메뉴 건너뛰기




Volumn 16, Issue 6, 2003, Pages 695-707

Conformations of stereoisomeric base adducts to 4-Hydroxyequilenin

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINOPURINE; 4 HYDROXYEQUILENIN; ADENINE; CATECHOL ESTROGEN; CONJUGATED ESTROGEN; CYTOSINE; DEOXYADENOSINE; DEOXYCYTIDINE; DNA BASE; DOUBLE STRANDED DNA; DRUG METABOLITE; EQUILENIN; EQUILIN; GUANINE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0037636061     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx0340246     Document Type: Article
Times cited : (18)

References (41)
  • 1
    • 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
    • 0027717576 scopus 로고
    • Clinical management of women at increased risk for breast cancer
    • Vogel, V. G., Yeomeans, A., and Higginbotham, E. (1993) Clinical management of women at increased risk for breast cancer. Breast Cancer Res. Treat. 28, 195-210.
    • (1993) Breast Cancer Res. Treat. , vol.28 , pp. 195-210
    • Vogel, V.G.1    Yeomeans, A.2    Higginbotham, E.3
  • 6
    • 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
  • 7
    • 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
  • 8
    • 0031741669 scopus 로고    scopus 로고
    • Role of quinoids in estrogen carcinogenesis
    • Bolton, J. L., Pisha, E., Zhang, F., and Qiu, S. (1998) Role of quinoids in estrogen carcinogenesis. Chem. Res. Toxicol. 11, 1113-1127.
    • (1998) Chem. Res. Toxicol. , vol.11 , pp. 1113-1127
    • Bolton, J.L.1    Pisha, E.2    Zhang, F.3    Qiu, S.4
  • 10
    • 0032973129 scopus 로고    scopus 로고
    • The major metabolite of equilin, 4-hydroxyequilin autoxidizes to an o-quinone which isomerizes to the potent cytotoxin 4-hydroxyequilenin-o-quinone
    • Zhang, F., Chen, Y., Pisha, E., Shen, L., Xiong, Y., van Breemen, R. B., and Bolton, J. L. (1999) The major metabolite of equilin, 4-hydroxyequilin autoxidizes to an o-quinone which isomerizes to the potent cytotoxin 4-hydroxyequilenin-o-quinone. Chem. Res. Toxicol. 12, 204-213.
    • (1999) Chem. Res. Toxicol. , vol.12 , pp. 204-213
    • Zhang, F.1    Chen, Y.2    Pisha, E.3    Shen, L.4    Xiong, Y.5    Van Breemen, R.B.6    Bolton, J.L.7
  • 11
    • 0036680017 scopus 로고    scopus 로고
    • Quinoids, quinoid radicals, and phenoxyl radicals formed from estrogens and antiestrogens
    • Bolton, J. L. (2002) Quinoids, quinoid radicals, and phenoxyl radicals formed from estrogens and antiestrogens. Toxicology 177 (1), 55-65.
    • (2002) Toxicology , vol.177 , Issue.1 , pp. 55-65
    • Bolton, J.L.1
  • 13
    • 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
  • 14
    • 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
  • 15
    • 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
  • 16
    • 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., Alam, 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    Alam, Z.6    Van Breemen, R.B.7    Bolton, J.L.8
  • 18
    • 0034746710 scopus 로고    scopus 로고
    • Evidence that a metabolite of equine estrogens, 4-hydroxyequilenin, induces cellular transformation in vitro
    • Pisha, E., Lui, X., Constantinou, A. I., and Bolton, J. L. (2001) Evidence that a metabolite of equine estrogens, 4-hydroxyequilenin, induces cellular transformation in vitro. Chem. Res. Toxicol. 14, 82-90.
    • (2001) Chem. Res. Toxicol. , vol.14 , pp. 82-90
    • Pisha, E.1    Lui, X.2    Constantinou, A.I.3    Bolton, J.L.4
  • 19
    • 0035659961 scopus 로고    scopus 로고
    • Equine estrogen metabolite 4-Hydroxyequilenin induces DNA damage in the rat mammary tissues: Formation of single-strand breaks, apurinic sites, stable adducts, and oxidized bases
    • Zhang, F., Swanson, S. M., van Breeman, R. B., Liu, X., Yang, Y., Gu, C., and Bolton, J. L. (2001) Equine estrogen metabolite 4-Hydroxyequilenin induces DNA damage in the rat mammary tissues: formation of single-strand breaks, apurinic sites, stable adducts, and oxidized bases. Chem. Res. Toxicol. 14, 1654-1659.
    • (2001) Chem. Res. Toxicol. , vol.14 , pp. 1654-1659
    • Zhang, F.1    Swanson, S.M.2    Van Breeman, R.B.3    Liu, X.4    Yang, Y.5    Gu, C.6    Bolton, J.L.7
  • 20
    • 0029938649 scopus 로고    scopus 로고
    • The role of adduct site-specific mutagenesis in understanding how carcinogen-DNA adducts cause mutations: Perspective, prospects and problems
    • Loechler, E. L. (1996) The role of adduct site-specific mutagenesis in understanding how carcinogen-DNA adducts cause mutations: perspective, prospects and problems. Carcinogenesis 17, 895-902.
