Alkylation of 2'-deoxynucleosides and DNA by the premarin metabolite 4- hydroxyequilenin semiquinone radical

Chemical Research in Toxicology

Volumn 11, Issue 2, 1998, Pages 94-101

  Shen, Li ^a   Qiu, Shengxiang ^a   Chen, Yumei ^a   Zhang, Fagen ^a   Van Breemen, Richard B ^a   Nikolic, Dejan ^a   Bolton, Judy L ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2' DEOXYNUCLEOSIDE; CONJUGATED ESTROGEN; DEOXYADENOSINE; DEOXYCYTIDINE PHOSPHATE; DEOXYGUANOSINE; DNA; DRUG METABOLITE; EQUILENIN; RADICAL; SEMIQUINONE;

APURINIC SITE; ARTICLE; DNA ADDUCT; DNA ALKYLATION; DNA DAMAGE; DRUG CARCINOGENICITY; ESTROGEN THERAPY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION;

ALKYLATION; CARCINOGENS; CYTOSINE; DEOXYADENOSINES; DEOXYGUANOSINE; DNA; DNA ADDUCTS; DNA DAMAGE; EQUILENIN; ESTROGENS, CONJUGATED (USP); FREE RADICALS; HUMANS; OXIDATIVE STRESS;

EID: 0031931940     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx970181r     Document Type: Article

References (41)

