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

Chemical Research in Toxicology

Volumn 14, Issue 12, 2001, Pages 1654-1659

  Zhang, F ^a   Swanson, S M ^a   Van Breemen, R B ^a   Liu, X ^a   Yang, Y ^a   Gu, C ^a   Bolton, J L ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXYEQUILENIN; 4 HYDROXYESTRONE; CARCINOGEN; CATECHOL DERIVATIVE; CONJUGATED ESTROGEN; DEOXYADENOSINE; DEOXYGUANOSINE; DEOXYRIBONUCLEOTIDE; DNA; EQUILENIN; EQUILIN; ESTROGEN DERIVATIVE; ESTRONE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; APURINIC SITE; ARTICLE; BREAST CANCER; CANCER RISK; CONTROLLED STUDY; DNA ADDUCT; DNA ALKYLATION; DNA DAMAGE; DNA STRAND BREAKAGE; DOSE RESPONSE; DRUG DNA BINDING; ESTROGEN METABOLISM; FEMALE; HORMONE BINDING; HORSE; HYDROLYSIS; MASS SPECTROMETRY; MOLECULAR STABILITY; NONHUMAN; OXIDATION; RAT;

ANIMALS; BREAST; COMET ASSAY; DEOXYADENOSINES; DEOXYGUANOSINE; DNA ADDUCTS; DNA DAMAGE; DNA, SINGLE-STRANDED; DOSE-RESPONSE RELATIONSHIP, DRUG; EQUILENIN; ESTRADIOL CONGENERS; FEMALE; GUANINE; OXIDATION-REDUCTION; QUINONES; RATS; RATS, SPRAGUE-DAWLEY;

ANIMALIA; EQUIDAE; EQUUS CABALLUS;

EID: 0035659961     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx010158c     Document Type: Article

References (46)

1. Hormonal treatment of postmenopausal women
2. Effects of hormone therapy on bone mineral density: Results from the postmenopausal estrogen/progestin interventions (PEPI) trial
3. Postmenopausal estrogen and progestin use and the risk of cardiovascular disease
4. Hormone therapy to prevent disease and prolong life in postmenopausal women
5. Hormone replacement therapy and risk of breast cancer with a favorable histology: Results of the Iowa Women's Health Study
6. Estrogens as a cause of human cancer: The Richard and Hinda Rosenthal foundation award lecture
7. Estrogens and breast cancer
8. Genotoxic effects of estrogens
9. The use of estrogens and progestins and the risk of breast cancer in postmenopausal women
10. New role for estrogen in cancer?
11. Role of quinoids in estrogen carcinogenesis
12. Molecular mechanisms of estrogen carcinogenesis
13. Functional role of estrogen metabolism in target cells: Review and perspectives
14. Characterization of DNA damage induced by 3,4-estrone-o-quinone in human cells
15. DNA damage caused by reactive oxygen species originating from a copper-dependent oxidation of the 2-hydroxy catechol of estradiol
16. DNA damage induced by catecholestrogens in the presence of copper (II): Generation of reactive oxygen species and enhancement by NADH
17. Microsome-mediated 8-hydroxylation of guanine bases of DNA by steroid estrogens: Correlation of DNA damage by free radicals with metabolic activation to quinones
18. Relative rates of 2- and 4-hydroxyestrogen synthesis are dependent on both substrate and tissue
19. Carcinogenic activities of various steroidal and nonsteroidal estrogens in the hamster kidney: Relation to hormonal activity and cell proliferation
20. Mechanism of cytochrome P450-catalyzed aromatic hydroxylation of estrogens
21. Bioreductive activation of catechol estrogen-ortho-quinones: Aromatization of the B ring in 4-hydroxyequilenin markedly alters quinoid formation and reactivity
22. Inhibition of glutathione S-transferase activity by the quinoid metabolites of equine estrogens
23. The major metabolite of equilin, 4-hydroxyequilin autoxidizes to an o-quinone which isomerizes to the potent cytotoxin 4-hydroxyequilenin-o-quinone
24. A metabolite of equine estrogens, 4-hydroxyequilenin, induces DNA damage and apoptosis in breast cancer cell lines
25. Evidence that a metabolite of equine estrogens, 4-hydroxyequilenin, induces cellular transformation in vitro
26. Reaction of the Premarin metabolite 4-hydroxyequilenin semiquinone radical with 2′-deoxyguanosine: Formation of unusual cyclic adducts
27. Alkylation of 2′-deoxynucleosides and DNA by the Premarin metabolite 4-hydroxyequilenin semiquinone radical
28. Comparison of negative and positive ion electrospray tandem mass spectrometry for the liquid chromatography tandem mass spectrometry analysis of oxidized deoxynucleosides
29. The equine estrogen metabolite 4-hydroxyequilenin causes DNA single- strand breaks and oxidation of DNA bases in vitro
30. Molecular origin of cancer: Catechol estrogen-3,4,-quinones as endogenous tumor initiators
31. Heterogeneity in radiation-induced DNA damage and repair in tumor and normal cells measured using the comet assay
32. A simple technique for quantitation of low levels of DNA damage in individual cells
33. The role of adduct site-specific mutagenesis in understanding how carcinogen-DNA adducts cause mutations: Perspective, prospects, and problems
34. What structual features determine repair enzyme specificity and mechanism in chemically modified DNA?
35. Role of DNA adducts in hormonal carcinogenesis
36. Estrogen-induced endogenous DNA adduction: Possible mechanism of hormonal cancer
37. Localization of estrogen-induced DNA adducts and cytochrome P-450 activity at the site of renal carcinogenesis in the hamster kidney
38. Induction of a DNA adduct detectable by 32P-postlabeling in the dorsolateral prostate of NBL/Cr rats treated with estradiol-17 beta and testosterone
39. Relating aromatic hydrocarbon-induced DNA adducts and c-H-ras mutations in mouse skin papillomas: The role of apurinic sites
40. Urinary 8-hydroxy-2′-deoxyguanosine as a biological marker of in vivo oxidative DNA damage
41. 8-Hydroxydeoxyguanosine and 8-hydroxyguanine as biomarkers of oxidative DNA damage
42. Levels of 8-hydroxydeoxyguanosine as a marker of DNA damage in human leukocytes
43. p-quinone methides are the major decomposition products of catechol estrogen o-quinones
44. Protective effect of estrogens and catecholestrogens against peroxidative membrane damage in vitro
45. Catechol estrogens are more potent antioxidants than estrogens for the Cu(2+)-catalyzed oxidation of low or high-density lipoprotein: Antioxidative effects of steroids on lipoproteins