메뉴 건너뛰기




Volumn 48, Issue 30, 2009, Pages 7098-7109

NMR and computational studies of stereoisomeric equine estrogen-derived DNA cytidine adducts in oligonucleotide duplexes: Opposite orientations of diastereomeric forms

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE COMPONENTS; AQUEOUS SOLUTIONS; CELLULAR ENVIRONMENT; COMPLEMENTARY STRAND; COMPUTATIONAL APPROACH; COMPUTATIONAL STUDIES; CYTIDINE; DIASTEREOMERIC; DNA ADDUCTS; DNA DUPLEXES; DNA LESIONS; DOUBLE-HELICAL STRUCTURES; GLYCOSIDIC BOND; HORMONE REPLACEMENT THERAPY; HYDROXYL GROUPS; IN-VITRO; METABOLIC ACTIVATION; MINOR GROOVES; MODIFIED OLIGONUCLEOTIDES; OLIGONUCLEOTIDE DUPLEXES; PREMARIN; WATSON-CRICK PAIRING;

EID: 68049101976     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi9006429     Document Type: Article
Times cited : (8)

References (40)
  • 1
    • 0346599193 scopus 로고    scopus 로고
    • National use of postmenopausal hormone therapy: Annual trends and response to recent evidence
    • Hersh, A. L., Stefanick,M. L., and Stafford, R. S. (2004) National use of postmenopausal hormone therapy: annual trends and response to recent evidence. JAMA, J. Am. Med. Assoc. 291, 47-53.
    • (2004) JAMA, J. Am. Med. Assoc. , vol.291 , pp. 47-53
    • Hersh, A.L.1    Stefanick, M.L.2    Stafford, R.S.3
  • 4
    • 30944469849 scopus 로고    scopus 로고
    • Mechanisms of disease: Estrogen carcinogenesis in breast cancer
    • Yager, J. D., and Davidson, N. E. (2006) Mechanisms of disease: Estrogen carcinogenesis in breast cancer. N. Engl. J. Med. 354, 270-282.
    • (2006) N. Engl. J. Med. , vol.354 , pp. 270-282
    • Yager, J.D.1    Davidson, N.E.2
  • 6
    • 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, 55-65.
    • (2002) Toxicology , vol.177 , pp. 55-65
    • Bolton, J.L.1
  • 7
    • 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
  • 8
    • 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. X., vanBreemen, R. B., Zhang, F. G., Chen, Y. M., 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.X.2    VanBreemen, R.B.3    Zhang, F.G.4    Chen, Y.M.5    Bolton, J.L.6
  • 9
    • 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
  • 10
    • 0034744758 scopus 로고    scopus 로고
    • Equilenin-2′-deoxynucleoside adducts: Analysis with nano-liquid chromatography coupled to nano-electrospray tandem mass spectrometry
    • DOI 10.1002/jms.136
    • Embrechts, J., Lemiere, F., Van Dongen, W., and Esmans, E. L. (2001) Equilenin-2′-deoxynucleoside adducts: analysis with nano-liquid chromatography coupled to nano-electrospray tandem mass spectrometry. J. Mass Spectrom. 36, 317-328. (Pubitemid 32280197)
    • (2001) Journal of Mass Spectrometry , vol.36 , Issue.3 , pp. 317-328
    • Embrechts, J.1    Lemire, F.2    Van Dongen, W.3    Esmans, E.L.4
  • 11
    • 27644463404 scopus 로고    scopus 로고
    • Base selectivity and effects of sequence and DNA secondary structure on the formation of covalent adducts derived from the equine estrogen metabolite 4-hydroxyequilenin
    • Kolbanovskiy, A., Kuzmin, V., Shastry, A., Kolbanovskaya, M., Chen, D., Chang, M., Bolton, J. L., and Geacintov, N. E. (2005) Base selectivity and effects of sequence and DNA secondary structure on the formation of covalent adducts derived from the equine estrogen metabolite 4-hydroxyequilenin. Chem. Res. Toxicol. 18, 1737-1747.