1. Henderson, B. E., Ross, R., and Bernstein, L. (1988) Estrogens as a cause of human cancer: The Richard and Hinda Rosenthal Foundation Award Lecture. Cancer Res. 48, 246-253.
2. Feigelson, H. S., and Henderson, B. E. (1996) Estrogens and breast cancer. Carcinogenesis 17, 2279-2284.
3. Liehr, J. G. (1990) Genotoxic effects of estrogens. Mutat. Res. 238, 269-276.
4. 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.
5. 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. N. Engl. J. Med. 332, 1589-1593.
6. Harris, R. B., Laws, A., Reddy, F. M., King, A., and Haskell, W. L. (1990) Are women using postmenopausal estrogens? A community survey. Am. J. Public Health 80, 1266-1268.
7. 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. N. EngL J. Med. 336, 1769-1775.
8. Lobo, R. A. (1995) Benefits and risks of estrogen replacement therapy. Am. J. Obstet Gynecol. 173, 982-989.
9. Paganinihill, A. (1995) Estrogen replacement therapy and stroke. Prog. Cardiovasc. Diseases 38, 223-242.
10. Wickelgren, I. (1997) Estrogen: A new weapon against Alzheimer's. Science 276, 676-677.
11. Henderson, V. W. (1997) The epidemiology of estrogen replacement therapy and Alzheimer's disease. Neurology 48, S27-S35.
12. Martucci, C. P., and Fishman, J. (1993) P450 enzymes of estrogen metabolism. Pharmacol. Ther. 57, 237-257.
13. Yager, J. D., and Liehr, J. G. (1996) Molecular mechanisms of estrogen carcinogenesis. Annu. Rev. Pharmacol. ToxicoL 36, 203- 232.
14. Nutter, L. M., Ngo, E. O., and Abul-Hajj, Y. J. (1991) Characterization of DNA damage induced by 3,4-estrone-o-quinone in human cells. J. Biol. Chem. 266, 16380-16386.
15. Musarrat, J., Arezina-Wilson, J., and Wani, A. A. (1996) Prognostic and aetiological relevance of 8-hydroxyguanosine in human breast carcinogenesis. Eur. J. Cancer 32A, 1209-1214.
16. Abul-Hajj, Y. J., Tabakovic, K., and Tabakovic, I. (1995) An estrogen-nucleic acid adduct. Electroreductive intermolecular coupling of 3,4-estrone-o-quinone and adenine. J. Am. Chem. Soc. 117, 6144-6145.
17. Stack, D. E., Byun, J., Gross, M. L., Rogan, E. G., and Cavalieri, E. L. (1996) Molecular characteristics of catechol estrogen quinones in reactions with deoxyribonucleosides. Chem. Res. Toxicol. 9, 851-859.
18. Akanni, A., Tabakovic, K., and Abul-Hajj, Y. J. (1997) Estrogennucleic acid adducts: Reaction of 3,4-estrone-o-quinone with nucleic acid bases. Chem. Res. Toxicol. 10, 477-481.
19. Akanni, A., and Abul-Hajj, Y. J. (1997) Estrogen-nucleic acid adducts: Reaction of 3,4-estrone-o-quinone radical anion with deoxynucleosides. Chem. Res. Toxicol. 10, 760-766.
20. Dwivedy, I., Devanesan, P., Cremonesi, P., Rogan, E., and Cavalieri, E. (1992) Synthesis and characterization of estrogen 2,3- and 3,4-quinones. Comparison of DNA adducts formed by the quinones versus horseradish peroxidase-activated catechol estrogens. Chem. Res. Toxicol. 5, 828-833.
21. 32P-postlabeling in the dorsolateral prostrate of NBL/Cr rats treated with estradiol-17β and testosterone. Carcinogenesis 16, 951-954.
22. Purdy, R. H., Moore, P. H., Williams, M. C., Goldzheher, H. W., and Paul, S. M. (1982) Relative rates of 2- and 4-hydroxyestrogen synthesis are dependent on both substrate and tissue. FEBS Lett. 138, 40-44.
23. 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.
24. Sarrabia, S. F., Zhu, B. T., Kurosawa, T., Tohma, M., and Liehr, J. G. (1997) Mechanism of cytochrome P450-catalyzed aromatic hydroxylation of estrogens. Chem. Res. Toxicol. 10, 767-771.
25. 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.
26. Han, X., and Liehr, J. G. (1995) Microsome-mediated 8-hydroxylation of guanine bases of DNA by steroid estrogens: Correlation of DNA damage by free radicals with metabolic activation to quinones. Carcinogenesis 16, 2571-2574.
27. NIH. (1981) NIH Guidelines for the Laboratory Use of Chemical Carcinogens, NIH Publication No. 81-2385, U.S. Government Printing Office, Washington, DC.
28. Teuber, H. J. (1953) Reaktionen mit nitrosodisulfonat (III). Equilenin-chinon. Chem. Ber. 86, 1495-1499.
29. Gehrke, C. W., McCune, R. A., and Kenneth, C. K. (1984) Quantitative reversed-phase high-performance liquid chromatography of major and modified nucleosides in DNA. J. Chromatogr. 301, 199-219.
30. Lewis, M. A., Yoerg-Graff, D., Bolton, J. L., and Thompson, J. A. (1996) Alkylation of 2'-deoxynucleosides and DNA by quinone methides derived from 2,6-di-tert-butyl-4-methylphenol. Chem. Res. Toxicol. 9, 1368-1374.
31. Shen, L., Qiu, S., van Breemen, R. B., Zhang, F., Chen, Y., and Bolton, J. L. (1997) Reaction of the Premarin metabolite 4-hydroxyequilenin semiquinone radical with 2'-deoxyguanosine: Formation of unusual cyclic adducts. J. Am. Chem. Soc. 119, 11126- 11127.
32. Klaassen, C. D. (1996) Casarett & Doull's Toxicology: The Basic Science of Poisons, McGraw Hill, New York, NY.
33. Singer, B., and Hang, B. (1997) What structual features determine repair enzyme specificity and mechanism in chemically modified DNA? Chem. Res. Toxicol. 10, 713-732.
34. Liehr, J. G., Avitts, T. A., Randerath, E., and Randerath, K. (1986) Estrogen-induced endogenous DNA adduction: Possible mechanism of hormonal cancer. Proc. Natl. Acad. Sci. U.S.A. 83, 5301- 5305.
35. Liehr, J. G., Hall, E. R., Avitts, T. A., Randerath, E., and Randerath, K. (1987) Localization of estrogen-induced DNA adducts and cytochrome P450 activity at the site of renal carcinogenesis in the hamster kidney. Cancer Res. 47, 2156-2159.
36. Loeb, L. A., and Preston, B. D. (1986) Mutagenesis by apurinic/ apyrimidinic sites. Annu. Rev. Genet. 20, 201-203.
37. Liehr, J. G., Fang, W. R., Sirbasku, D. A., and Ari-Ulubelen, A. (1986) Carcinogenicity of catechol estrogens in Syrian hamsters. J. Steroid Biochem. 24, 353-356.
38. Li, Y., Trush, M. A., and Yager, J. D. (1994) DNA damage caused by reactive oxygen species originating from a copper-dependent oxidation of the 2-hydroxy catechol of estradiol. Carcinogenesis 15, 1421-1427.
39. Zady, M. F., and Wong, J. L. (1980) Unusual competition between nitrogen and carbon methylation of nucleosides by methyl radical in various aqueous media. J. Am. Chem. Soc. 45, 2373-2377.
40. 3H] 17β-dihydroequilin sulfate in normal postmenopausal women. Steroids 59, 389-394.
41. Ikegawa, S., Itoh, M., and Goto, J. (1994) Separatory determination of biliary metabolites of equilin in rat by high-performance liquid chromatography. J. Liq. Chromatogr. 17, 223-239.