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Volumn 9, Issue 5, 1996, Pages 860-865

Oxidative transformation of 2-hydroxyestrone. Stability and reactivity of 2,3-estrone quinone and its relationship to estrogen carcinogenicity

Author keywords

[No Author keywords available]

Indexed keywords

2 HYDROXYESTRONE; CATECHOL ESTROGEN; ESTRADIOL; ESTROGEN; ESTRONE DERIVATIVE; QUINONE DERIVATIVE;

EID: 0029680467     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx950205z     Document Type: Article
Times cited : (27)

References (38)
  • 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
  • 6
    • 78651128652 scopus 로고
    • Estrogen-induced tumors of the kidney in the Syrian hamster. III. Growth characteristics in the Syrian hamster
    • Kirkman, H. (1984) Estrogen-induced tumors of the kidney in the Syrian hamster. III. Growth characteristics in the Syrian hamster. Natl. Cancer Inst. Monogr. 1, 1-57.
    • (1984) Natl. Cancer Inst. Monogr. , vol.1 , pp. 1-57
    • Kirkman, H.1
  • 7
    • 0025373464 scopus 로고
    • Genotoxic effects of estrogens
    • Liehr, J. G. (1990) Genotoxic effects of estrogens. Mutat. Res. 228, 269-276.
    • (1990) Mutat. Res. , vol.228 , pp. 269-276
    • Liehr, J.G.1
  • 8
    • 0022272166 scopus 로고
    • Semiquinone radicals of catecholamines, catecholestrogens, and their metal ion complexes
    • Kalyanaraman, B., Felix, C. C., and Sealy, R. C. (1985) Semiquinone radicals of catecholamines, catecholestrogens, and their metal ion complexes. Environ. Health Perspect. 64, 185-198.
    • (1985) Environ. Health Perspect. , vol.64 , pp. 185-198
    • Kalyanaraman, B.1    Felix, C.C.2    Sealy, R.C.3
  • 9
    • 0025152273 scopus 로고
    • Role of prostaglandin-H synthase in mediating genotoxic and carcinogenic effects of estrogens
    • Degen, G. H. (1990) Role of prostaglandin-H synthase in mediating genotoxic and carcinogenic effects of estrogens. Environ. Health Perspect. 88, 217-223.
    • (1990) Environ. Health Perspect. , vol.88 , pp. 217-223
    • Degen, G.H.1
  • 10
    • 0021320115 scopus 로고
    • The mechanistic plurality of cytochrome P-450 and its biological ramifications
    • Capdevila, J., Sack, Y., and Falck, J. R. (1984) The mechanistic plurality of cytochrome P-450 and its biological ramifications. Xenobiotica 14, 105-118.
    • (1984) Xenobiotica , vol.14 , pp. 105-118
    • Capdevila, J.1    Sack, Y.2    Falck, J.R.3
  • 11
    • 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.-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.-Y.2    Ngo, E.O.3    Sierra, E.E.4    Gutierrez, P.L.5    Abul-Hajj, Y.J.6
  • 12
    • 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. 226, 16380-16386.
    • (1991) J. Biol. Chem. , vol.226 , pp. 16380-16386
    • Nutter, L.M.1    Ngo, E.O.2    Abul-Hajj, Y.J.3
  • 14
    • 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
  • 15
    • 0024207251 scopus 로고
    • 4-Hydroxyestradiol is conjugated with thiols primarily at C-2: Evidence from regio-specific displacement of tritium by cat liver microsomes or tyrosinase
    • Jellinck, P. H. (1988) 4-Hydroxyestradiol is conjugated with thiols primarily at C-2: Evidence from regio-specific displacement of tritium by cat liver microsomes or tyrosinase. Steroids 51, 395-409.
