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Volumn 9, Issue 2, 1996, Pages 492-499

Bioactivation of estrone and its catechol metabolites to quinoid-glutathione conjugates in rat liver microsomes

Author keywords

[No Author keywords available]

Indexed keywords

1,4 BENZOQUINONE; 2 HYDROXYESTRONE; CATECHOL ESTROGEN; CYTOCHROME P450; DRUG METABOLITE; ESTRONE; ESTRONE DERIVATIVE; QUINONE DERIVATIVE; TETRALIN DERIVATIVE;

EID: 0029924611     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx950178c     Document Type: Article
Times cited : (93)

References (47)
  • 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
  • 2
    • 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
  • 3
    • 0019311649 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. Logica 93, 1-127.
    • (1980) Acta Endocrinol. Logica , vol.93 , pp. 1-127
    • Ball, P.1    Knuppen, R.2
  • 4
    • 0027167145 scopus 로고
    • P450 enzymes of estrogen metabolism
    • Martucci, C. P., and Fishman, J. (1993) P450 enzymes of estrogen metabolism. Pharmacol Ther. 57, 237-254.
    • (1993) Pharmacol Ther. , vol.57 , pp. 237-254
    • Martucci, C.P.1    Fishman, J.2
  • 5
    • 0025313058 scopus 로고
    • Free radical generation by redox cycling of estrogens
    • Liehr, J. G., and Roy, D. (1990) Free radical generation by redox cycling of estrogens. Free Radical Biol. Med. 8, 415-423.
    • (1990) Free Radical Biol. Med. , vol.8 , pp. 415-423
    • Liehr, J.G.1    Roy, D.2
  • 6
    • 0028237181 scopus 로고
    • DNA damage caused by reactive oxygen species originating from a copper-dependent oxidation of the 2-hydroxy catechol of estradiol
    • 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.
    • (1994) Carcinogenesis , vol.15 , pp. 1421-1427
    • Li, Y.1    Trush, M.A.2    Yager, J.D.3
  • 7
    • 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
  • 8
    • 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 Cavaheri, 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    Cavaheri, E.5
  • 9
    • 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
  • 10
    • 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
  • 11
    • 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
  • 12
    • 0027175404 scopus 로고
    • Estradiol-induced effects on glutathione metabolism in rat hepatocytes
    • Ruiz, L. M., Garrido, M. J., and Lacort, M. (1993) Estradiol-induced 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
  • 13
    • 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
  • 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
  • 16
    • 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
  • 17
    • 3142518870 scopus 로고
    • Catechol estrogen oxidation and glutathione conjugation in syrian hamsters in vivo
    • Butterwonh, M., Lau, S. S., and Monks, T. J. (1995) Catechol estrogen oxidation and glutathione conjugation in syrian hamsters in vivo. The Toxicologist 15, 26.
    • (1995) The Toxicologist , vol.15 , pp. 26
    • Butterwonh, M.1    Lau, S.S.2    Monks, T.J.3
  • 18
    • 84912455172 scopus 로고
    • Mikrosomale Oxidation des Ostradiols-17B (Microsomal oxidation of 17β-estradiol. 2-Hydroxylation and formation of 1- and 4-thioethers with and without dehydrogenation of the hydroxyl group in position 17)
    • Kuss, E. (1971) Mikrosomale Oxidation des Ostradiols-17B (Microsomal oxidation of 17β-estradiol. 2-Hydroxylation and formation of 1- and 4-thioethers with and without dehydrogenation of the hydroxyl group in position 17). Hoppe-Seyler's Z. Physiol. Chem. 352, 817-836.
    • (1971) Hoppe-Seyler's Z. Physiol. Chem. , vol.352 , pp. 817-836
    • Kuss, E.1
  • 19
    • 0014511168 scopus 로고