    • (1996) Carcinogenesis , vol.17 , pp. 895-902
    • Loechler, E.L.1
  • 21
    • 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
  • 22
    • 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, R.B.5    Nikolic, D.6    Bolton, J.L.7
  • 23
    • 0034744758 scopus 로고    scopus 로고
    • Equilenin-2′-deoxynucleoside adducts: Analysis with nanoliquid chromatography coupled to nano-eletrospray tandem mass spectrometry
    • Embrechts, J., Lemiere, F., Van Dongen, W., and Esmans, E. L. (2001) Equilenin-2′-deoxynucleoside adducts: analysis with nanoliquid chromatography coupled to nano-eletrospray tandem mass spectrometry. J. Mass Spectrom. 36, 317-328.
    • (2001) J. Mass Spectrom. , vol.36 , pp. 317-328
    • Embrechts, J.1    Lemiere, F.2    Van Dongen, W.3    Esmans, E.L.4
  • 24
    • 0036093235 scopus 로고    scopus 로고
    • Conformational analysis of a 4-hydroxyequilenin guanine adduct using density function theory
    • Yan, S., Min, W., Ding, S., Geacintov, N. E., and Broyde, S. (2002) Conformational analysis ofa 4-hydroxyequilenin guanine adduct using density function theory Chem. Res. Toxicol. 15, 648-653.
    • (2002) Chem. Res. Toxicol. , vol.15 , pp. 648-653
    • Yan, S.1    Min, W.2    Ding, S.3    Geacintov, N.E.4    Broyde, S.5
  • 25
    • 0032755401 scopus 로고    scopus 로고
    • 5-3-ketosteroid isomerase from Pseudomonas testosteroni in complex with equilenin settles the correct hydrogen bonding scheme for transition state stabilization
    • 5-3-ketosteroid isomerase from Pseudomonas testosteroni in complex with equilenin settles the correct hydrogen bonding scheme for transition state stabilization. J. Biol. Chem. 17, 32863-32868.
    • (1999) J. Biol. Chem. , vol.17 , pp. 32863-32868
    • Cho, H.-S.1    Ha, N.-C.2    Choi, G.3    Kim, H.-J.4    Lee, D.5    Oh, K.S.6    Kim, K.S.7    Lee, W.8    Choi, K.Y.9    Oh, B.-H.10
  • 26
    • 0037571112 scopus 로고    scopus 로고
    • Merck molecular force field. I. Basis, form, scope, parametrization and performance of MMFF94
    • Halgren, T. A. (1996) Merck Molecular Force Field. I. Basis, Form, Scope, Parametrization and Performance of MMFF94. J. Comput. Chem. 17, 490-519.
    • (1996) J. Comput. Chem. , vol.17 , pp. 490-519
    • Halgren, T.A.1
  • 27
    • 0011134241 scopus 로고    scopus 로고
    • Merck molecular force field. II. MMFF94 van der Waals and electrostatic parameters for intermolecular interactions
    • Halgren, T. A. (1996) Merck Molecular Force Field. II. MMFF94 van der Waals and Electrostatic Parameters for Intermolecular Interactions. J. Comput. Chem. 17, 520-552.
    • (1996) J. Comput. Chem. , vol.17 , pp. 520-552
    • Halgren, T.A.1
  • 28
    • 0011143599 scopus 로고    scopus 로고
    • Merck molecular force field. III. Molecular geometrics and vibrational frequencies for MMFF94
    • Halgren, T. A. (1996) Merck Molecular Force Field. III. Molecular Geometrics and Vibrational Frequencies for MMFF94. J. Comput. Chem. 17, 553-586.
    • (1996) J. Comput. Chem. , vol.17 , pp. 553-586
    • Halgren, T.A.1
  • 29
    • 0001061464 scopus 로고    scopus 로고
    • Merck molecular force field. IV. Conformational energies and geometries
    • Halgren, T. A., and Nachbar, R. B. (1996) Merck Molecular Force Field. IV. Conformational Energies and Geometries. J. Comput. Chem. 17, 587-615.
    • (1996) J. Comput. Chem. , vol.17 , pp. 587-615
    • Halgren, T.A.1    Nachbar, R.B.2
  • 30
    • 0000189651 scopus 로고
    • Density-functional thermochemistry. III. The role of exact exchange
    • Becke, A. D. (1993) Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 98, 5648-5652.
    • (1993) J. Chem. Phys. , vol.98 , pp. 5648-5652
    • Becke, A.D.1
  • 31
    • 4243553426 scopus 로고
    • Density-functional exchange-energy approximation with correct asymptotic behavior
    • Becke, A. D. (1988) Density-functional exchange-energy approximation with correct asymptotic behavior. Phys. Rev. A 38, 3098-3100.
    • (1988) Phys. Rev. A , vol.38 , pp. 3098-3100
    • Becke, A.D.1
  • 32
    • 0345491105 scopus 로고
    • Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density
    • Lee, C., Yang, W., and Parr, R. G. (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B 37, 785-789.
