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Volumn 11, Issue 10, 1998, Pages 1113-1127

Role of quinoids in estrogen carcinogenesis

Author keywords

[No Author keywords available]

Indexed keywords

CATECHOL ESTROGEN; CONJUGATED ESTROGEN; CYTOCHROME P450 REDUCTASE; DNA; EQUILENIN; EQUILIN; ESTRADIOL; ESTROGEN; ESTRONE; GLUTATHIONE; QUINONE DERIVATIVE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE (PHOSPHATE) DEHYDROGENASE (QUINONE);

EID: 0031741669     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx9801007     Document Type: Review
Times cited : (193)

References (150)
  • 1
    • 0023836871 scopus 로고
    • Estrogens as a cause of human cancer: The Richard and Hinda Rosenthal Foundation Award Lecture
    • 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.
    • (1988) Cancer Res , vol.48 , pp. 246-253
    • Henderson, B.E.1    Ross, R.2    Bernstein, L.3
  • 3
    • 0025373464 scopus 로고
    • Genotoxic effects of estrogens
    • Liehr, J. G. (1990) Genotoxic effects of estrogens. Mutat. Res. 238, 269-276.
    • (1990) Mutat. Res. , vol.238 , pp. 269-276
    • Liehr, J.G.1
  • 4
    • 0026331038 scopus 로고
    • Toward the primary prevention of cancer
    • Henderson, B. E., ROSS, R. K., and Pike, M. C. (1991) Toward the primary prevention of cancer. Science 254, 1131-1138.
    • (1991) Science , vol.254 , pp. 1131-1138
    • Henderson, B.E.1    Ross, R.K.2    Pike, M.C.3
  • 5
    • 0032513345 scopus 로고    scopus 로고
    • New role for estrogen in cancer?
    • Service, R. F. (1998) New role for estrogen in cancer? Science 279, 1631-1633.
    • (1998) Science , vol.279 , pp. 1631-1633
    • Service, R.F.1
  • 6
    • 0026578966 scopus 로고
    • Nuclear receptors and chemical carcinogenesis
    • Green, S. (1992) Nuclear receptors and chemical carcinogenesis. Trends Pharmacol. Sci. 13, 251-255.
    • (1992) Trends Pharmacol. Sci. , vol.13 , pp. 251-255
    • Green, S.1
  • 7
    • 0029890377 scopus 로고    scopus 로고
    • Molecular mechanisms of estrogen carcinogenesis
    • Yager, J. D., and Liehr, J. G. (1996) Molecular mechanisms of estrogen carcinogenesis. Annu. Rev. Pharmacol. Toxicol. 36, 203-232.
    • (1996) Annu. Rev. Pharmacol. Toxicol. , vol.36 , pp. 203-232
    • Yager, J.D.1    Liehr, J.G.2
  • 8
    • 0031848636 scopus 로고    scopus 로고
    • Functional role of estrogen metabolism in target cells: Review and perspectives
    • Zhu, B. T., and Conney, A. H. (1998) Functional role of estrogen metabolism in target cells: review and perspectives. Carcinogenesis 19, 1-27.
    • (1998) Carcinogenesis , vol.19 , pp. 1-27
    • Zhu, B.T.1    Conney, A.H.2
  • 10
    • 0020631150 scopus 로고
    • 2-Fluoroestradiol. Separation of Estrogenicity from Carcinogenicity
    • Liehr, J. G. (1983) 2-Fluoroestradiol. Separation of Estrogenicity from Carcinogenicity. Mol, Pharmacol. 23, 278-281.
    • (1983) Mol, Pharmacol. , vol.23 , pp. 278-281
    • Liehr, J.G.1
  • 11
    • 0021235133 scopus 로고
    • Estrogen-induced tumorigenesis in hamsters: Roles for hormonal and carcinogenic activities
    • Li, J. J., and Li, S. A. (1984) Estrogen-induced tumorigenesis in hamsters: Roles for hormonal and carcinogenic activities. Arch. Toxicol. 55, 110-118.
    • (1984) Arch. Toxicol. , vol.55 , pp. 110-118
    • Li, J.J.1    Li, S.A.2
  • 12
    • 0025052917 scopus 로고
    • Molecular mechanisms of oxygen radical carcinogenesis and mutagenesis. the role of DNA base damage
    • Breimer, L. H. (1990) Molecular mechanisms of oxygen radical carcinogenesis and mutagenesis. The role of DNA base damage. Mol. Carcinog. 3, 188-197.
    • (1990) Mol. Carcinog. , vol.3 , pp. 188-197
    • Breimer, L.H.1
  • 13
    • 0027717574 scopus 로고
    • Estrogen replacement therapy in women at increased risk for breast cancer
    • Vassilopoulou-Sellin, R. (1993) Estrogen replacement therapy in women at increased risk for breast cancer. Breast Cancer Res. Treat. 28, 167-177.
    • (1993) Breast Cancer Res. Treat. , vol.28 , pp. 167-177
    • Vassilopoulou-Sellin, R.1
  • 14
    • 0029018399 scopus 로고
    • Estrogen Use and Cancer Incidence: A Review
    • Lupulescu, A. (1995) Estrogen Use and Cancer Incidence: A Review. Cancer Invest. 13, 287-295.
    • (1995) Cancer Invest , vol.13 , pp. 287-295
    • Lupulescu, A.1
  • 15
    • 0029071008 scopus 로고
    • Hormone-Replacement Therapy-Breast Versus Heart Versus Bone
    • Davidson, N. E. (1995) Hormone-Replacement Therapy-Breast Versus Heart Versus Bone. N. Engl. J. Med. 332, 1638-1639.
    • (1995) N. Engl. J. Med. , vol.332 , pp. 1638-1639
    • Davidson, N.E.1
  • 16
    • 0031983773 scopus 로고    scopus 로고
    • Does postmenopausal estrogen administration increase the risk of breast cancer? Contributions of animal, biochemical, and clinical investigative studies to a resolution of the controversy
    • Zurnoff, 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.
    • (1998) Proc. Soc. Exp. Biol. Med. , vol.217 , pp. 30-37
    • Zurnoff, B.1
  • 18
    • 0028306005 scopus 로고
    • Breast cancer risk and duration of estrogen use: The role of study design in meta-analysis
    • 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.
    • (1994) Epidemiology , vol.5 , pp. 415-421
    • Steinberg, K.K.1    Smith, S.J.2    Thacker, S.B.3    Stroup, D.F.4
  • 21
    • 0028895128 scopus 로고
    • Estrogen replacement therapy and stroke
    • Paganinihill, A. (1995) Estrogen replacement therapy and stroke. Prog. Cardiovasc. Dis. 38, 223-242.
    • (1995) Prog. Cardiovasc. Dis. , vol.38 , pp. 223-242
    • Paganinihill, A.1
  • 22
    • 0030911093 scopus 로고    scopus 로고
    • Estrogen: A new weapon against Alzheimer's
    • Wickelgren, I. (1997) Estrogen: A new weapon against Alzheimer's. Science 276, 676-677.
    • (1997) Science , vol.276 , pp. 676-677
    • Wickelgren, I.1
  • 23
    • 0030942682 scopus 로고    scopus 로고
    • The epidemiology of estrogen replacement therapy and Alzheimer's disease
    • Henderson, V. W. (1997) The epidemiology of estrogen replacement therapy and Alzheimer's disease. Neurology 48, S27-S35.
    • (1997) Neurology , vol.48
    • Henderson, V.W.1
  • 24
    • 0030856295 scopus 로고    scopus 로고
    • The effect of estrogen replacement therapy on cognitive function in women; A critical review of the literature
    • Haskell, S. G., Richardson, E. D., and Horwitz, R. I. (1997) The effect of estrogen replacement therapy on cognitive function in women; A critical review of the literature. J. Clin. Epidemiol. 50, 1249-1264.