    • (1988) Steroids , vol.51 , pp. 395-409
    • Jellinck, P.H.1
  • 16
    • 0021117986 scopus 로고
    • Nutritional consequences of the reactions between proteins and oxidized polyphenolic acids
    • Hurrell, R. F., and Finot, P. A. (1984) Nutritional consequences of the reactions between proteins and oxidized polyphenolic acids. Adv. Exp. Med. Biol. 177, 423-434.
    • (1984) Adv. Exp. Med. Biol. , vol.177 , pp. 423-434
    • Hurrell, R.F.1    Finot, P.A.2
  • 17
    • 0020024569 scopus 로고
    • Protein-polyphenol reactions. I. Nutritional and metabolic consequences of the reactions between oxidized caffeic acid and the lysine residues of casein
    • Hurrell, R. F., Finot, P. A., and Cuq, J. L. (1982) Protein-polyphenol reactions. I. Nutritional and metabolic consequences of the reactions between oxidized caffeic acid and the lysine residues of casein. Br. J. Nutr. 47, 191-211.
    • (1982) Br. J. Nutr. , vol.47 , pp. 191-211
    • Hurrell, R.F.1    Finot, P.A.2    Cuq, J.L.3
  • 18
    • 0028037863 scopus 로고
    • Reaction of L-lysine with estrone-3,4-o-quinone
    • Tabakovic, K., and Abul-Hajj, Y. J. (1994) Reaction of L-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.J.2
  • 19
    • 0029949186 scopus 로고    scopus 로고
    • Reactions of 3,4-estrone quinone with mimics of amino acid side chains
    • Abul-Hajj, Y. J., Tabakovic, K., Gleason, W. B., and Ojala, W. H. (1996) Reactions of 3,4-estrone quinone with mimics of amino acid side chains. Chem. Res. Toxicol. 9, 434-438.
    • (1996) Chem. Res. Toxicol. , vol.9 , pp. 434-438
    • Abul-Hajj, Y.J.1    Tabakovic, K.2    Gleason, W.B.3    Ojala, W.H.4
  • 20
    • 0020471249 scopus 로고
    • Relative rates of 2- And 4-hydroxyestrogen synthesis are dependent on both substrate and tissue
    • Purdy, R. H., Moore, P. H., Jr., Williams, M. C., Goldzieher, J. 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 Jr., P.H.2    Williams, M.C.3    Goldzieher, J.W.4    Paul, S.M.5
  • 21
    • 0026510286 scopus 로고
    • 3H] 17β-oestradiol in rats: Male-specific 15α- And male-selective 16α-hydroxylation and female-selective catechol formation
    • 3H] 17β-oestradiol in rats: Male-specific 15α- and male-selective 16α-hydroxylation and female-selective catechol formation. J. Steroid Biochem. 42, 65-76.
    • (1992) J. Steroid Biochem. , vol.42 , pp. 65-76
    • Maggs, J.L.1    Morgan, P.2    Park, B.K.3
  • 22
    • 0000161063 scopus 로고
    • Role of 2-hydroxyestrone in estrogen metabolism
    • Fishman, J. (1963) Role of 2-hydroxyestrone in estrogen metabolism. J. Clin. Endocrinol. Metab. 23, 207-210.
    • (1963) J. Clin. Endocrinol. Metab. , vol.23 , pp. 207-210
    • Fishman, J.1
  • 23
    • 0017093511 scopus 로고
    • Convenient large scale preparation of catechol estrogens
    • Stubenrauch, G., and Knuppen, R. (1976) Convenient large scale preparation of catechol estrogens. Steroids 28, 733-741.
    • (1976) Steroids , vol.28 , pp. 733-741
    • Stubenrauch, G.1    Knuppen, R.2
  • 24
    • 0021721967 scopus 로고
    • Synthesis of 3,4-estrogen-o-quinones
    • Abul-Hajj, Y. J. (1984) Synthesis of 3,4-estrogen-o-quinones. J. Steroid Biochem. 21, 621-622.
    • (1984) J. Steroid Biochem. , vol.21 , pp. 621-622
