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Volumn 426, Issue 2, 2012, Pages 215-220

Molecular docking of bisphenol A and its nitrated and chlorinated metabolites onto human estrogen-related receptor-gamma

Author keywords

AutoDock 4.2 software; Bisphenol A; Estrogen receptors; Human estrogen related receptor; Metabolites of bisphenol A; Xenoestrogens

Indexed keywords

3 CHLORO 4,4' ISOPROPYLIDENEDIPHENOL; 3 NITRO 4,4' ISOPROPYLIDENEDIPHENOL; 3,3' DICHLORO 4,4' ISOPROPYLIDENEDIPHENOL; 3,3' DINITRO 4,4' ISOPROPYLIDENEDIPHENOL; 4,4' ISOPROPYLIDENEDIPHENOL; ESTRADIOL; ESTROGEN RELATED RECEPTOR GAMMA; HYPOCHLORITE; HYPOCHLOROUS ACID; PEROXYNITRITE; STEROID RECEPTOR; UNCLASSIFIED DRUG;

EID: 84866346746     PISSN: 0006291X     EISSN: 10902104     Source Type: Journal    
DOI: 10.1016/j.bbrc.2012.08.065     Document Type: Article
Times cited : (31)

References (30)
  • 3
    • 0036777477 scopus 로고    scopus 로고
    • Low doses of the endocrine disruptor bisphenol-A and the native hormone 17 beta-estradiol rapidly activate transcription factor
    • Quesada I., Fuentes E., Viso-Leon M.C., Soria B., Ripoll C., Nadal A. Low doses of the endocrine disruptor bisphenol-A and the native hormone 17 beta-estradiol rapidly activate transcription factor. Creb. Faseb. J. 2002, 16:1671-1673.
    • (2002) Creb. Faseb. J. , vol.16 , pp. 1671-1673
    • Quesada, I.1    Fuentes, E.2    Viso-Leon, M.C.3    Soria, B.4    Ripoll, C.5    Nadal, A.6
  • 4
    • 77955180574 scopus 로고    scopus 로고
    • Distinction of the binding modes for human nuclear receptor ERRγ between bisphenol A and 4-hydroxytamoxifen
    • Liu X., Matsushima A., Okada H., Shimohigashi Y. Distinction of the binding modes for human nuclear receptor ERRγ between bisphenol A and 4-hydroxytamoxifen. J. Biochem. 2010, 148:247-254.
    • (2010) J. Biochem. , vol.148 , pp. 247-254
    • Liu, X.1    Matsushima, A.2    Okada, H.3    Shimohigashi, Y.4
  • 5
  • 6
    • 15944404288 scopus 로고    scopus 로고
    • Expression and functional study of estrogen receptor-related receptors in human prostatic cells and tissues
    • Cheung C.P., Yu S., Wong K.B., Chan L.W., et al. Expression and functional study of estrogen receptor-related receptors in human prostatic cells and tissues. J. Clini. Endocrinol. Met. 2005, 90:1830-1844.
    • (2005) J. Clini. Endocrinol. Met. , vol.90 , pp. 1830-1844
    • Cheung, C.P.1    Yu, S.2    Wong, K.B.3    Chan, L.W.4
  • 7
    • 67651183897 scopus 로고    scopus 로고
    • Placenta expressing the greatest quantity of bisphenol A receptor ERRγ among the human reproductive tissues: predominant expression of type-1 ERRγ isoform
    • Takeda Y., Liu X., Sumiyoshi M., Matsushima A., Shimohigashi M., Shimohigashi Y. Placenta expressing the greatest quantity of bisphenol A receptor ERRγ among the human reproductive tissues: predominant expression of type-1 ERRγ isoform. J. Biochem. 2009, 146:113-122.
    • (2009) J. Biochem. , vol.146 , pp. 113-122
    • Takeda, Y.1    Liu, X.2    Sumiyoshi, M.3    Matsushima, A.4    Shimohigashi, M.5    Shimohigashi, Y.6
  • 8
    • 79954919689 scopus 로고    scopus 로고
    • Ipso substitution of bisphenol A catalyzed by microsomal cytochrome P450 and enhancement of estrogenic activity
    • Nakamura S., Tezuka Y., Ushiyama A., Kawashima C., et al. Ipso substitution of bisphenol A catalyzed by microsomal cytochrome P450 and enhancement of estrogenic activity. Toxicol. Lett. 2011, 203:92-95.
    • (2011) Toxicol. Lett. , vol.203 , pp. 92-95
    • Nakamura, S.1    Tezuka, Y.2    Ushiyama, A.3    Kawashima, C.4
  • 9
    • 1542791534 scopus 로고    scopus 로고
    • Potent estrogenic metabolites of bisphenol A and bisphenol B formed by rat liver S9 fraction: their structures and estrogenic potency