    • (1997) J. Clin. Epidemiol. , vol.50 , pp. 1249-1264
    • Haskell, S.G.1    Richardson, E.D.2    Horwitz, R.I.3
  • 25
    • 0038126450 scopus 로고    scopus 로고
    • The top 200 drugs
    • February issue
    • American Druggist Merchandising (1996) The top 200 drugs. 18-20 (February issue).
    • (1996) American Druggist Merchandising , pp. 18-20
  • 26
    • 0029050292 scopus 로고
    • Carcinogenic activities of various steroidal and nonsteroidal estrogens in the hamster kidney: Relation to hormonal activity and cell proliferation
    • 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.
    • (1995) Cancer Res. , vol.55 , pp. 4347-4351
    • Li, J.J.1    Li, S.A.2    Oberley, T.D.3    Parsons, J.A.4
  • 28
    • 0020030701 scopus 로고
    • Assay for conjugated estrogens in tablets using fused-silica capillary gas chromatography
    • Lyman, G. W., and Johnson, R. N. (1982) Assay for conjugated estrogens in tablets using fused-silica capillary gas chromatography. J. Chromatogr. 234, 234-239.
    • (1982) J. Chromatogr. , vol.234 , pp. 234-239
    • Lyman, G.W.1    Johnson, R.N.2
  • 30
    • 0020655112 scopus 로고
    • Aromatic hydroxylation of estrogens
    • Fishman, J. (1983) Aromatic hydroxylation of estrogens. Annu. Rev. Physiol. 45, 61-72.
    • (1983) Annu. Rev. Physiol. , vol.45 , pp. 61-72
    • Fishman, J.1
  • 31
    • 0018853550 scopus 로고
    • Catecholoestrogens (2- And 4-Hydroxyoestrogens): Chemistry, Biogenesis, Metabolism, Occurrence and Physiological Significance
    • Ball, P., and Knuppen, R. (1980) Catecholoestrogens (2- and 4-Hydroxyoestrogens): Chemistry, Biogenesis, Metabolism, Occurrence and Physiological Significance. Acta Endocrinol., Suppl. 232, 1-127.
    • (1980) Acta Endocrinol. , vol.232 , Issue.SUPPL. , pp. 1-127
    • Ball, P.1    Knuppen, R.2
  • 32
    • 0022619793 scopus 로고
    • 17β-Estradiol 2- And 4-hydroxylation catalysed by rat hepatic cytochrome P450: Role of individual forms, inductive effects, developmental patterns, and alterations by gonadectomy and hormone replacement
    • Dannan, G. A., Porubek, D. J., Nelson, S. D., Waxman, D. J., and Guengerich, F. P. (1986) 17β-Estradiol 2- and 4-hydroxylation catalysed by rat hepatic cytochrome P450: role of individual forms, inductive effects, developmental patterns, and alterations by gonadectomy and hormone replacement. Endocrinology 118, 1952-1960.
    • (1986) Endocrinology , vol.118 , pp. 1952-1960
    • Dannan, G.A.1    Porubek, D.J.2    Nelson, S.D.3    Waxman, D.J.4    Guengerich, F.P.5
  • 33
    • 0030026898 scopus 로고    scopus 로고
    • Effects of phenobarbital, dexamethasone, and 3-methylcholanthrene administration on the metabolism of 17β-estradiol by liver microsomes from female rats
    • Suchar, L. A., Chang, R. L., Thomas, P. E., Rosen, R. T., Lech, J., and Conney, A. H. (1996) Effects of phenobarbital, dexamethasone, and 3-methylcholanthrene administration on the metabolism of 17β-estradiol by liver microsomes from female rats. Endocrinology 137, 663-676.
    • (1996) Endocrinology , vol.137 , pp. 663-676
    • Suchar, L.A.1    Chang, R.L.2    Thomas, P.E.3    Rosen, R.T.4    Lech, J.5    Conney, A.H.6
  • 34
    • 0023883363 scopus 로고
    • Oxidation of 17a-ethylestradiol by human liver cytochrome P450
    • Guengerich, F. P. (1988) Oxidation of 17a-ethylestradiol by human liver cytochrome P450. Mol. Pharmacol. 33, 500-508.
    • (1988) Mol. Pharmacol. , vol.33 , pp. 500-508
    • Guengerich, F.P.1
  • 35
    • 0027167145 scopus 로고
    • P450 enzymes of estrogen metabolism
    • Martucci, C. P., and Fishman, J. (1993) P450 enzymes of estrogen metabolism. Pharmacol. Ther. 57, 237-257.
    • (1993) Pharmacol. Ther. , vol.57 , pp. 237-257
    • Martucci, C.P.1    Fishman, J.2
  • 36
    • 0028574698 scopus 로고
    • The Effects of 2,3,7,8-Tetrachlorodibenzo-p-dioxin on Estrogen Metabolism in MCF-7 Breast Cancer Cells: Evidence for Induction of a Novel 17βEstradiol 4-Hydroxylase
    • Spink, D. C., Hayes, C. L., Young, N. R., Christou, M., Sutter, T. R., Jefcoate, C. R., and Gierthy, J. F. (1994) The Effects of 2,3,7,8-Tetrachlorodibenzo-p-dioxin on Estrogen Metabolism in MCF-7 Breast Cancer Cells: Evidence for Induction of a Novel 17βEstradiol 4-Hydroxylase. J. Steriod Biochem. Mol. Biol. 51, 251-258.
    • (1994) J. Steriod Biochem. Mol. Biol. , vol.51 , pp. 251-258
    • Spink, D.C.1    Hayes, C.L.2    Young, N.R.3    Christou, M.4    Sutter, T.R.5    Jefcoate, C.R.6    Gierthy, J.F.7
  • 38
  • 42
    • 78651128652 scopus 로고
    • Estrogen-induced tumors of the kidney III. Growth characteristics in the Syrian hamster
    • Kirkman, H. (1959) Estrogen-induced tumors of the kidney III. Growth characteristics in the Syrian hamster. Natl. Cancer Inst. Monogr. 1, 1-57.
    • (1959) Natl. Cancer Inst. Monogr. , vol.1 , pp. 1-57
    • Kirkman, H.1
  • 44
    • 0023181602 scopus 로고
    • Estrogen carcinogenesis in Syrian hamster tissues: Role of metabolism
    • Li, J. J., and Li, S. A. (1987) Estrogen carcinogenesis in Syrian hamster tissues: Role of metabolism. Fed. Proc. 46, 1858-1863.
    • (1987) Fed. Proc. , vol.46 , pp. 1858-1863
    • Li, J.J.1    Li, S.A.2
  • 45
    • 0030986245 scopus 로고    scopus 로고
    • Hormone-associated cancer: Mechanistic similarities between breast cancer and estrogen-induced kidney carcinogenesis in hamsters
    • Liehr, J. G. (1997) Hormone-associated cancer: Mechanistic similarities between breast cancer and estrogen-induced kidney carcinogenesis in hamsters. Environ. Health Perspect. 105 (S3), 565-569.
    • (1997) Environ. Health Perspect. , vol.105 , Issue.S3 , pp. 565-569
    • Liehr, J.G.1
  • 46
    • 0029865150 scopus 로고    scopus 로고
    • 4-Hydroxylation of estrogens as marker of human mammary tumors
    • Liehr, J. G., and Ricci, M. J. (1996) 4-Hydroxylation of estrogens as marker of human mammary tumors. Proc. Natl. Acad. Sci. U.S.A. 93, 3294-3296.
    • (1996) Proc. Natl. Acad. Sci. U.S.A. , vol.93 , pp. 3294-3296
    • Liehr, J.G.1    Ricci, M.J.2
  • 47
    • 0027366267 scopus 로고
    • Elevated estrogen 16α-hydroxylase activity: Is this a genotoxic or nongenotoxic biomarker in human breast cancer risk?
    • Nebert, D. W. (1993) Elevated estrogen 16α-hydroxylase activity: Is this a genotoxic or nongenotoxic biomarker in human breast cancer risk? J. Natl Cancer Inst. 85, 1888-1891.
