUDY; DETOXIFICATION; DOSE RESPONSE; DRUG DISPOSITION; ENZYME ACTIVITY; ENZYME SUBSTRATE; ESTROGEN METABOLISM; KIDNEY CARCINOMA; LIVER MICROSOME; MALE; NONHUMAN; PRIORITY JOURNAL; SYRIAN HAMSTER;

ANIMALS; ASCORBIC ACID; CATECHOL O-METHYLTRANSFERASE; CRICETINAE; ESTRADIOL; ESTROGENS, CATECHOL; GLUTATHIONE; MAGNESIUM; MALE; MESOCRICETUS; METABOLIC DETOXICATION, DRUG; METHYLATION; MICROSOMES, LIVER; S-ADENOSYLMETHIONINE; STEROID 16-ALPHA-HYDROXYLASE;

ANIMALIA; CRICETINAE; MESOCRICETUS AURATUS;

EID: 0029862601     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (42)

1. J. G. Liehr and D. Roy: Free radical generation of cycling estrogens. Free Radic. Biol. Med. 8, 415-423 (1990).
2. V. S. Matthews, H. Kirkman, and R. L. Bacon: Kidney damage in the golden hamster following chronic administration of diethylstilbestrol and sesame oil. Proc. Soc. Exp. Biol. Med. 66, 195-196 (1947).
3. H. Kirkman and R. L. Bacon: Estrogen-induced tumors of the kidney. I. Incidence of renal tumors in intact and gonadectomized male golden hamster treated with diethylstilbestrol. J. Natl. Cancer Inst. 13, 745-755 (1952).
4. H. Kirkman: Estrogen-induced rumors of the kidney. III. Growth characteristics in the Syrian hamster. Natl. Cancer Inst. Monogr. 1, 1-57 (1959).
5. J. J. Li and S. A. Li: Estrogen carcinogenesis in hamster tissue. A critical review. Endocr. Rev. 11, 524-531 (1990).
6. J. G. Liehr: 2-Fluoroestradiol: separation of estrogenicity from carcinogenicity. Mol. Pharmacol. 23, 278-281 (1983).
7. J. G. Liehr, R. Deodutta, A. Ari-Ulubelen, Q. D. Bui, J. Weisz, and H. W. Strobel: Effect of chronic estrogen treatment of Syrian hamsters on microsomal enzymes mediating formation of catechol estrogens and their redox cycling: implications for carcinogenesis. J. Steroid Biochem. 35, 555-560 (1990).
8. J. Weisz, Q. D. Bui, R. Deodutta, and J. G. Liehr: Elevated 4-hydroxylation of estradiol by hamster kidney microsomes: a potential pathway of metabolic activation of estrogens. Endocrinology 131, 655-661 (1992).
9. P. Ball, H. P. Gelbke, and R. Knuppen: The excretion of 2-hydroxyestrone during the menstrual cycle. J. Clin. Endocrinol. Metab. 40, 406-408 (1975).
10. J. G. Williams, C. Longcope, and K. I. H. Williams: 4-Hydroxyestrone: a new metabolite of estradiol-17β from humans. Steroids 24, 687-701 (1974).
11. P. Ball, M. Haupt, and R. Knuppen: Comparative studies on the metabo-lism of estradiol in the brain, the pituitary and the liver of the rat. Acta Endocrinol. 87, 1-11 (1978).
12. P. Ball and R. Knuppen: Formation of 2- and 4-hydroxyestrogens by brain, pituitary and the liver of the human fetus. J. Clin. Endocrinol. Metab. 47, 732-737 (1978).
13. 450 monooxygenase. Endocrinology 101, 1604-1610 (1977).
14. S. A. Li, J. K. Klicka, and J. J. Li: Estrogen 2-4-hydroxylase activity and catechol estrogen formation in the hamster kidney: implications for estrogen carcinogenesis. Cancer Res. 45, 181-185 (1985).
15. H. Haaf, S. A. Li, and J. J. Li: Covalent binding of estrogen metabolites to hamster liver microsomal proteins: Inhibition by ascorbic acid and catechol-O-methyl transferase. Carcinogenesis 8, 209-215 (1987).
16. C. P. Martucci and J. Fishman: P450 enzymes of estrogen metabolism. Pharmacol. Ther. 57, 237-257 (1993).
17. M. T. Smith, C. G. Evans, H. Thor, and S. Orrenius: Quinone-induced oxidative injury to cells and tissues. In "Oxidative Stress" (H. Sies, ed.), pp. 91-113. Academic Press, London, 1985.
18. P. C. Jocelyn: "Biochemistry of the SH Group." Academic Press, London, 1972.
19. O. H. Lowry, N. J. Rosebrough, A. L. Farr, and R. J. Randall: Protein measurement with Folin phenol reagent. J. Biol. Chem. 193, 265-275 (1951).
20. C. R. Creveling and J. W. Daly: Assay of enzymes of catecholamine biosynthesis and metabolism. In "Methods of Biochemical Analysis of Biogenic Amines and Their Related Enzymes" (D. Glick, ed.), pp. 153-182. John Wiley & Sons, New York, 1971.
21. B. T. Zhu, D. Roy, and J. G. Liehr: The carcinogenic activity of ethinyl estrogens is determined by both their hormonal characteristics and their conversion to catechol metabolites. Endocrinology 132, 577-583 (1993).