    • (1988) Phys. Rev. B , vol.37 , pp. 785-789
    • Lee, C.1    Yang, W.2    Parr, R.G.3
  • 33
    • 0000216001 scopus 로고
    • Accurate spindependent electron liquid correlation energies for local spin density calculations: A critical analysis
    • Vosko, S. H., Wilk, L., and Nusair, M. (1980) Accurate spindependent electron liquid correlation energies for local spin density calculations: a critical analysis. Can. J. Phys. 58, 1200-1211.
    • (1980) Can. J. Phys. , vol.58 , pp. 1200-1211
    • Vosko, S.H.1    Wilk, L.2    Nusair, M.3
  • 35
    • 33748542524 scopus 로고
    • Allylic strain in six-membered rings
    • Johnson, F. (1968) Allylic strain in six-membered rings. Chem Rev. 68, 375-413.
    • (1968) Chem. Rev. , vol.68 , pp. 375-413
    • Johnson, F.1
  • 37
    • 0031041812 scopus 로고    scopus 로고
    • NMR solution structures of stereoisometric covalent polycyclic aromatic carcinogen-DNA adduct: Principles, patterns, and diversity
    • Geacintov, N. E., Cosman, M., Hingerty, B. E., Amin, S., Broyde, S., and Patel, D. J. (1997) NMR solution structures of stereoisometric covalent polycyclic aromatic carcinogen-DNA adduct: principles, patterns, and diversity. Chem. Res. Toxicol. 10, 111-146.
    • (1997) Chem. Res. Toxicol. , vol.10 , pp. 111-146
    • Geacintov, N.E.1    Cosman, M.2    Hingerty, B.E.3    Amin, S.4    Broyde, S.5    Patel, D.J.6
  • 38
    • 0037163036 scopus 로고    scopus 로고
    • Trans-Lesion synthesis past bulky benzo [a] pyrene diol epoxide N2-dG and N6-dA lesions catalyzed by DNA bypass polymerases
    • Rechkoblit, O., Zhang, Y., Guo, D., Wang, Z., Amin, S., Krzeminsky, J., Louneva, N., and Geacintov, N. E. (2002) trans-Lesion synthesis past bulky benzo [a] pyrene diol epoxide N2-dG and N6-dA lesions catalyzed by DNA bypass polymerases. J. Biol. Chem. 277, 30488-30494.
    • (2002) J. Biol. Chem. , vol.277 , pp. 30488-30494
    • Rechkoblit, O.1    Zhang, Y.2    Guo, D.3    Wang, Z.4    Amin, S.5    Krzeminsky, J.6    Louneva, N.7    Geacintov, N.E.8
  • 39
    • 0037023677 scopus 로고    scopus 로고
    • Preferential misincorporation of purine nucleotides by human DNA polymerase eta opposite benzo[a]pyrene 7,8-diol 9,10-epoxide deoxyguanosine adducts
    • Chiapperino, D., Kroth, H., Kramarczuk, I. H., Sayer, J. M., Masutani, C., Hanaoka, F., Jerina, D. M., and Cheh, A. M. (2002) Preferential misincorporation of purine nucleotides by human DNA polymerase eta opposite benzo[a]pyrene 7,8-diol 9,10-epoxide deoxyguanosine adducts. J. Biol. Chem. 277, 11765-11771.
    • (2002) J. Biol. Chem. , vol.277 , pp. 11765-11771
    • Chiapperino, D.1    Kroth, H.2    Kramarczuk, I.H.3    Sayer, J.M.4    Masutani, C.5    Hanaoka, F.6    Jerina, D.M.7    Cheh, A.M.8
  • 40
    • 0034029834 scopus 로고    scopus 로고
    • Unrepaired fjord region polycyclic aromatic hydrocarbon-DNA adducts in ras codon 61 mutational hot spots
    • Buterin, T., Hess, M. T., Luneva, N., Geacintov, N. E., Amin, S., Kroth, H., Seidel, A., and Naegeli, H. (2000) Unrepaired fjord region polycyclic aromatic hydrocarbon-DNA adducts in ras codon 61 mutational hot spots. Cancer Res. 60, 1849-1856.
    • (2000) Cancer Res. , vol.60 , pp. 1849-1856
    • Buterin, T.1    Hess, M.T.2    Luneva, N.3    Geacintov, N.E.4    Amin, S.5    Kroth, H.6    Seidel, A.7    Naegeli, H.8
  • 41
    • 0037027367 scopus 로고    scopus 로고
    • Thermodynamic and structural factors in the removal of bulky DNA adducts by the nucleotide excision repair machinery
    • Geacintov, N. E., Broyde, S., Buterin, T., Naegeli, H., Wu, M., Yan, S., and Patel, D. J. (2002) Thermodynamic and structural factors in the removal of bulky DNA adducts by the nucleotide excision repair machinery. Biopolymers 65, 202-210.
    • (2002) Biopolymers , vol.65 , pp. 202-210
    • Geacintov, N.E.1    Broyde, S.2    Buterin, T.3    Naegeli, H.4    Wu, M.5    Yan, S.6    Patel, D.J.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.