    • (1993) J. Natl Cancer Inst. , vol.85 , pp. 1888-1891
    • Nebert, D.W.1
  • 48
    • 0024307660 scopus 로고
    • Binding of 2-hydroxyestradiol and 4-hydroxyestradiol to estrogen receptors from human breast cancers
    • van Aswegen, C. H., Purdy, R. H., and Wittliff, J. L. (1989) Binding of 2-hydroxyestradiol and 4-hydroxyestradiol to estrogen receptors from human breast cancers. J. Steroid Biochem. 32, 485-492.
    • (1989) J. Steroid Biochem. , vol.32 , pp. 485-492
    • Van Aswegen, C.H.1    Purdy, R.H.2    Wittliff, J.L.3
  • 49
    • 0343178292 scopus 로고
    • Covalent binding of the endogenous estrogen 16α-hydroxyestrone to estradil receptor in human breast cancer cells: Characterization and intranuclear localization
    • Swaneck, G. E., and Fishman, J. (1988) Covalent binding of the endogenous estrogen 16α-hydroxyestrone to estradil receptor in human breast cancer cells: Characterization and intranuclear localization. Proc. Natl. Acad. Sci. U.SA. 85, 7831-7835.
    • (1988) Proc. Natl. Acad. Sci. U.SA. , vol.85 , pp. 7831-7835
    • Swaneck, G.E.1    Fishman, J.2
  • 51
    • 0031936766 scopus 로고    scopus 로고
    • Estrogen metabolism and the malignant potential of human papillomavirus immortalized keratinocytes
    • Newfield, L., Bradlow, H. L., Sepkovic, D. W., and Auborn, K. (1998) Estrogen metabolism and the malignant potential of human papillomavirus immortalized keratinocytes. Proc. Soc. Exp. Biol Med. 217, 322-326.
    • (1998) Proc. Soc. Exp. Biol Med. , vol.217 , pp. 322-326
    • Newfield, L.1    Bradlow, H.L.2    Sepkovic, D.W.3    Auborn, K.4
  • 52
    • 0021270323 scopus 로고
    • Increased estrogen- 16α-hydroxylase activity in women with breast and endometrial cancer
    • Fishman, J., Schneider, J., and Hershcopf, R. J. (1984) Increased estrogen- 16α-hydroxylase activity in women with breast and endometrial cancer. J. Steroid Biochem. 20, 1077-1081.
    • (1984) J. Steroid Biochem. , vol.20 , pp. 1077-1081
    • Fishman, J.1    Schneider, J.2    Hershcopf, R.J.3
  • 53
    • 0024829749 scopus 로고
    • Diet and urinary estrogen profile determination in young Finnish vegetarian and omnivorous women
    • Adlercreutz, H., Fotsis, T., and Hockerstedt, K. (1989) Diet and urinary estrogen profile determination in young Finnish vegetarian and omnivorous women. J. Steroid Biochem. 34, 527-530.
    • (1989) J. Steroid Biochem. , vol.34 , pp. 527-530
    • Adlercreutz, H.1    Fotsis, T.2    Hockerstedt, K.3
  • 55
    • 0018627984 scopus 로고
    • Catecholestrogen synthesis and metabolism by human breast tumors in vitro
    • Huffman, A. R., Paul, S. M., and Axelrod, J. (1979) Catecholestrogen synthesis and metabolism by human breast tumors in vitro. Cancer Res. 39, 4584-4587.
    • (1979) Cancer Res , vol.39 , pp. 4584-4587
    • Huffman, A.R.1    Paul, S.M.2    Axelrod, J.3
  • 57
    • 0031430951 scopus 로고    scopus 로고
    • Decreased serum estradiol concentration associated with high dietary intake of soy products in premenopausal Japanese women
    • Nagata, C., Kabuto, M., Kurisu, Y., and Shimizu, H. (1997) Decreased serum estradiol concentration associated with high dietary intake of soy products in premenopausal Japanese women. Nutr. Cancer 29, 228-233.
    • (1997) Nutr. Cancer , vol.29 , pp. 228-233
    • Nagata, C.1    Kabuto, M.2    Kurisu, Y.3    Shimizu, H.4
  • 58
    • 0016571597 scopus 로고
    • Cancer epidemiology in populations of the United States with emphasis on Hawaii and California and Japan
    • Dunn, J. E. (1975) Cancer epidemiology in populations of the United States with emphasis on Hawaii and California and Japan. Cancer Res. 35, 3240-3245.
    • (1975) Cancer Res , vol.35 , pp. 3240-3245
    • Dunn, J.E.1
  • 59
    • 0020471249 scopus 로고
    • Relative rates of 2- And 4-hydroxyestrogen synthesis are dependent on both substrate and tissue
    • 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.
    • (1982) FEBS Lett , vol.138 , pp. 40-44
    • Purdy, R.H.1    Moore, P.H.2    Williams, M.C.3    Goldzheher, H.W.4    Paul, S.M.5
  • 60
    • 0021934592 scopus 로고
    • Estrogen 2- And 4-hydroxylase activity, catechol estrogen formation, and implications for estrogen carcinogenesis in the hamster kidney
    • Li, S. A., Klicka, J. K., and Li, J. J. (1985) Estrogen 2- and 4-hydroxylase activity, catechol estrogen formation, and implications for estrogen carcinogenesis in the hamster kidney. Cancer Res. 45, 181-185.
    • (1985) Cancer Res , vol.45 , pp. 181-185
    • Li, S.A.1    Klicka, J.K.2    Li, J.J.3
  • 61
    • 0343144815 scopus 로고    scopus 로고
    • Mechanism of cytochrome P450-catalyzed aromatic hydroxylation of estrogens
    • Sarabia, 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.
    • (1997) Chem. Res. Toxicol. , vol.10 , pp. 767-771
    • Sarabia, S.F.1    Zhu, B.T.2    Kurosawa, T.3    Tohma, M.4    Liehr, J.G.5
  • 62
    • 0031974053 scopus 로고    scopus 로고
    • Pharmacokinetics and pharmacodynamics of conjugated equine estrogens: Chemistry and metabolism
    • Bhavnani, B. R. (1998) Pharmacokinetics and pharmacodynamics of conjugated equine estrogens: Chemistry and metabolism. Proc. Soc. Exp. Biol. Med. 217, 6-16.
    • (1998) Proc. Soc. Exp. Biol. Med. , vol.217 , pp. 6-16
    • Bhavnani, B.R.1
  • 63
    • 0015577667 scopus 로고
    • A simple chemical method for the synthesis of catechol estrogens
    • Gelbke, H. P., Haupt, O., and Knuppen, R. (1973) A simple chemical method for the synthesis of catechol estrogens. Steroids 21, 205-217.
    • (1973) Steroids , vol.21 , pp. 205-217
    • Gelbke, H.P.1    Haupt, O.2    Knuppen, R.3
  • 64
    • 0031426130 scopus 로고    scopus 로고
    • Bioreductive activation of catechol estrogen-ortho-quinones: Aromatization of the B ring in 4-hydroxyequilenin markedly alters quinoid formation and reactivity
    • Shen, L., Pisha, E., Huang, Z., Pezzuto, J. M., Krol, E., Alain, 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.
    • (1997) Carcinogenesis , vol.18 , pp. 1093-1101
    • Shen, L.1    Pisha, E.2    Huang, Z.3    Pezzuto, J.M.4    Krol, E.5    Alain, Z.6    Van Breemen, R.B.7    Bolton, J.L.8
  • 65
    • 0023633331 scopus 로고
    • Synthesis of 2-methoxy and 4-methoxy equine estrogens
    • Rao, P. N., and Somawardhana, C. W. (1987) Synthesis of 2-methoxy and 4-methoxy equine estrogens. Steroids 49, 419-432.
    • (1987) Steroids , vol.49 , pp. 419-432
    • Rao, P.N.1    Somawardhana, C.W.2
  • 66
    • 0026426696 scopus 로고
    • Molecular mechanisms for mammalian melanogenesis: Comparison with insect cuticular sclerotization
    • Sugumaran, M. (1991) Molecular mechanisms for mammalian melanogenesis: Comparison with insect cuticular sclerotization. FEBS Lett. 293, 233-239.