    • Synthesis of estrogen glutathione and cysteine derivatives
    • Jellinck, P. H., and Elce, J. S. (1969) Synthesis of estrogen glutathione and cysteine derivatives. Steroids 13, 711-718.
    • (1969) Steroids , vol.13 , pp. 711-718
    • Jellinck, P.H.1    Elce, J.S.2
  • 20
    • 0027102766 scopus 로고
    • Toxicology of quinone-thioethers
    • Monks, T. J., and Lau, S. S. (1992) Toxicology of quinone-thioethers. CRC, Crit. Rev. Toxicol. 22, 243-270.
    • (1992) CRC, Crit. Rev. Toxicol. , vol.22 , pp. 243-270
    • Monks, T.J.1    Lau, S.S.2
  • 21
    • 0026510286 scopus 로고
    • 3H]17β-oestradiol 16α-hydroxylation and female-selective catechol formation
    • 3H]17β-oestradiol 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
    • 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
  • 23
    • 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
  • 24
    • 0026646133 scopus 로고
    • Catalysis of the oxidation of steroid and stilbene estrogens to estrogen quinone metabolites by the β-naphthoflavone-inducible cytochrome P450 1A family
    • Roy, D., Bernhardt, A., Strobel, H. W., and Liehr, J. G (1992) Catalysis of the oxidation of steroid and stilbene estrogens to estrogen quinone metabolites by the β-naphthoflavone-inducible cytochrome P450 1A family. Arch. Biochem. Biophys. 296, 450-456.
    • (1992) Arch. Biochem. Biophys. , vol.296 , pp. 450-456
    • Roy, D.1    Bernhardt, A.2    Strobel, H.W.3    Liehr, J.G.4
  • 25
    • 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
  • 26
    • 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
  • 27
    • 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
  • 28
    • 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
  • 29
    • 0006413771 scopus 로고
    • Synthesis and reactivity of vinyl quinone methides
    • Zanorotti, A. (1985) Synthesis and reactivity of vinyl quinone methides. J. Org. Chem. 50, 941-945.
    • (1985) J. Org. Chem. , vol.50 , pp. 941-945
    • Zanorotti, A.1
  • 31
    • 26744444428 scopus 로고
    • Studies on the preparation of the 2,3-o-quinones from 2-hydroxyoestrogens
    • Rao, P. N., and Axelrod, L. R. (1962) Studies on the preparation of the 2,3-o-quinones from 2-hydroxyoestrogens. Biochim. Biophys. Acta 60, 404-406.
    • (1962) Biochim. Biophys. Acta , vol.60 , pp. 404-406
    • Rao, P.N.1    Axelrod, L.R.2
  • 32
    • 0021721967 scopus 로고
    • Synthesis of 3,4-estrogen-o-quinone
    • Abul-Hajj, Y. J. (1984) Synthesis of 3,4-estrogen-o-quinone. J. Steroid Biochem. 21, 621-622.
    • (1984) J. Steroid Biochem. , vol.21 , pp. 621-622
    • Abul-Hajj, Y.J.1
  • 33
    • 0026078047 scopus 로고
    • Isolation of estradiol-2,3-quinone and its intermediary role in melanin formation
    • Jacobsohn, M. K. Byler, D. M., and Jacobsohn, G. M. (1991) Isolation of estradiol-2,3-quinone and its intermediary role in melanin formation. Biochim. Biophys. Acta 1073, 1-10.
    • (1991) Biochim. Biophys. Acta , vol.1073 , pp. 1-10
    • Jacobsohn, M.K.1    Byler, D.M.2    Jacobsohn, G.M.3
  • 34
    • 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
  • 35
    • 3142560550 scopus 로고
    • Biological implications of the nucleophilic addition of glutathione to quinoid compounds
    • (Vina, J., Ed.) CRC Press, Boca Raton
    • 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.
    • (1990) Glutathione: Metabolism and Physiological Functions , pp. 279-294
    • Brunmark, A.1    Cadenas, E.2
  • 36
    • 0027092534 scopus 로고
    • The enzymatic formation and chemical reactivity of quinone methides correlate with alkylphenol-induced toxicity in rat hepatocytes