22. B. T. Zhu and J. G. Liehr: Inhibition of the catechol-O-methyltransferase-catalyzed O-methylation of 2- and 4-hydroxyestradiol by catecholamines: implications for the mechanism of estrogen-induced carcinogenesis. Arch. Biochem. Biophys. 304, 248-256 (1993).
23. S. I. Li, R. H. Purdy, and S. L. Li: Variations in catechol O-methyl transferase activity in rodent tissues: Possible role in estrogen carcinogenicity. Carcinogenesis 10, 63-67 (1989).
24. P. Ball and R. Knuppen: Catecholestrogens (2 and 4-hydroxyestrogens): chemistry, biogenesis, metabolism, occurrence and physiological significance. Acta Endocrinol. (Suppl.) 232, 1-127 (1980).
25. J. Axelrod and R. Tomchick: Enzymatic O-methylation of epinephrine and other catechols. J. Biol. Chem. 233, 702-705 (1958).
26. B. Kalyanaraman and R. C. Sealy: Electron spin resonance-spin stabilization in enzymatic systems: detection of semiquinones produced during peroxidatic oxidation of catechols and catecholamines. Biochem. Biophys. Res. Commun. 106, 1119-1125 (1982).
27. S. D. Nelson, J. R. Mitchell, E. Dybing, and H. A. Sasame: Cytochrome P-450-mediated oxidation of 2-hydroxyestrogens to reactive intermediates. Biochem. Biophys. Res. Commun. 70, 1157-1165 (1976).
28. P. H. Jellinck, E. F. Hahn, and J. Fishman: Absence of reactive intermediates in the formation of catechol estrogens by rat liver microsomes. J. Biol. Chem. 261, 7729-7732 (1986).
29. E. Blaschke and G. Hertting: Enzymic methylation of L-ascorbic acid by catechol O-methyl-transferease. Biochem. Pharmacol. 20, 1363-1370 (1971).
30. D. R. Thakker and C. R. Creveling: O-Methylation. In "Conjugation Reactions in Drug Metabolism" (G. J. Mulder, ed.). pp 193-232. Taylor and Francis, London, 1990.
31. R. W. Brueggemeier, J. G. Kimball, and F. Kraft: Estrogen metabolism in rat liver microsomal and isolated hepatocyte preparations. II. Inhibition studies. J. Steroid Biochem. 21, 709-716 (1984).
32. F. Marks and E. Hecker: Metabolism and mechanism of action of estrogens. XII. Structure and mechanism of formation of water-soluble and protein-bound metabolites of estrone in rat liver microsomes in vitro and in vivo. Biochim. Biophys. Acta 187, 250-265 (1969).
33. E. Kuss: Water-soluble metabolites of oestradiol-17β. III. Separation and identification of 1- and 4-glutathione thioethers of 2,3-dihydroxy-oestratrienes. Hoppe-Seyler's Z. Physiol. Chem. 350, 95-97 (1969).
34. E. Kuss: Microsomal oxidation of estradiol-17β. 2-Hydroxylation and 1-or 4-thioether formation with and without 17-hydroxyl debydrogenation. Hoppe-Seyler's Z. Physiol. Chem. 352, 817-836 (1971).
35. J. S. Elce: Metabolism of a glutathione conjugate of 2-hydroxyoestradiol by rat liver and kidney preparations in vitro. Biochem. J. 116, 913-917 (1970).
36. J. S. Elce and J. Harris: Conjugation of 2-hydroxy-estradiol-17β [1,3,5,(10)-estratriene-2,3,17β-triol] with glutathione in the rat. Steroids 18, 583-591 (1971).
37. J. S. Elce: Metabolism of a glutathione conjugate of 2-hydroxyoestradiol17β in the adult male rat. Biochem. J. 126, 1067-1071 (1972).
38. J. S. Elce and J. Chandra: Estrogen mercapturic acids in the adult male rat Steroids 22, 699-705 (1973).
39. H.-O. Hoppen, L. Siekmann, and H. Breuer: Metabolism of oestrone in the microsomal fraction of rat liver. Hoppe-Seyler's Z. Physiol. Chem. 355, 1305-1315 (1974).
40. D. Roy, Q. D. Bui, J. Weisz, and J. G. Liehr: Comparison of assays for catechol estrogen synthase activity: product isolation verses radioenzymatic catechol-O-methyl-transferase-coupled procedures. J. Steroid Biochem. 33, 243-249 (1989).
41. A. C. Stalford, J. L. Maggs, T. L. Gilchrist, and B. K. Park: Carecholestrogens as mediators of carcinogenesis: correlation of aromatic hydroxylation of estradiol and its fluorinated analogs with tumor induction in Syrian hamsters. Mol. Pharmacol. 45, 1259-1267 (1994).
42. P. Ball, M. Haupt, and R. Knuppen: Biogenesis and metabolism of catechol estrogens in vitro. In "Catechol Estrogens" (G. R. Merriam and M. B. Lipsett, eds.), pp. 91-103. Raven Press, New York, 1983.