    • (1991) FEBS Lett , vol.293 , pp. 233-239
    • Sugumaran, M.1
  • 67
    • 0026040838 scopus 로고
    • Molecular mechanisms of quinone cytotoxicity
    • O'Brien, P. J. (1991) Molecular mechanisms of quinone cytotoxicity. Chem.-Biol. Interact. 80, 1-14.
    • (1991) Chem.-Biol. Interact. , vol.80 , pp. 1-14
    • O'Brien, P.J.1
  • 68
    • 0028301879 scopus 로고
    • Catechol estrogen production in rat microsomes after treatment with indole-3-carbinol, ascorbigen, or β-naphthaflavone; A comparison of stable isotope dilution gas chromatography-mass spectrometry and radiometric methods
    • Sepkovic, D. W., Bradlow, H. L., Michnovicz, J., Murtezani, S., Levy, I., and Osborne, M. P. (1994) Catechol estrogen production in rat microsomes after treatment with indole-3-carbinol, ascorbigen, or β-naphthaflavone; A comparison of stable isotope dilution gas chromatography-mass spectrometry and radiometric methods. Steroids 59, 318-323.
    • (1994) Steroids , vol.59 , pp. 318-323
    • Sepkovic, D.W.1    Bradlow, H.L.2    Michnovicz, J.3    Murtezani, S.4    Levy, I.5    Osborne, M.P.6
  • 69
    • 0020471249 scopus 로고
    • Relative rates of 2- And 4-hydroxyestrogen synthesis are dependent on both substrate and tissue
    • 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.
    • (1982) FEBS Lett , vol.138 , pp. 40-44
    • Purdy, R.H.1    Moore, P.H.2    Williams, M.C.3    Goldzheher, H.W.4    Paul, S.M.5
  • 70
    • 0029894354 scopus 로고    scopus 로고
    • 17β-Estradiol metabolism by hamster hepatic microsomes; Comparison of catechol estrogen O-methylation with catechol estrogen oxidation and glutathione conjugation
    • Butter-worth, M., Lau, S. S., and Monks, T. J. (1996) 17β-Estradiol metabolism by hamster hepatic microsomes; Comparison of catechol estrogen O-methylation with catechol estrogen oxidation and glutathione conjugation. Chem. Res. Toxicol. 9, 793-799.
    • (1996) Chem. Res. Toxicol. , vol.9 , pp. 793-799
    • Butter-worth, M.1    Lau, S.S.2    Monks, T.J.3
  • 71
    • 0029924611 scopus 로고    scopus 로고
    • Bioactivation of estrone and its catechol metabolites to quinoidglutathione conjugates in rat liver microsomes
    • Iverson, S. L., Shen, L., Anlar, N., and Bolton, J. L. (1996) Bioactivation of estrone and its catechol metabolites to quinoidglutathione conjugates in rat liver microsomes. Chem. Res. Toxicol. 9, 492-499.
    • (1996) Chem. Res. Toxicol. , vol.9 , pp. 492-499
    • Iverson, S.L.1    Shen, L.2    Anlar, N.3    Bolton, J.L.4
  • 72
    • 0031417558 scopus 로고    scopus 로고
    • Formation of catechol estrogen glutathione conjugates and gamma-glutamyl transpeptidase-dependent nephrotoxicity of 17-β-estradiol in the golden Syrian hamster
    • Butterworth, M., Lau, S. S., and Monks, T. J. (1997) Formation of catechol estrogen glutathione conjugates and gamma-glutamyl transpeptidase-dependent nephrotoxicity of 17-β-estradiol in the golden Syrian hamster. Carcinogenesis 18, 561-567.
    • (1997) Carcinogenesis , vol.18 , pp. 561-567
    • Butterworth, M.1    Lau, S.S.2    Monks, T.J.3
  • 73
    • 0018639798 scopus 로고
    • Synthesis, redox characteristics, and in vitro norepinephrine uptake inhibiting properties of 2-(2-mercapto-4,5-dihydroxyphenyl)ethylamine (6-mercaptodopamine)
    • Chardarian, C. G., and Castagnoli, N. (1979) Synthesis, redox characteristics, and in vitro norepinephrine uptake inhibiting properties of 2-(2-mercapto-4,5-dihydroxyphenyl)ethylamine (6-mercaptodopamine). J. Med. Chem. 22, 1317-1322.
    • (1979) J. Med. Chem. , vol.22 , pp. 1317-1322
    • Chardarian, C.G.1    Castagnoli, N.2
  • 74
    • 0017711733 scopus 로고
    • A new mechanism of in vitro formation of catechol estrogen glutathione conjugates by rat liver microsomes
    • Numazawa, M., and Nambara, T. (1977) A new mechanism of in vitro formation of catechol estrogen glutathione conjugates by rat liver microsomes. J. Steroid Biochem. 8, 835-840.
    • (1977) J. Steroid Biochem. , vol.8 , pp. 835-840
    • Numazawa, M.1    Nambara, T.2
  • 75
    • 0022904104 scopus 로고
    • Regioselective reaction of thiols with catechol estrogens and estrogen-o-quinones
    • Abul-Hajj, Y. J., and Cisek, P. L. (1986) Regioselective reaction of thiols with catechol estrogens and estrogen-o-quinones. J. Steroid Biochem. 25, 245-247.
    • (1986) J. Steroid Biochem. , vol.25 , pp. 245-247
    • Abul-Hajj, Y.J.1    Cisek, P.L.2
  • 77
    • 0012934592 scopus 로고
    • Base-catalyzed oxygenation of 3,5-Di-tert-butylpyrocatechol and its related compounds
    • Nishinaga, A., Itahara, T., and Matsuura, T. (1974) Base-catalyzed oxygenation of 3,5-Di-tert-butylpyrocatechol and its related compounds. Bull. Chem. Soc. Jpn. 47, 1811-1812.
    • (1974) Bull. Chem. Soc. Jpn. , vol.47 , pp. 1811-1812
    • Nishinaga, A.1    Itahara, T.2    Matsuura, T.3
  • 78
    • 0028353636 scopus 로고
    • Dual effect of cyclodextrins on catechol autoxidation
    • Eliseev, A. V., and Yatsimirskii, A. K. (1994) Dual effect of cyclodextrins on catechol autoxidation. J. Org. Chem. 59, 264-265.
    • (1994) J. Org. Chem. , vol.59 , pp. 264-265
    • Eliseev, A.V.1    Yatsimirskii, A.K.2
  • 79
    • 0023907050 scopus 로고
    • Spectroscopic identification of ortho-quinones as the products of polycyclic aromatic trans-dihydrodiol oxidation catalyzed by dihydrodiol dehydrogenase
    • Smithgall, T. E., Harvey, R. G., and Penning, T. M. (1988) Spectroscopic identification of ortho-quinones as the products of polycyclic aromatic trans-dihydrodiol oxidation catalyzed by dihydrodiol dehydrogenase. J. Biol. Chem. 263, 1814-1820.
    • (1988) J. Biol. Chem. , vol.263 , pp. 1814-1820
    • Smithgall, T.E.1    Harvey, R.G.2    Penning, T.M.3
  • 80
    • 0027363349 scopus 로고
    • Dihydrodiol dehydrogenase and its role in polycyclic aromatic hydrocarbon metabolism
    • Penning, T. M. (1993) Dihydrodiol dehydrogenase and its role in polycyclic aromatic hydrocarbon metabolism. Chem.-Biol. Interact. 89, 1-34.
    • (1993) Chem.-Biol. Interact. , vol.89 , pp. 1-34
    • Penning, T.M.1
  • 82
    • 0029949969 scopus 로고    scopus 로고
    • P-Quinone methides are the major decomposition products of catechol estrogen o-quinones
    • Bolton, J. L., and Shen, L. (1996) p-Quinone methides are the major decomposition products of catechol estrogen o-quinones. Carcinogenesis 17, 925-929.