    • Yoshihara S., Mizutare T., Makishima M., Suzuki N., Fujimoto N., Igarashi K., Ohta S. Potent estrogenic metabolites of bisphenol A and bisphenol B formed by rat liver S9 fraction: their structures and estrogenic potency. Toxicol. Sci. 2004, 78:50-59.
    • (2004) Toxicol. Sci. , vol.78 , pp. 50-59
    • Yoshihara, S.1    Mizutare, T.2    Makishima, M.3    Suzuki, N.4    Fujimoto, N.5    Igarashi, K.6    Ohta, S.7
  • 10
    • 0034903393 scopus 로고    scopus 로고
    • Identification and quantification of chlorinated bisphenol A in wastewater from wastepaper recycling plants
    • Fukazawaa H., Hoshinoa K., Shiozawaa T., Matsushitab H., Teraoa Y. Identification and quantification of chlorinated bisphenol A in wastewater from wastepaper recycling plants. Chemosphere 2001, 44:973-979.
    • (2001) Chemosphere , vol.44 , pp. 973-979
    • Fukazawaa, H.1    Hoshinoa, K.2    Shiozawaa, T.3    Matsushitab, H.4    Teraoa, Y.5
  • 11
    • 2942699918 scopus 로고    scopus 로고
    • Chlorination of bisphenol A: kinetics and by-products formation
    • Gallard H., Leclercq A., Croué J.P. Chlorination of bisphenol A: kinetics and by-products formation. Chemosphere 2004, 56:465-473.
    • (2004) Chemosphere , vol.56 , pp. 465-473
    • Gallard, H.1    Leclercq, A.2    Croué, J.P.3
  • 13
    • 0029953744 scopus 로고    scopus 로고
    • Nitric oxide and peroxynitrite. Mechanism of carbon dioxide-catalyzed oxidation of tyrosine by peroxynitrite
    • Lymar S.V., Jiang Q., Hurst J.K. Nitric oxide and peroxynitrite. Mechanism of carbon dioxide-catalyzed oxidation of tyrosine by peroxynitrite. Biochemistry 1996, 35:7855-7861.
    • (1996) Biochemistry , vol.35 , pp. 7855-7861
    • Lymar, S.V.1    Jiang, Q.2    Hurst, J.K.3
  • 14
    • 0030249458 scopus 로고    scopus 로고
    • Peroxynitrite reaction with carbon dioxide/bicarbonate: kinetics and influence on peroxynitrite-mediated oxidations
    • Denicola A., Freeman B.A., Trujillo M., Radi R. Peroxynitrite reaction with carbon dioxide/bicarbonate: kinetics and influence on peroxynitrite-mediated oxidations. Arch. Biochem. Biophys. 1996, 333:49-58.
    • (1996) Arch. Biochem. Biophys. , vol.333 , pp. 49-58
    • Denicola, A.1    Freeman, B.A.2    Trujillo, M.3    Radi, R.4
  • 15
    • 50649102183 scopus 로고    scopus 로고
    • Genotoxicity and estrogenic activity of 3,3'-dinitrobisphenol A in goldfish
    • Toyoizumi T., Deguchi Y., Masuda S., Kinae N. Genotoxicity and estrogenic activity of 3,3'-dinitrobisphenol A in goldfish. Biosci. Biotech. Biochem. 2008, 72:2118-2123.
    • (2008) Biosci. Biotech. Biochem. , vol.72 , pp. 2118-2123
    • Toyoizumi, T.1    Deguchi, Y.2    Masuda, S.3    Kinae, N.4
  • 16
    • 22144472574 scopus 로고    scopus 로고
    • Changes in the mutagenic and estrogenic activities of bisphenol A upon treatment with nitrite
    • Masuda S., Terashima Y., Sano A., Kuruto R., et al. Changes in the mutagenic and estrogenic activities of bisphenol A upon treatment with nitrite. Mut. Res. 2005, 585:137-146.
    • (2005) Mut. Res. , vol.585 , pp. 137-146
    • Masuda, S.1    Terashima, Y.2    Sano, A.3    Kuruto, R.4
  • 17
    • 10444243407 scopus 로고    scopus 로고
    • In vitro and in vivo estrogenic activity of chlorinated derivatives of bisphenol A
    • Takemura H., Ma J., Sayama K., Terao Y., Zhu B.T., Shimoi K. In vitro and in vivo estrogenic activity of chlorinated derivatives of bisphenol A. Toxicology 2005, 207:215-221.
    • (2005) Toxicology , vol.207 , pp. 215-221
    • Takemura, H.1    Ma, J.2    Sayama, K.3    Terao, Y.4    Zhu, B.T.5    Shimoi, K.6
  • 18
    • 33745203244 scopus 로고    scopus 로고
    • Synthesis of peroxynitrite using isoamyl nitrite and hydrogen peroxide in a homogeneous solvent system
    • Uppu R.M. Synthesis of peroxynitrite using isoamyl nitrite and hydrogen peroxide in a homogeneous solvent system. Anal. Biochem. 2006, 354:165-168.
