Effect of halogenated substituents on the metabolism and estrogenic effects of the equine estrogen, equilenin

Chemical Research in Toxicology

Volumn 16, Issue 6, 2003, Pages 741-749

  Liu, Xuemei ^a   Zhang, Fagen ^a   Liu, Hong ^a   Burdette, Joanna E ^a   Li, Yan ^a   Overk, Cassia R ^a   Pisha, Emily ^a   Yao, Jiaqin ^a   Van Breemen, Richard B ^a   Swanson, Steven M ^a   Bolton, Judy L ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

17BETA EQUILENIN; 17BETA HYDROXY 4 BROMOEQUILENIN; 17BETA HYDROXY 4 CHLOROEQUILENIN; 17BETA HYDROXY 4 FLUOROEQUILENIN; 17BETA HYDROXY 5 FLUOROEQUILENIN; 17BETA HYDROXYEQUILENIN; 17BETA HYDROXYEQUILENIN DERIVATIVE; 4 BROMOEQUILENIN; 4 CHLOROEQUILENIN; 4 FLUOROEQUILENIN; 4 FLUOROEQUILENIN DERIVATIVE; 4 HYDROXYEQUILENIN; ALKALINE PHOSPHATASE; CATECHOL DERIVATIVE; CONJUGATED ESTROGEN; DNA; EQUILENIN; EQUILENIN DERIVATIVE; EQUILIN; ESTRADIOL; ESTROGEN; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; FUNCTIONAL GROUP; GLUTATHIONE; HALIDE; MONOPHENOL MONOOXYGENASE; PROTEIN PS2; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; AUTOOXIDATION; BINDING AFFINITY; BREAST CANCER; BREAST DEVELOPMENT; CELL DIFFERENTIATION; CYTOTOXICITY; DNA ALKYLATION; DNA DAMAGE; DRUG RECEPTOR BINDING; ENDOMETRIUM CANCER; ENZYME INDUCTION; ESTROGEN ACTIVITY; ESTROGEN METABOLISM; ESTROGEN SYNTHESIS; ESTROGEN THERAPY; FEMALE; GENE INDUCTION; HORMONAL CARCINOGENESIS; HUMAN; HUMAN CELL; METABOLITE; NONHUMAN; OXIDATION; OXIDATION REDUCTION REACTION; PROTEIN EXPRESSION; RAT; UTERUS GROWTH; VAGINA;

EQUIDAE;

EID: 10744226193     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx030001f     Document Type: Article

References (46)