    • (1996) Carcinogenesis , vol.17 , pp. 925-929
    • Bolton, J.L.1    Shen, L.2
  • 83
    • 0024600031 scopus 로고
    • Variations in catechol O-methyltransferase activity in rodent tissues: Possible role in estrogen carcinogenicity
    • Li, S. A., Purdy, R. H., and Li, J. J. (1989) Variations in catechol O-methyltransferase activity in rodent tissues: possible role in estrogen carcinogenicity. Carcinogenesis 10, 63-67.
    • (1989) Carcinogenesis , vol.10 , pp. 63-67
    • Li, S.A.1    Purdy, R.H.2    Li, J.J.3
  • 84
    • 0028285123 scopus 로고
    • Evidence that 4-allyl-ortho-quinones spontaneously rearrange to their more electrophilic quinone methides: Potential bioactivation mechanism for the hepatocarcinogen safrole
    • Bolton, J. L., Acay, N. M., and Vukomanovic, V. (1994) Evidence that 4-allyl-ortho-quinones spontaneously rearrange to their more electrophilic quinone methides: Potential bioactivation mechanism for the hepatocarcinogen safrole. Chem. Res. Toxicol. 7, 443-450.
    • (1994) Chem. Res. Toxicol. , vol.7 , pp. 443-450
    • Bolton, J.L.1    Acay, N.M.2    Vukomanovic, V.3
  • 85
    • 0029061720 scopus 로고
    • The influence of the para-alkyl substituent on the isomerization of o-quinones to p-quinone methides: Potential bioactivation mechanism for catechols
    • Iverson, S. L., Hu, L. Q., Vukomanovic, V., and Bolton, J. L. (1995) The influence of the para-alkyl substituent on the isomerization of o-quinones to p-quinone methides: Potential bioactivation mechanism for catechols. Chem. Res. Toxicol. 8, 537-544.
    • (1995) Chem. Res. Toxicol. , vol.8 , pp. 537-544
    • Iverson, S.L.1    Hu, L.Q.2    Vukomanovic, V.3    Bolton, J.L.4
  • 86
    • 0030034847 scopus 로고    scopus 로고
    • The mechanism of isomerization of 4-propyl-o-quinone to its tautomeric p-quinone methide
    • Bolton, J. L., Wu, H. M., and Hu, L. Q. (1996) The mechanism of isomerization of 4-propyl-o-quinone to its tautomeric p-quinone methide. Chem. Res. Toxicol. 9, 109-113.
    • (1996) Chem. Res. Toxicol. , vol.9 , pp. 109-113
    • Bolton, J.L.1    Wu, H.M.2    Hu, L.Q.3
  • 87
    • 0027175404 scopus 로고
    • Estradiolinduced effects on glutathione metabolism in rat hepatocytes
    • Ruiz, L. M., Garrido, M. J., and Lacort, M. (1993) Estradiolinduced effects on glutathione metabolism in rat hepatocytes. J. Biochem. (Tokyo) 113, 563-567.
    • (1993) J. Biochem. (Tokyo) , vol.113 , pp. 563-567
    • Ruiz, L.M.1    Garrido, M.J.2    Lacort, M.3
  • 88
    • 3142560550 scopus 로고
    • Biological implications of the nucleophilic addition of glutathione to quinoid compounds
    • Vina, J., Ed. CRC Press, Boca Raton, FL
    • Brunmark, A., and Cadenas, E. (1990) Biological implications of the nucleophilic addition of glutathione to quinoid compounds. In Glutathione: Metabolism and physiological functions (Vina, J., Ed.) pp 279-294, CRC Press, Boca Raton, FL.
    • (1990) Glutathione: Metabolism and Physiological Functions , pp. 279-294
    • Brunmark, A.1    Cadenas, E.2
  • 89
    • 0027102766 scopus 로고
    • Toxicology of quinonethioethers
    • Monks, T. J., and Lau, S. S. (1992) Toxicology of quinonethioethers. Crit. Rev. Toxicol. 22, 243-270.
    • (1992) Crit. Rev. Toxicol. , vol.22 , pp. 243-270
    • Monks, T.J.1    Lau, S.S.2
  • 90
    • 0031446380 scopus 로고    scopus 로고
    • Biological reactivity of polyphenolic glutathione conjugates
    • Monks, T. J., and Lau, S. S. (1997) Biological reactivity of polyphenolic glutathione conjugates. Chem. Res. Toxicol. 10, 1296-1313.
    • (1997) Chem. Res. Toxicol. , vol.10 , pp. 1296-1313
    • Monks, T.J.1    Lau, S.S.2
  • 91
    • 0023836435 scopus 로고
    • The Biooxidation of Cytotoxic Ellipticine Derivatives: A Key to Structure-Activity Relationship Studies?
    • Meunier, G., De Montauzon, D., Bernadou, J., Grassy, G., Bonnadous, M., Cros, S., and Meunier, B. (1987) The Biooxidation of Cytotoxic Ellipticine Derivatives: A Key to Structure-Activity Relationship Studies? Mol. Pharmacol. 33, 93-102.
    • (1987) Mol. Pharmacol. , vol.33 , pp. 93-102
    • Meunier, G.1    De Montauzon, D.2    Bernadou, J.3    Grassy, G.4    Bonnadous, M.5    Cros, S.6    Meunier, B.7
  • 92
    • 0018641928 scopus 로고
    • Catecholamine Analogs as Potential Antitumor Agents
    • Driacoll, J. S. (1979) Catecholamine Analogs as Potential Antitumor Agents. J. Pharm. Sci. 68, 1519-1521.
    • (1979) J. Pharm. Sci. , vol.68 , pp. 1519-1521
    • Driacoll, J.S.1
  • 93
    • 0025169721 scopus 로고
    • Preparation, Reactivity, and Neurotoxicity of Tryptamine-4,5-Dione
    • Cai, P., Snyder, J. K., Chen, J.-C., Fine, R., and Volicer, L. (1990) Preparation, Reactivity, and Neurotoxicity of Tryptamine-4,5-Dione. Tetrahedron Lett, 31, 969-972.
    • (1990) Tetrahedron Lett , vol.31 , pp. 969-972
    • Cai, P.1    Snyder, J.K.2    Chen, J.-C.3    Fine, R.4    Volicer, L.5
  • 94
    • 0019350351 scopus 로고
    • Regiospecific attack of nitrogen and sulfur nucleophiles on quinones derived from poison oak/ivy catechols (urushiols) and analogues as models for urushiol-protein conjugate formation
    • Liberate, D. J., Byers, V. S., Dennick, R. G., and Castagnoli, N. (1981) Regiospecific attack of nitrogen and sulfur nucleophiles on quinones derived from poison oak/ivy catechols (urushiols) and analogues as models for urushiol-protein conjugate formation. J. Med. Chem. 24, 28-33.
    • (1981) J. Med. Chem. , vol.24 , pp. 28-33
    • Liberate, D.J.1    Byers, V.S.2    Dennick, R.G.3    Castagnoli, N.4
  • 95
    • 0017066816 scopus 로고
    • Cytochrome P450-mediated oxidation of 2-hydroxyestrogens to reactive intermediates
    • Nelson, S. D., Mitchell, J. R., Dybing, E., and Sasame, H. A. (1976) Cytochrome P450-mediated oxidation of 2-hydroxyestrogens to reactive intermediates. Biochem. Biophys. Res. Commun. 70, 1157-1165.
    • (1976) Biochem. Biophys. Res. Commun. , vol.70 , pp. 1157-1165
    • Nelson, S.D.1    Mitchell, J.R.2    Dybing, E.3    Sasame, H.A.4
  • 96
    • 0024675018 scopus 로고
    • Covalent binding to proteins of reactive intermediates resulting from prostaglandin H synthase-catalyzed oxidation of stilbene and steroid estrogens
    • Freyberger, A., and Degen, G. H. (1989) Covalent binding to proteins of reactive intermediates resulting from prostaglandin H synthase-catalyzed oxidation of stilbene and steroid estrogens. J. Biochem. Toxicol. 4, 95-103.