    • (2005) Chem. Res. Toxicol. , vol.18 , pp. 1737-1747
    • Kolbanovskiy, A.1    Kuzmin, V.2    Shastry, A.3    Kolbanovskaya, M.4    Chen, D.5    Chang, M.6    Bolton, J.L.7    Geacintov, N.E.8
  • 12
    • 38949118229 scopus 로고    scopus 로고
    • Potential mechanisms of estrogen quinone carcinogenesis
    • Bolton, J. L., and Thatcher, G. R. (2008) Potential mechanisms of estrogen quinone carcinogenesis. Chem. Res. Toxicol. 21, 93-101.
    • (2008) Chem. Res. Toxicol. , vol.21 , pp. 93-101
    • Bolton, J.L.1    Thatcher, G.R.2
  • 13
    • 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 Breemen, 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 Breemen, R.B.3    Liu, X.4    Yang, Y.5    Gu, C.6    Bolton, J.L.7
  • 14
    • 0037487092 scopus 로고    scopus 로고
    • Detection of estrogen DNA-adducts in human breast tumor tissue and healthy tissue by combined nano LC-nano ES tandem mass spectrometry
    • Embrechts, J., Lemiere, F., Van Dongen, W., Esmans, E. L., Buytaert, P., Van Marck, E., Kockx, M., and Makar, A. (2003) Detection of estrogen DNA-adducts in human breast tumor tissue and healthy tissue by combined nano LC-nano ES tandem mass spectrometry. J. Am. Soc. Mass Spectrom. 14, 482-491.
    • (2003) J. Am. Soc. Mass Spectrom. , vol.14 , pp. 482-491
    • Embrechts, J.1    Lemiere, F.2    Van Dongen, W.3    Esmans, E.L.4    Buytaert, P.5    Van Marck, E.6    Kockx, M.7    Makar, A.8
  • 15
    • 4444220496 scopus 로고    scopus 로고
    • Translesion synthesis past equine estrogen-derived 2′-deoxycytidine DNA adducts by human DNA polymerases η and κ
    • DOI 10.1021/bi049273n
    • Suzuki, N., Yasui, M., Santosh Laxmi, Y. R., Ohmori, H., Hanaoka, F., and Shibutani, S. (2004) Translesion synthesis past equine estrogen-derived 2′-deoxycytidine DNA adducts by human DNA polymerases eta and kappa. Biochemistry 43, 11312-11320. (Pubitemid 39180375)
    • (2004) Biochemistry , vol.43 , Issue.35 , pp. 11312-11320
    • Suzuki, N.1    Yasui, M.2    Laxmi, Y.R.S.3    Ohmori, H.4    Hanaoka, F.5    Shibutani, S.6
  • 16
    • 33646592905 scopus 로고    scopus 로고
    • Translesion synthesis past equine estrogen-derived 2′- deoxyadenosine DNA adducts by human DNA polymerases η and κ
    • DOI 10.1021/bi0525324
    • Yasui, M., Laxmi, Y. R., Ananthoju, S. R., Suzuki, N., Kim, S. Y., and Shibutani, S. (2006) Translesion synthesis past equine estrogen-derived 20-deoxyadenosine DNA adducts by human DNA polymerases eta and kappa. Biochemistry 45, 6187-6194. (Pubitemid 43727111)
    • (2006) Biochemistry , vol.45 , Issue.19 , pp. 6187-6194
    • Yasui, M.1    Laxmi, Y.R.S.2    Ananthoju, S.R.3    Suzuki, N.4    Kim, S.Y.5    Shibutani, S.6
  • 17
    • 53549113331 scopus 로고    scopus 로고
    • Determination of absolute configurations of 4-hydroxyequilenin-cytosine and -adenine adducts by optical rotatory dispersion, electronic circular dichroism, density functional theory calculations, and mass spectrometry
    • Ding, S., Wang, Y., Kolbanovskiy, A., Durandin, A., Bolton, J. L., van Breemen, R. B., Broyde, S., and Geacintov, N. E. (2008) Determination of absolute configurations of 4-hydroxyequilenin-cytosine and -adenine adducts by optical rotatory dispersion, electronic circular dichroism, density functional theory calculations, and mass spectrometry. Chem. Res. Toxicol. 21, 1739-1748.