1. Vogel, V. G., Yeomeans, A., and Higginbotham, E. (1993) Clinical management of women at increased risk for breast cancer. Breast Cancer Res. Treat. 28, 195-210.
2. Service, R. F. (1998) New role for estrogen in cancer? Science 279, 1631-1633.
3. Colditz, G. A., Hankinson, S. E., Hunter, D. J., Willett, W. C., Manson, J. E., Stampfer, M. J., Hennekens, C., Rosner, B., and Speizer, F. E. (1995) The use of estrogens and progestins and the risk of breast cancer in postmenopausal women. New Engl. J. Med. 332, 1589-1593.
4. Grodstein, F., Stampfer, M. J., Colditz, G. A., Willett, W. C., Manson, J. E., Joffe, M., Rosner, B., Fuchs, C., Hankinson, S. E., Hunter, D. J., Hennekens, C. H., and Speizer, F. E. (1997) Postmenopausal hormone therapy and mortality. New Engl. J. Med. 336, 1769-1775.
5. Lupulescu, A. (1995) Estrogen Use and Cancer Incidence: A Review. Cancer Invest. 13, 287-295.
6. Bolton, J. L., Pisha, E., Zhang, F., and Qiu, S. (1998) Role of quinoids in estrogen carcinogenesis. Chem. Res. Toxicol. 11, 1113-1127.
7. Zumoff, B. (1998) Does postmenopausal estrogen administration increase the risk of breast cancer? Contributions of animal, biochemical, and clinical investigative studies to a resolution of the controversy. Proc. Soc. Exp. Biol. Med. 217, 30-37.
8. Steinberg, K. K., Smith, S. J., Thacker, S. B., and Stroup, D. F. (1994) Breast cancer risk and duration of estrogen use - The role of study design in meta-analysis. Epidemiology 5, 415-421.
9. Liehr, J. G., Stancel, G. M., Chorich, L. P., Bousfield, G. R., and Ulubelen, A. A. (1986) Hormonal carcinogenesis: separation of estrogenicity from carcinogenicity. Chem.-Biol. Interact. 59, 173-184.
10. Liehr, J. G. (2000) Is estradiol a genotoxic mutagenic carcinogen? Endocr. Rev. 21, 40-54.
11. Li, J. J., Li, S. A., Oberley, T. D., and Parsons, J. A. (1995) Carcinogenic activities of various steroidal and nonsteroidal estrogens in the hamster kidney: relation to hormonal activity and cell proliferation. Cancer Res. 55, 4347-4351.
12. Klaunig, J. E., Xu, Y., Isenberg, J. S., Bachowski, S., Kolaja, K. L., Jiang, J., Stevenson, D. E., and Walborg, E. F. (1998) The role of oxidative stress in chemical carcinogenesis. Environ. Health Perspect. 106 S1, 289-295.
13. Chen, Y., Shen, L., Zhang, F., Lau, S. S., van Breemen, R. B., Nikolic, D., and Bolton, J. L. (1998) The equine estrogen metabolite 4-hydroxyequilenin causes DNA single-strand breaks and oxidation of DNA bases in vitro. Chem. Res. Toxicol. 11, 1105-1111.
14. Zhang, F., Chen, Y., Pisha, E., Shen, L., Xiong, Y., van Breemen, R. B., and Bolton, J. L. (1999) The major metabolite of equilin, 4-hydroxyequilin autoxidizes to an o-quinone which isomerizes to the potent cytotoxin 4-hydroxyequilenin-o-quinone. Chem. Res. Toxicol. 12, 204-213.
15. Shen, L., Pisha, E., Huang, Z., Pezzuto, J. M., Krol, E., Alam, Z., van Breemen, R. B., and Bolton, J. L. (1997) Bioreductive activation of catechol estrogen-ortho-quinones: Aromatization of the B ring in 4-hydroxyequilenin markedly alters quinoid formation and reactivity. Carcinogenesis 18, 1093-1101.
16. Zhang, F., Swanson, S. M., van Breemen, R. B., Liu, X., Yang, Y., Gu, C., and Bolton, J. L. (2001) Equine estrogen metabolite 4-hydroxyequilenin induces DNA damage in the rat mammary tissues: formation of single-strand breaks, apurinic sites, stable adducts, and oxidized bases. Chem. Res. Toxicol. 14, 1654-1659.
17. Marnett, L. J. (2000) Oxyradicals and DNA damage. Carcinogenesis 21, 361-370.
18. Cavalieri, E. L., Stack, D. E., Devanesan, P. D., Todorovic, R., Dwivedy, I., Higginbotham, S., Johansson, S. L., Patil, K. D., Gross, M. L., Gooden, J. K., Ramanathan, R., Cerny, R. L., and Rogan, E. G. (1997) Molecular origin of cancer: Catechol estrogen-3,4-quinones as endogenous tumor initiators. Proc. Natl. Acad. Sci. U.S.A. 94, 10937-10942.
19. Pisha, E., Liu, X., Constantinou, A. I., and Bolton, J. L. (2001) Evidence that a metabolite of equine estrogens, 4-hydroxyequilenin, induces cellular transformation in vitro. Chem. Res. Toxicol. 14, 82-90.
20. Liehr, J. G. (1983) 2-Fluoroestradiol. Separation of Estrogenicity from Carcinogenicity. Mol. Pharmacol. 23, 278-281.
21. NIH Guidelines for the Laboratory Use of Chemical Carcinogens. U.S. Government Printing Office, Washington, DC, 1981.
22. Hylarides, M. D., Wilbur, D. S., and Mettler, F. A. (1983) B-ring aromatization of estrogen derivatives. Steroids 41, 657-662.
23. Spink, D. C., Zhang, F., Hussain, M. M., Katz, B. H., Liu, X., Hilker, D. R., and Bolton, J. L. (2001) Metabolism of equilenin in MCF-7 and MDA-MB-231 human breast cancer cells. Chem. Res. Toxicol. 14, 572-581.
24. Bachand, C., Driguez, H., Paton, J. M., Touchard, D., and Lessard, J. (1974) N-Monochlorination and N-Monobromination of Carbamates and Carboxamides by Sodium Hypochlorite and Hypobromite. J. Org. Chem. 39, 3136-3137.