    • (1989) J. Biochem. Toxicol. , vol.4 , pp. 95-103
    • Freyberger, A.1    Degen, G.H.2
  • 97
    • 0028037863 scopus 로고
    • Reaction of lysine with estrone 3,4-o-quinone
    • Tabakovic, K., and Abul-Hajj, Y. (1994) Reaction of lysine with estrone 3,4-o-quinone. Chem. Res. Toxicol. 7, 696-701.
    • (1994) Chem. Res. Toxicol. , vol.7 , pp. 696-701
    • Tabakovic, K.1    Abul-Hajj, Y.2
  • 99
    • 0028010806 scopus 로고
    • Identification of fatty acid hydro peroxide cofactors in the cytochrome P450-mediated oxidation of estrogens to quinone metabolites. Role and balance of lipid peroxides during estrogen-induced carcinogenesis
    • Wang, M., and Liehr, J. G. (1994) Identification of fatty acid hydro peroxide cofactors in the cytochrome P450-mediated oxidation of estrogens to quinone metabolites. Role and balance of lipid peroxides during estrogen-induced carcinogenesis. J. Biol. Chem. 269, 284-291.
    • (1994) J. Biol. Chem. , vol.269 , pp. 284-291
    • Wang, M.1    Liehr, J.G.2
  • 100
    • 0029086898 scopus 로고
    • Induction by estrogens of lipid peroxidation and lipid peroxide-derived malonaldehydeDNA adducts in male Syrian hamsters: Role of lipid peroxidation in estrogen-induced kidney carcinogenesis
    • Wang, M. Y., and Liehr, J. G. (1995) Induction by estrogens of lipid peroxidation and lipid peroxide-derived malonaldehydeDNA adducts in male Syrian hamsters: role of lipid peroxidation in estrogen-induced kidney carcinogenesis. Carcinogenesis 16, 1941-1945.
    • (1995) Carcinogenesis , vol.16 , pp. 1941-1945
    • Wang, M.Y.1    Liehr, J.G.2
  • 101
    • 0025973702 scopus 로고
    • Assays for 8-hydroxy2'-deoxyguanosine: A biomarker of in vivo oxidative DNA damage
    • Shigenaga, M. K., and Ames, B. N. (1991) Assays for 8-hydroxy2'-deoxyguanosine: A biomarker of in vivo oxidative DNA damage. Free Radical Biol. Med. 10, 211-216.
    • (1991) Free Radical Biol. Med. , vol.10 , pp. 211-216
    • Shigenaga, M.K.1    Ames, B.N.2
  • 102
    • 0023547926 scopus 로고
    • Metabolism and Reactions of Quinoid Anticancer Agents
    • Powis, G. (1987) Metabolism and Reactions of Quinoid Anticancer Agents. Pharmacol. Ther. 35, 57-162.
    • (1987) Pharmacol. Ther. , vol.35 , pp. 57-162
    • Powis, G.1
  • 103
  • 104
    • 0000707654 scopus 로고
    • Chemical modification of biopolymers with quinones and quinone methides
    • Peter, M. G. (1989) Chemical modification of biopolymers with quinones and quinone methides. Angew. Chem. 101, 572-587.
    • (1989) Angew. Chem. , vol.101 , pp. 572-587
    • Peter, M.G.1
  • 105
    • 0029850686 scopus 로고    scopus 로고
    • Alkylation of 2'-Deoxynucleosides and DNA by Quinone Methides Derived from 2,6-Di-tert-butyl-4-methylphenol
    • 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.
    • (1996) Chem. Res. Toxicol. , vol.9 , pp. 1368-1374
    • Lewis, M.A.1    Yoerg-Graff, D.2    Bolton, J.L.3    Thompson, J.A.4
  • 106
    • 0031434490 scopus 로고    scopus 로고
    • Influence of quinone methide reactivity on the alkylation of thiol and amino groups in proteins: Studies utilizing amino acid and peptide models
    • Bolton, J. L., Turnipseed, S. B., and Thompson, J. A. (1997) Influence of quinone methide reactivity on the alkylation of thiol and amino groups in proteins: studies utilizing amino acid and peptide models, Chem.-Biol. Interact. 107, 185-200.
    • (1997) Chem.-Biol. Interact. , vol.107 , pp. 185-200
    • Bolton, J.L.1    Turnipseed, S.B.2    Thompson, J.A.3
  • 107
    • 0001466726 scopus 로고
    • The effect of β-fluorine substituents on the rate and equilibrium constants for the reactions of α-substituted 4-methoxybenzyl carbocations and on the reactivity of a simple quinone methide
    • Richard, J. P., Amyes, T. L., Bei, L., and Stubblefield, V. (1990) The effect of β-fluorine substituents on the rate and equilibrium constants for the reactions of α-substituted 4-methoxybenzyl carbocations and on the reactivity of a simple quinone methide. J. Am. Chem. Soc. 112, 9513-9519.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 9513-9519
    • Richard, J.P.1    Amyes, T.L.2    Bei, L.3    Stubblefield, V.4
  • 108
    • 0021021388 scopus 로고
    • Chemical rearrangement of phenol-epoxide metabolites of polycyclic aromatic hydrocarbons to quinone-methides
    • Hulbert, P. B., and Grover, P. L. (1983) Chemical rearrangement of phenol-epoxide metabolites of polycyclic aromatic hydrocarbons to quinone-methides. Biochem. Biophys. Res. Commun. 117, 129-134.
    • (1983) Biochem. Biophys. Res. Commun. , vol.117 , pp. 129-134
    • Hulbert, P.B.1    Grover, P.L.2
  • 109
    • 0024465355 scopus 로고
    • Redox and Addition Chemistry of Quinoid Compounds and its Biological Implications
    • Brunmark, A., and Cadenas, E. (1989) Redox and Addition Chemistry of Quinoid Compounds and its Biological Implications. Free Radical Biol. Med. 7, 435-477.
    • (1989) Free Radical Biol. Med. , vol.7 , pp. 435-477
    • Brunmark, A.1    Cadenas, E.2
  • 110
    • 0029969531 scopus 로고    scopus 로고
    • Role of NAD(P)H:quinone oxidoreductase (DT-diaphorase) in cytotoxicity and induction of DNA damage by streptonigrin
    • Beall, H. D., Liu, Y., Siegel, D., Bolton, E. M., Gibson, N. W., and Ross, D. (1996) Role of NAD(P)H:quinone oxidoreductase (DT-diaphorase) in cytotoxicity and induction of DNA damage by streptonigrin. Biochem. Pharmacol. 51, 645-652.
    • (1996) Biochem. Pharmacol. , vol.51 , pp. 645-652
    • Beall, H.D.1    Liu, Y.2    Siegel, D.3    Bolton, E.M.4    Gibson, N.W.5    Ross, D.6
  • 111
    • 0025248106 scopus 로고
    • Cytosolic NAD(P)H:quinone acceptor oxidoreductase in human normal and tumor tissue. Effects of cigarette smoking and alcohol
    • Schlager, J. J., and Powis, G. (1990) Cytosolic NAD(P)H:quinone acceptor oxidoreductase in human normal and tumor tissue. Effects of cigarette smoking and alcohol. Int. J. Cancer 45, 403-409.
    • (1990) Int. J. Cancer , vol.45 , pp. 403-409
    • Schlager, J.J.1    Powis, G.2
  • 113
    • 0028144399 scopus 로고
    • An o-quinone form of estrogen produces free radicals in human breast cancer cells: Correlation with DNA damage
    • Nutter, L. M., Wu, Y., Ngo, E. O., Sierra, E. E., Gutierrez, P. L., and Abul-Hajj, Y. J. (1994) An o-quinone form of estrogen produces free radicals in human breast cancer cells: Correlation with DNA damage. Chem. Res. Toxicol. 7, 23-28.