    • (2008) Chem. Res. Toxicol. , vol.21 , pp. 1739-1748
    • Ding, S.1    Wang, Y.2    Kolbanovskiy, A.3    Durandin, A.4    Bolton, J.L.5    Van Breemen, R.B.6    Broyde, S.7    Geacintov, N.E.8
  • 18
    • 0037636061 scopus 로고    scopus 로고
    • Conformations of stereoisomeric base adducts to 4-hydroxyequilenin
    • Ding, S., Shapiro, R., Geacintov, N. E., and Broyde, S. (2003) Conformations of stereoisomeric base adducts to 4-hydroxyequilenin. Chem. Res. Toxicol. 16, 695-707.
    • (2003) Chem. Res. Toxicol. , vol.16 , pp. 695-707
    • Ding, S.1    Shapiro, R.2    Geacintov, N.E.3    Broyde, S.4
  • 19
    • 27644502314 scopus 로고    scopus 로고
    • Equilenin-derived DNA adducts to cytosine in DNA duplexes: Structures and thermodynamics
    • DOI 10.1021/bi051090t
    • Ding, S., Shapiro, R., Geacintov, N. E., and Broyde, S. (2005) Equilenin-derived DNA adducts to cytosine in DNA duplexes: structures and thermodynamics. Biochemistry 44, 14565-14576. (Pubitemid 41567464)
    • (2005) Biochemistry , vol.44 , Issue.44 , pp. 14565-14576
    • Ding, S.1    Shapiro, R.2    Geacintov, N.E.3    Broyde, S.4
  • 20
    • 33846139338 scopus 로고    scopus 로고
    • 4-Hydroxyequilenin-adenine lesions in DNA duplexes: Stereochemistry, damage site, and structure
    • DOI 10.1021/bi061652o
    • Ding, S., Shapiro, R., Geacintov, N. E., and Broyde, S. (2007) 4-hydroxyequilenin-adenine lesions in DNA duplexes: stereochemistry, damage site, and structure. Biochemistry 46, 182-191. (Pubitemid 46075022)
    • (2007) Biochemistry , vol.46 , Issue.1 , pp. 182-191
    • Ding, S.1    Shapiro, R.2    Geacintov, N.E.3    Broyde, S.4
  • 21
    • 47549092381 scopus 로고    scopus 로고
    • Conformational properties of equilenin-DNA adducts: Stereoisomer and base effects
    • Ding, S., Shapiro, R., Cai, Y., Geacintov,N. E., and Broyde, S. (2008) Conformational properties of equilenin-DNA adducts: stereoisomer and base effects. Chem. Res. Toxicol. 21, 1064-1073.
    • (2008) Chem. Res. Toxicol. , vol.21 , pp. 1064-1073
    • Ding, S.1    Shapiro, R.2    Cai, Y.3    Geacintov, N.E.4    Broyde, S.5
  • 23
    • 27644524638 scopus 로고    scopus 로고
    • Translesion synthesis and nucleotide excision repair of site specifically modified oligodeoxyribonucleotides containing single lesions derived from the equine estrogen metabolite 4-OHEN
    • Chen, D. D., Oum, L., Kolbanovskiy, A., Kuzmin, V., Shastry, A., Chang, M. S., Bolton, J. L., and Geacintov, N. (2004) Translesion synthesis and nucleotide excision repair of site specifically modified oligodeoxyribonucleotides containing single lesions derived from the equine estrogen metabolite 4-OHEN. Chem. Res. Toxicol. 17, 1782-11782
    • (2004) Chem. Res. Toxicol. , vol.17 , pp. 1782-11782
    • Chen, D.D.1    Oum, L.2    Kolbanovskiy, A.3    Kuzmin, V.4    Shastry, A.5    Chang, M.S.6    Bolton, J.L.7    Geacintov, N.8
  • 24
    • 57749188239 scopus 로고    scopus 로고
    • Differential nucleotide excision repair susceptibility of bulky DNA adducts in different sequence contexts: Hierarchies of recognition signals
    • Cai, Y., Patel, D. J., Geacintov, N. E., and Broyde, S. (2009) Differential nucleotide excision repair susceptibility of bulky DNA adducts in different sequence contexts: hierarchies of recognition signals. J. Mol. Biol. 385, 30-44.