25. Rao, P. N., and Somawardhana, C. W. (1987) Synthesis of 2-methoxy and 4-methoxy equine estrogens. Steroids 49, 419-432.
26. Chang, M., Zhang, F., Shen, L., Pauss, N., Alam, I., van Breemen, R. B., Blond-Elguindi, S., and Bolton, J. L. (1998) Inhibition of glutathione S-transferase activity by the quinoid metabolites of equine estrogens. Chem. Res. Toxicol. 11, 758-765.
27. Blair, R. M., Fang, H., Branham, W. S., Hass, B. S., Dial, S. L., Moland, C. L., Tong, W., Shi, L., Perkins, R., and Sheehan, D. M. (2000) The estrogen receptor relative binding affinities of 188 natural and xenochemicals: structural diversity of ligands. Toxicol. Sci. 54, 138-153.
28. Obourn, J. D., Koszewski, N. J., and Notides, A. C. (1993) Hormone- and DNA-binding mechanisms of the recombinant human estrogen receptor. Biochemistry 32, 6229-6236.
29. Liu, J., Burdette, J. E., Xu, H., Gu, C., van Breemen, R. B., Bhat, K. P., Booth, N., Constantinou, A. I., Pezzuto, J. M., Fong, H. H., Farnsworth, N. R., and Bolton, J. L. (2001) Evaluation of estrogenic activity of plant extracts for the potential treatment of menopausal symptoms. J. Agric. Food Chem. 49, 2472-2479.
30. Pisha, E., and Pezzuto, J. M. (1997) Cell-based assay for the determination of estrogenic and anti-estrogenic activities. Methods Cell Sci. 19, 37-43.
31. Sandoval, M., Zhang, X. J., Liu, X., Mannick, E. E., Clark, D. A., and Miller, M. J. (1997) Peroxynitrite-induced apoptosis in T84 and RAW 264.7 cells: attenuation by L-ascorbic acid. Free Radical Biol. Med. 22, 489-495.
32. Ciapetti, G., Granchi, D., Stea, S., Savarino, L., Verri, E., Gori, A., Savioli, F., and Montanaro, L. (1998) Cytotoxicity testing of materials with limited in vivo exposure is affected by the duration of cell-material contact. J. Biomed. Mater. Res. 42, 485-490.
33. Nakagawa, Y., and Tayama, K. (2002) Benzophenone-induced estrogenic potency in ovariectomized rats. Arch. Toxicol. 76, 727-731.
34. Burdette, J. E., Liu, J., Lantvit, D., Lim, E., Booth, N., Bhat, K. P., Hedayat, S., Van Breemen, R. B., Constantinou, A. I., Pezzuto, J. M., Farnsworth, N. R., and Bolton, J. L. (2002) Trifolium pratense (red clover) exhibits estrogenic effects in vivo in ovariectomized Sprague-Dawley rats. J. Nutr. 132, 27-30.
35. Wangen, K. E., Duncan, A. M., Merz-Demlow, B. E., Xu, X., Marcus, R., Phipps, W. R., and Kurzer, M. S. (2000) Effects of soy isoflavones on markers of bone turnover in premenopausal and postmenopausal women. J. Clin. Endocrinol. Metab. 85, 3043-3048.
36. Holinka, C. F., Hata, H., Kuramoto, H., and Gurpide, E. (1986) Effects of steroid hormones and antisteroids on alkaline phosphatase activity in human endometrial cancer cells (Ishikawa line). Cancer Res. 46, 2771-2774.
37. Albert, J. L., Sundstrom, S. A., and Lyttle, C. R. (1990) Estrogen regulation of placental alkaline phosphatase gene expression in a human endometrial adenocarcinoma cell line. Cancer Res. 50, 3306-3310.
38. Dehal, S. S., and Kupfer, D. (1996) Evidence that the catechol 3,4-dihydroxytamoxifen is a proximate intermediate to the reactive species binding covalently to proteins. Cancer Res. 56, 1283-1290.
39. Dehal, S. S., and Kupfer, D. (1999) Cytochrome P-450 3A and 2D6 catalyze ortho hydroxylation of 4-hydroxytamoxifen and 3-hydroxytamoxifen (droloxifene) yielding tamoxifen catechol: involvement of catechols in covalent binding to hepatic proteins. Drug Metab. Dispos. 27, 681-688.
40. Davidge, S. T., Zhang, Y., and Stewart, K. G. (2001) A comparison of ovariectomy models for estrogen studies. Am. J. Physiol. Regul. Integr. Comput. Physiol. 280, R904-R907.
41. Raynaud, J. P., Bouton, M. M., Gallet-Bourquin, D., Philibert, D., Tournemine, C., and Azadian-Baulanger, G. (1973) Comparative study of estrogen action. Mol. Pharmacol. 9, 520-533.
42. Morgan, P., Maggs, J. L., Bulman-Page, P. C., Hussain, F., and Park, B. K. (1992) The metabolism of 2- and 4-fluoro -17 beta-oestradiol in the rat and its implications for oestrogen carcinogenesis. Biochem. Pharmacol. 43, 985-993.
43. Liehr, J. G., Fang, W. F., Sirbasku, D. A., and Ari-Ulubelen, A. (1986) Carcinogenicity of catechol estrogens in Syrian hamsters. J. Steroid Biochem. 24, 353-356.
44. Knuppen, R., Ball, P., and Emons, G. (1986) Importance of A-ring substitution of estrogens for the physiology and pharmacology of reproduction. J. Steroid Biochem. 24, 193-198.
45. Kang, K. S., Kim, H. S., Ryu, D. Y., Che, J. H., and Lee, Y. S. (2000) Immature uterotrophic assay is more sensitive than ovariectomized uterotrophic assay for the detection of estrogenicity of p-nonylphenol in Sprague-Dawley rats. Toxicol. Lett. 118, 109-115.
46. Scobie, G. A., Macpherson, S., Millar, M. R., Groome, N. P., Romana, P. G., and Saunders, P. T. (2002) Human oestrogen receptors: differential expression of ERalpha and beta and the identification of ERbeta variants. Steroids 67, 985-992.