    • (1994) Chem. Res. Toxicol. , vol.7 , pp. 23-28
    • Nutter, L.M.1    Wu, Y.2    Ngo, E.O.3    Sierra, E.E.4    Gutierrez, P.L.5    Abul-Hajj, Y.J.6
  • 114
    • 0023840830 scopus 로고
    • Temporary decrease in renal quinone reductase activity induced by chronic administration of estradiol to male Syrian hamsters: Increased Superoxide formation by redox cycling of estrogen
    • Roy, D., and Liehr, J. G. (1988) Temporary decrease in renal quinone reductase activity induced by chronic administration of estradiol to male Syrian hamsters: Increased Superoxide formation by redox cycling of estrogen. J. Biol. Chem. 263, 3646-3651.
    • (1988) J. Biol. Chem. , vol.263 , pp. 3646-3651
    • Roy, D.1    Liehr, J.G.2
  • 115
    • 0002265018 scopus 로고
    • Protocols for screening chemical agents and natural products against animal tumors and other biological systems (third edition)
    • Geran, R. I., Greenberg, N. H., McDonald, M. M., Schumacher, A. M., and Abbott, B. J. (1972) Protocols for screening chemical agents and natural products against animal tumors and other biological systems (third edition). Cancer Chemother. Rep. 3, 1-103.
    • (1972) Cancer Chemother. Rep. , vol.3 , pp. 1-103
    • Geran, R.I.1    Greenberg, N.H.2    McDonald, M.M.3    Schumacher, A.M.4    Abbott, B.J.5
  • 116
    • 0027404651 scopus 로고
    • Cytotoxic and antimalarial bisbenzylisoquinoline alkaloids from Stephania Erecta
    • Likhitwitayawuid, K., Angerhofer, C. K., Cordeil, G. A., and Pezzuto, J. M. (1993) Cytotoxic and antimalarial bisbenzylisoquinoline alkaloids from Stephania Erecta, J. Nat. Prod. 56, 3038.
    • (1993) J. Nat. Prod. , vol.56 , pp. 3038
    • Likhitwitayawuid, K.1    Angerhofer, C.K.2    Cordeil, G.A.3    Pezzuto, J.M.4
  • 117
    • 0030890101 scopus 로고    scopus 로고
    • Cell-based assay for the determination of estrogenic and anti-estrogenic activities
    • 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.
    • (1997) Methods Cell Sci , vol.19 , pp. 37-43
    • Pisha, E.1    Pezzuto, J.M.2
  • 118
    • 0030693983 scopus 로고    scopus 로고
    • The reactivity of o-quinones which do not isomerize to quinone methides correlates with alkycatechol-induced toxicity in human melanoma cells
    • Bolton, J. L., Pisha, E., Shen, L., Krol, E. S., Iverson, S. L., Huang, Z., van Breemen, R. B., and Pezzuto, J. M. (1997) The reactivity of o-quinones which do not isomerize to quinone methides correlates with alkycatechol-induced toxicity in human melanoma cells. Chem.-Biol. Interact. 106, 133-148.
    • (1997) Chem.-Biol. Interact. , vol.106 , pp. 133-148
    • Bolton, J.L.1    Pisha, E.2    Shen, L.3    Krol, E.S.4    Iverson, S.L.5    Huang, Z.6    Van Breemen, R.B.7    Pezzuto, J.M.8
  • 119
    • 0030002986 scopus 로고    scopus 로고
    • Progession of human breast cancers to the metastatic state is linked to hydroxyl radical-induced DNA damage
    • Malins, D. C., Polissar, N. L., and Gunselman, S. J. (1996) Progession of human breast cancers to the metastatic state is linked to hydroxyl radical-induced DNA damage. Proc. Natl. Acad. Sci. U.S.A. 93, 2557-2563.
    • (1996) Proc. Natl. Acad. Sci. U.S.A. , vol.93 , pp. 2557-2563
    • Malins, D.C.1    Polissar, N.L.2    Gunselman, S.J.3
  • 120
    • 0025973702 scopus 로고
    • Assays for 8-hydroxy2'-deoxyguanosine: A biomarker of in vivo oxidative DNA damage
    • Shigenaga, M. K., and Ames, B. N. (1991) Assays for 8-hydroxy2'-deoxyguanosine: A biomarker of in vivo oxidative DNA damage. Free Radical Biol. Med. 10, 211-216.
    • (1991) Free Radical Biol. Med. , vol.10 , pp. 211-216
    • Shigenaga, M.K.1    Ames, B.N.2
  • 121
    • 0025045198 scopus 로고
    • The role of 8-hydroxyguanine in carcinogenesis
    • Floyd, R. A. (1990) The role of 8-hydroxyguanine in carcinogenesis. Carcinogenesis 11, 1447-1450.
    • (1990) Carcinogenesis , vol.11 , pp. 1447-1450
    • Floyd, R.A.1
  • 123
    • 0027960577 scopus 로고
    • 8-Hydroxylation of guanine bases in kidney and liver DNA of hamsters treated with estradiol. Role of free radicals in estrogen-induced carcinogenesis
    • Han, X., and Liehr, J. G. (1994) 8-Hydroxylation of guanine bases in kidney and liver DNA of hamsters treated with estradiol. Role of free radicals in estrogen-induced carcinogenesis. Cancer Res. 54, 5515-5517.
    • (1994) Cancer Res , vol.54 , pp. 5515-5517
    • Han, X.1    Liehr, J.G.2
  • 124
    • 0026063210 scopus 로고
    • Characterization of DNA damage induced by 3,4-estrone-o-quinone in human cells
    • 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.
    • (1991) J. Biol. Chem. , vol.266 , pp. 16380-16386
    • Nutter, L.M.1    Ngo, E.O.2    Abul-Hajj, Y.J.3
  • 125
    • 0027960577 scopus 로고
    • 8-Hydroxylation of guanine bases in kidney and liver DNA of hamsters treated with estradiol. Role of free radicals in estrogen-induced carcinogenesis
    • Han, X., and Liehr, J. G. (1994) 8-Hydroxylation of guanine bases in kidney and liver DNA of hamsters treated with estradiol. Role of free radicals in estrogen-induced carcinogenesis. Cancer Res. 54, 5515-5517.
    • (1994) Cancer Res , vol.54 , pp. 5515-5517
    • Han, X.1    Liehr, J.G.2
  • 126
    • 0027818392 scopus 로고
    • Estrogen carcinogenesis in the hamster kidney: Role of cytotoxicity and cell proliferation
    • Li, J. J., Gonzalez, A., Banerjee, S., Banerjee, S. K., and Li, S. A. (1993) Estrogen carcinogenesis in the hamster kidney: role of cytotoxicity and cell proliferation. Environ. Health Perspect. 5, 259-264.
    • (1993) Environ. Health Perspect. , vol.5 , pp. 259-264
    • Li, J.J.1    Gonzalez, A.2    Banerjee, S.3    Banerjee, S.K.4    Li, S.A.5
  • 127
    • 0028104962 scopus 로고
    • Induction of chromosome aberrations in Syrian hamster renal cortical cells by various estrogens
    • Banerjee, S. K., Banerjee, S., Li, S. A., and Li, J. J. (1994) Induction of chromosome aberrations in Syrian hamster renal cortical cells by various estrogens. Mutat. Res. 311, 191-197.
    • (1994) Mutat. Res. , vol.311 , pp. 191-197
    • Banerjee, S.K.1    Banerjee, S.2    Li, S.A.3    Li, J.J.4
  • 128
    • 0025236462 scopus 로고
    • Inhibition of estrogen-induced kidney carcinogenesis in Syrian hamsters by modulators of estrogen metabolism
    • Roy, D., and Liehr, J. C. (1990) Inhibition of estrogen-induced kidney carcinogenesis in Syrian hamsters by modulators of estrogen metabolism. Carcinogenesis 11, 567-570.
    • (1990) Carcinogenesis , vol.11 , pp. 567-570
    • Roy, D.1    Liehr, J.C.2
  • 129
    • 0025840462 scopus 로고
    • Vitamin C reduces the incidence and severity of renal tumors induced by estradiol or diethylstilbestrol
    • Liehr, J. G. (1991) Vitamin C reduces the incidence and severity of renal tumors induced by estradiol or diethylstilbestrol. Am. J. Clin. Nutr. 54, 1256S-1260S.