    • Bolton, J. L., Vaierio, L. G. J., and Thompson, J. A. (1992) The enzymatic formation and chemical reactivity of quinone methides correlate with alkylphenol-induced toxicity in rat hepatocytes. Chem. Res. Toxicol. 5, 816-822.
    • (1992) Chem. Res. Toxicol. , vol.5 , pp. 816-822
    • Bolton, J.L.1    Vaierio, L.G.J.2    Thompson, J.A.3
  • 37
    • 0023655814 scopus 로고
    • Semiquinone anion radicals from addition of amino acids, peptides, and proteins to quinones derived from oxidation of catechols and catecholamines. An ESR stabilization study
    • Kalyanaraman, B., Premovic, P. I., and Sealy, R. C. (1987) Semiquinone anion radicals from addition of amino acids, peptides, and proteins to quinones derived from oxidation of catechols and catecholamines. An ESR stabilization study. J. Biol. Chem. 262, 11080-11087.
    • (1987) J. Biol. Chem. , vol.262 , pp. 11080-11087
    • Kalyanaraman, B.1    Premovic, P.I.2    Sealy, R.C.3
  • 38
    • 0016907344 scopus 로고
    • Potential oxidative pathways of brain catecholamines
    • Tse, D. C. S., McCreery, R. L., and Adams, R. N. (1976) Potential oxidative pathways of brain catecholamines. J. Med. Chem. 19, 37-40.
    • (1976) J. Med. Chem. , vol.19 , pp. 37-40
    • Tse, D.C.S.1    McCreery, R.L.2    Adams, R.N.3
  • 39
    • 3142631091 scopus 로고
    • Benzylic hydroxylation of 11-oxo-oestrones by hydration of quinone methides. A novel demonstration of the presence of a reactive intermediate
    • Buchan, G. M., Findlay, J. W. A., and Turner, A. B. (1975) Benzylic hydroxylation of 11-oxo-oestrones by hydration of quinone methides. A novel demonstration of the presence of a reactive intermediate. J. Chem. Soc., Chem. Commun., 126-127.
    • (1975) J. Chem. Soc., Chem. Commun. , pp. 126-127
    • Buchan, G.M.1    Findlay, J.W.A.2    Turner, A.B.3
  • 40
    • 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
  • 41
    • 0021112677 scopus 로고
    • Butylated hydroxyanisole-stimulated NADPH oxidase activity in rat liver microsomal fractions
    • Cummings, S. W., and Prough, R. A. (1983) Butylated hydroxyanisole-stimulated NADPH oxidase activity in rat liver microsomal fractions. J. Biol. Chem. 258, 12315-12319.
    • (1983) J. Biol. Chem. , vol.258 , pp. 12315-12319
    • Cummings, S.W.1    Prough, R.A.2
  • 43
    • 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
  • 44
    • 0027703513 scopus 로고
    • Reaction of quinone methides with proteins: Analysis of myoglobin adduct formation by electrospray mass spectrometry
    • Bolton, J. L., Le Blanc, J. C. Y., and Siu, K. W. M. (1993) Reaction of quinone methides with proteins: Analysis of myoglobin adduct formation by electrospray mass spectrometry. Biol. Mass Spectrom. 22, 666-668.
    • (1993) Biol. Mass Spectrom. , vol.22 , pp. 666-668
    • Bolton, J.L.1    Le Blanc, J.C.Y.2    Siu, K.W.M.3
  • 45
    • 0024376508 scopus 로고
    • Coupling of the anthracycline antitumor drug menogaril to 2′-deoxyguanosine through reductive activation
    • Egholm, M., and Koch, T. H. (1989) Coupling of the anthracycline antitumor drug menogaril to 2′-deoxyguanosine through reductive activation. J. Am. Chem. Soc. 111, 8291-8293.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 8291-8293
    • Egholm, M.1    Koch, T.H.2
  • 46
    • 3142563657 scopus 로고
    • DNA adducts of phenolic compounds resulting from the formation of quinone methide intermediates
    • Thompson, J. A., Lewis, M. A., and Bolton, J. L. (1995) DNA adducts of phenolic compounds resulting from the formation of quinone methide intermediates. The Toxicologist 15, 823.
    • (1995) The Toxicologist , vol.15 , pp. 823
    • Thompson, J.A.1    Lewis, M.A.2    Bolton, J.L.3


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