    • (2006) Anal. Biochem. , vol.354 , pp. 165-168
    • Uppu, R.M.1
  • 20
    • 8544251150 scopus 로고
    • The acid ionization constant of HOCl from 5 to 35°C
    • Morris J.C. The acid ionization constant of HOCl from 5 to 35°C. J. Phys. Chem. 1966, 70:3798-3805.
    • (1966) J. Phys. Chem. , vol.70 , pp. 3798-3805
    • Morris, J.C.1
  • 22
    • 0029867717 scopus 로고    scopus 로고
    • Acceleration of peroxynitrite oxidations by carbon dioxide
    • Uppu R.M., Squadrito G.L., Pryor W.A. Acceleration of peroxynitrite oxidations by carbon dioxide. Arch. Biochem. Biophys. 1996, 327:335-343.
    • (1996) Arch. Biochem. Biophys. , vol.327 , pp. 335-343
    • Uppu, R.M.1    Squadrito, G.L.2    Pryor, W.A.3
  • 23
    • 65449183418 scopus 로고    scopus 로고
    • Using acidic ionic liquid 1- butyl-3-methylimidazolium hydrogen sulfate in selective nitration of phenols under mild conditions
    • Tajik H., Niknam K., Parsa F. Using acidic ionic liquid 1- butyl-3-methylimidazolium hydrogen sulfate in selective nitration of phenols under mild conditions. J. Iran. Chem. Soc. 2009, 6:159-164.
    • (2009) J. Iran. Chem. Soc. , vol.6 , pp. 159-164
    • Tajik, H.1    Niknam, K.2    Parsa, F.3
  • 25
    • 0036558058 scopus 로고    scopus 로고
    • Products of aqueous chlorination of bisphenol A and their estrogenic activity
    • Hu J.-Y., Aizawa T., Ookubo S. Products of aqueous chlorination of bisphenol A and their estrogenic activity. Environ. Sci. Technol. 2002, 36:1980-1987.
    • (2002) Environ. Sci. Technol. , vol.36 , pp. 1980-1987
    • Hu, J.-Y.1    Aizawa, T.2    Ookubo, S.3
  • 26
    • 0027222826 scopus 로고
    • Bisphenol-A: an estrogenic substance is released from polycarbonate flasks during autoclaving
    • Krishnan A.V., Stathis P., Permuth S.F., Tokes L., Feldman D. Bisphenol-A: an estrogenic substance is released from polycarbonate flasks during autoclaving. Endocrinology 1993, 132:2279-2286.
    • (1993) Endocrinology , vol.132 , pp. 2279-2286
    • Krishnan, A.V.1    Stathis, P.2    Permuth, S.F.3    Tokes, L.4    Feldman, D.5
  • 27
    • 84866397661 scopus 로고    scopus 로고
    • Metabolism and Toxicokinetics of Bisphenol A. FAO/WHO Expert Meeting on Bisphenol A,
    • D. R. Doerge, and Fisher, J. W. Metabolism and Toxicokinetics of Bisphenol A. FAO/WHO Expert Meeting on Bisphenol A, (2010).
    • (2010)
    • Doerge, D.R.1    Fisher, J.W.2
  • 28
    • 33748688829 scopus 로고    scopus 로고
    • Toxicokinetics of bisphenol A in pregnant DA/Han rats after single i.v. application
    • Moors S., Diel P., Degen G.H. Toxicokinetics of bisphenol A in pregnant DA/Han rats after single i.v. application. Arch. Toxicol. 2006, 80:647-655.
    • (2006) Arch. Toxicol. , vol.80 , pp. 647-655
    • Moors, S.1    Diel, P.2    Degen, G.H.3
  • 29
    • 0036841276 scopus 로고    scopus 로고
    • Metabolism of bisphenol A in primary cultured hepatocytes from mice, rats, and humans
    • Pritchett J.J., Kuester R.K., Sipes I.G. Metabolism of bisphenol A in primary cultured hepatocytes from mice, rats, and humans. Drug Metab. Dispos. 2002, 30:1180-1185.
    • (2002) Drug Metab. Dispos. , vol.30 , pp. 1180-1185
    • Pritchett, J.J.1    Kuester, R.K.2    Sipes, I.G.3
  • 30
    • 0036802304 scopus 로고    scopus 로고
    • Metabolism and kinetics of bisphenol A in humans at low doses following oral administration
    • Volkel W., Colnot T., Csanady G.A., Filser J.G., Dekant W. Metabolism and kinetics of bisphenol A in humans at low doses following oral administration. Chem. Res. Toxicol. 2002, 15:1281-1287.
    • (2002) Chem. Res. Toxicol. , vol.15 , pp. 1281-1287
    • Volkel, W.1    Colnot, T.2    Csanady, G.A.3    Filser, J.G.4    Dekant, W.5


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