    • (1991) Am. J. Clin. Nutr. , vol.54
    • Liehr, J.G.1
  • 130
    • 0025938226 scopus 로고
    • Major alterations in the nucleotide structure of DNA in cancer of the female breast
    • Malins, D. C., and Haimanot, R. (1991) Major alterations in the nucleotide structure of DNA in cancer of the female breast. Cancer Res. 51, 5430-5432.
    • (1991) Cancer Res , vol.51 , pp. 5430-5432
    • Malins, D.C.1    Haimanot, R.2
  • 132
    • 0031692626 scopus 로고    scopus 로고
    • The equine estrogen metabolite 4-hydroxyequilenin causes DNA single strand breaks and oxidation of DNA bases in vitro
    • in press
    • 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 (in press).
    • (1998) Chem. Res. Toxicol
    • Chen, Y.1    Shen, L.2    Zhang, F.3    Lau, S.S.4    Van Breemen, R.B.5    Nikolic, D.6    Bolton, J.L.7
  • 133
    • 0028785835 scopus 로고
    • Microsome-mediated 8-hydroxylation of guanine bases of DNA by steroid estrogens: Correlation of DNA damage by free radicals with metabolic activation to quinones
    • 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.
    • (1995) Carcinogenesis , vol.16 , pp. 2571-2574
    • Han, X.1    Liehr, J.G.2
  • 135
    • 0023647116 scopus 로고
    • Misreading of DNA templates containing 8-hydroxydeoxyguanosine at the modified base and at adjacent residues
    • Kuchino, Y., Mari, F., Kasai, H., Inoue, H., Iwai, S., Miura, K., Ohtsuka, E., and Nishimura, S. (1987) Misreading of DNA templates containing 8-hydroxydeoxyguanosine at the modified base and at adjacent residues. Nature 327, 77-79.
    • (1987) Nature , vol.327 , pp. 77-79
    • Kuchino, Y.1    Mari, F.2    Kasai, H.3    Inoue, H.4    Iwai, S.5    Miura, K.6    Ohtsuka, E.7    Nishimura, S.8
  • 137
    • 0030787013 scopus 로고    scopus 로고
    • What structual features determine repair enzyme specificity and mechanism in chemically modified DNA?
    • 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.
    • (1997) Chem. Res. Toxicol. , vol.10 , pp. 713-732
    • Singer, B.1    Hang, B.2
  • 138
    • 0004949368 scopus 로고
    • Estrogen-induced endogenous DNA adduction; Possible mechanism of hormonal cancer
    • Liehr, J. G., Avitts, T. A., Randerath, B., and Randerath, K. (1986) Estrogen-induced endogenous DNA adduction; Possible mechanism of hormonal cancer, Proc. Natl. Acad. Sci U.S.A. 83, 5301-5305.
    • (1986) Proc. Natl. Acad. Sci U.S.A. , vol.83 , pp. 5301-5305
    • Liehr, J.G.1    Avitts, T.A.2    Randerath, B.3    Randerath, K.4
  • 139
    • 0023202816 scopus 로고
    • Localization of estrogen-induced DNA adducts and cytochrome P450 activity at the site of renal carcinogenesis in the hamster kidney
    • 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.
    • (1987) Cancer Res , vol.47 , pp. 2156-2159
    • Liehr, J.G.1    Hall, E.R.2    Avitts, T.A.3    Randerath, E.4    Randerath, K.5
  • 140
    • 0028960390 scopus 로고
    • 32P-postlabeling in the dorsolateral prostrate of NBL/Cr rats treated with estradiol-17β and testosterone
    • 32P-postlabeling in the dorsolateral prostrate of NBL/Cr rats treated with estradiol-17β and testosterone. Carcinogenesis 16, 951-954.
    • (1995) Carcinogenesis , vol.16 , pp. 951-954
    • Han, X.1    Liehr, J.G.2    Bosland, M.C.3
  • 141
    • 0027097569 scopus 로고
    • 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
    • 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.
    • (1992) Chem. Res. Toxicol. , vol.5 , pp. 828-833
    • Dwivedy, I.1    Devanesan, P.2    Cremonesi, P.3    Rogan, E.4    Cavalieri, E.5
  • 142
    • 0031408145 scopus 로고    scopus 로고
    • Estrogen-nucleic acid adducts; guanine is major site for interaction between 3,4-estrone quinone and COIII gene
    • Roy, D., and Abul-Hajj, Y. J. (1997) Estrogen-nucleic acid adducts; guanine is major site for interaction between 3,4-estrone quinone and COIII gene. Carcinogenesis 18, 1247-1249.
    • (1997) Carcinogenesis , vol.18 , pp. 1247-1249
    • Roy, D.1    Abul-Hajj, Y.J.2
  • 143
    • 0029005370 scopus 로고
    • An estrogen-nucleic acid adduct. Electroreductive intermolecular coupling of 3,4-estrone-o-quinone and adenine
    • 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.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 6144-6145
    • Abul-Hajj, Y.J.1    Tabakovic, K.2    Tabakovic, I.3
  • 144
    • 0030911971 scopus 로고    scopus 로고
    • Estrogennucleic acid adducts; Reaction of 3,4-estrone-o-quinone with nucleic acid bases
    • 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.
    • (1997) Chem. Res. Toxicol. , vol.10 , pp. 477-481
    • Akanni, A.1    Tabakovic, K.2    Abul-Hajj, Y.J.3
  • 145
    • 0030797641 scopus 로고    scopus 로고
    • Estrogen-nucleic acid adducts; Reaction of 3,4-estrone-o-quinone radical anion with deoxynucleosides
    • 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.
    • (1997) Chem. Res. Toxicol. , vol.10 , pp. 760-766
    • Akanni, A.1    Abul-Hajj, Y.J.2
  • 146
    • 0029680465 scopus 로고    scopus 로고
    • Molecular characteristics of catechol estrogen quinones in reactions with deoxyribonucleosides
    • 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.
    • (1996) Chem. Res. Toxicol. , vol.9 , pp. 851-859
    • Stack, D.E.1    Byun, J.2    Gross, M.L.3    Rogan, E.G.4    Cavalieri, E.L.5
  • 147
    • 0023015325 scopus 로고
    • Mutagenesis by apurinic/ apyrimidinic sites
    • Loeb, L. A., and Preston, B. D. (1986) Mutagenesis by apurinic/ apyrimidinic sites. Annu. Rev. Genet. 20, 201-203.
    • (1986) Annu. Rev. Genet. , vol.20 , pp. 201-203
    • Loeb, L.A.1    Preston, B.D.2
  • 149
    • 0030688956 scopus 로고    scopus 로고
    • Reaction of the Premarin metabolite 4-hydroxyequilenin semiquinone radical with 2'-deoxyguanosine: Formation of unusual cyclic adducts
    • 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.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 11126-11127
    • Shen, L.1    Qiu, S.2    Van Breemen, R.B.3    Zhang, F.4    Chen, Y.5    Bolton, J.L.6
  • 150
    • 0031931940 scopus 로고    scopus 로고
    • Alkylation of 2'-deoxynucleosides and DNA by the Premarin metabolite 4-hydroxyequilenin semiquinone radical
    • Shen, L., Qiu, S., Chen, Y., Zhang, F., van Breemen, R. B., Nikolic, D., and Bolton, J. L. (1998) Alkylation of 2'-deoxynucleosides and DNA by the Premarin metabolite 4-hydroxyequilenin semiquinone radical. Chem. Res. Toxicol. 11, 94-101.
    • (1998) Chem. Res. Toxicol. , vol.11 , pp. 94-101
    • Shen, L.1    Qiu, S.2    Chen, Y.3    Zhang, F.4    Van Breemen, B.R.5    Nikolic, D.6    Bolton, J.L.7


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