    • Abul-Hajj, Y.J.1
  • 25
    • 85033043146 scopus 로고
    • NIH Publication No. 81-2385, U.S. Government Printing Office, Washington, DC
    • NIH Guidelines for the Laboratory Use of Chemical Carcinogens (1981) NIH Publication No. 81-2385, U.S. Government Printing Office, Washington, DC.
    • (1981)
  • 28
    • 0003528616 scopus 로고
    • Molecular Structure Corporation, The Woodlands, Texas.
    • TEXSAN-TEXRAY (1985) Structure Analysis Package, Molecular Structure Corporation, The Woodlands, Texas.
    • (1985) Structure Analysis Package
  • 30
    • 0025099288 scopus 로고
    • The O-methylation of 4-hydroxyestradiol is inhibited by 2-hydroxyestradiol: Implications for estrogen-induced carcinogenesis
    • Roy, D., Weisz, J., and Liehr, J. G. (1990) The O-methylation of 4-hydroxyestradiol is inhibited by 2-hydroxyestradiol: implications for estrogen-induced carcinogenesis. Carcinogenesis 11, 459-462.
    • (1990) Carcinogenesis , vol.11 , pp. 459-462
    • Roy, D.1    Weisz, J.2    Liehr, J.G.3
  • 31
    • 0028123447 scopus 로고
    • Estrogen quinones: Reaction with propylamine
    • Khasnis, D., and Abul-Hajj, Y. J. (1994) Estrogen quinones: Reaction with propylamine. Chem. Res. Toxicol. 7, 68-72.
    • (1994) Chem. Res. Toxicol. , vol.7 , pp. 68-72
    • Khasnis, D.1    Abul-Hajj, Y.J.2
  • 32
    • 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
  • 33
    • 0017763972 scopus 로고
    • Two dimers, 4:4′- And 2:2′-di(estradiol), obtained by chemical oxidative coupling of estradiol
    • Ins, A., Meroni, G., and Ferrara, L. (1977) Two dimers, 4:4′- and 2:2′-di(estradiol), obtained by chemical oxidative coupling of estradiol. J. Steroid Biochem. 8, 1259-1261.
    • (1977) J. Steroid Biochem. , vol.8 , pp. 1259-1261
    • Ins, A.1    Meroni, G.2    Ferrara, L.3
  • 34
    • 0001217545 scopus 로고
    • Quinones as oxidants and dehydrogenation agents
    • (Patai, S., and Rappaport, Z., Eds.) Wiley
    • Becker, H. D., and Turner, A. B. (1988) Quinones as oxidants and dehydrogenation agents. In The Chemistry of Quinonoid Compounds (Patai, S., and Rappaport, Z., Eds.) Wiley.
    • (1988) The Chemistry of Quinonoid Compounds
    • Becker, H.D.1    Turner, A.B.2
  • 35
    • 0029061720 scopus 로고
    • The influence of the p-alkyl substituents on the isomerization of o-quinones top-quinone methides: Potential bioactivation mechanism for catechols
    • Iverson, S. L., Hu, L. Q., Vukomanovic, V., and Bolton, J. L. (1995) The influence of the p-alkyl substituents on the isomerization of o-quinones top-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
  • 36
    • 0018853550 scopus 로고
    • Catechol estrogens: Chemistry, biogenesis, metabolism, occurrence and physiological significance
    • Ball, P., and Knuppen, R. (1980) Catechol estrogens: Chemistry, biogenesis, metabolism, occurrence and physiological significance. Acta Endocr., Copenh. 132, 1-127.
    • (1980) Acta Endocr., Copenh. , vol.132 , pp. 1-127
    • Ball, P.1    Knuppen, R.2
  • 37
    • 85033051705 scopus 로고    scopus 로고
    • (personal communication)
    • Bolton, J. L. (personal communication).
    • Bolton, J.L.1
  • 38
    • 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


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