    • (2009) J. Mol. Biol. , vol.385 , pp. 30-44
    • Cai, Y.1    Patel, D.J.2    Geacintov, N.E.3    Broyde, S.4
  • 25
    • 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. X., 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.X.6    Patel, D.J.7
  • 27
    • 0032560959 scopus 로고    scopus 로고
    • Continuum solvent studies of the stability of DNA, RNA, and phosphoramidate-DNA helices
    • Srinivasan, J., Cheatham, T. E., Cieplak, P., Kollman, P. A., and Case, D. A. (1998) Continuum solvent studies of the stability of DNA, RNA, and phosphoramidate-DNA helices. J. Am. Chem. Soc. 120, 9401-9409.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 9401-9409
    • Srinivasan, J.1    Cheatham, T.E.2    Cieplak, P.3    Kollman, P.A.4    Case, D.A.5
  • 29
    • 0003023614 scopus 로고
    • MOIL-View - A program for visualization of structure and dynamics of biomolecules and STO - A program for computing stochastic paths
    • (Pullman, A., Ed.) Kluwer, Amsterdam, The Netherlands
    • Simmerling, C., Elber, R., and Zhang, J. (1995) MOIL-View - a program for visualization of structure and dynamics of biomolecules and STO - a program for computing stochastic paths, in Modeling of Biomolecular Structure and Mechanisms (Pullman, A., Ed.) Kluwer, Amsterdam, The Netherlands.
    • (1995) Modeling of Biomolecular Structure and Mechanisms
    • Simmerling, C.1    Elber, R.2    Zhang, J.3
  • 30
    • 0024394912 scopus 로고
    • Prediction of DNA structure from sequence: A build-up technique
    • DOI 10.1002/bip.360280703
    • Hingerty, B. E., Figueroa, S., Hayden, T. L., and Broyde, S. (1989) Prediction of DNA structure from sequence: a build-up technique. Biopolymers 28, 1195-1222. (Pubitemid 19159066)
    • (1989) Biopolymers , vol.28 , Issue.7 , pp. 1195-1222
    • Hingerty, B.E.1    Figueroa, S.2    Hayden, T.L.3    Broyde, S.4
  • 31
    • 0024556774 scopus 로고
    • Conformational and helicoidal analysis of 30 ps of molecular dynamics on the d(CGCGAATTCGCG) double helix: "curves", dials and windows
    • Ravishanker, G., Swaminathan, S., Beveridge, D. L., Lavery, R., and Sklenar, H. (1989) Conformational and helicoidal analysis of 30 ps of molecular dynamics on the d(CGCGAATTCGCG) double helix: "curves", dials and windows. J. Biomol. Struct. Dyn. 6, 669-699.
    • (1989) J. Biomol. Struct. Dyn. , vol.6 , pp. 669-699
    • Ravishanker, G.1    Swaminathan, S.2    Beveridge, D.L.3    Lavery, R.4    Sklenar, H.5
  • 33
    • 0000066258 scopus 로고
    • Right-handed and left-handed DNA: Studies of B- and Z-DNA by using proton nuclear Overhauser effect and P NMR
    • Patel, D. J., Kozlowski, S. A., Nordheim, A., and Rich, A. (1982) Right-handed and left-handed DNA: studies of B- and Z-DNA by using proton nuclear Overhauser effect and P NMR. Proc. Natl. Acad. Sci. U.S.A. 79, 1413-1417.
    • (1982) Proc. Natl. Acad. Sci. U.S.A. , vol.79 , pp. 1413-1417
    • Patel, D.J.1    Kozlowski, S.A.2    Nordheim, A.3    Rich, A.4
  • 34
    • 0023386995 scopus 로고
    • DNA and RNA: NMR studies of conformations and dynamics in solution
    • Patel, D. J., Shapiro, L., and Hare, D. (1987) DNA and RNA: NMR studies of conformations and dynamics in solution. Q. Rev. Biophys. 20, 35-112.
    • (1987) Q. Rev. Biophys. , vol.20 , pp. 35-112
    • Patel, D.J.1    Shapiro, L.2    Hare, D.3
  • 35
    • 84988109709 scopus 로고
    • Nucleic-acids and nuclear magnetic-resonance
    • Vandeven, F. J. M., and Hilbers, C. W. (1988) Nucleic-acids and nuclear magnetic-resonance. Eur. J. Biochem. 178, 1-38.
    • (1988) Eur. J. Biochem. , vol.178 , pp. 1-38
    • Vandeven, F.J.M.1    Hilbers, C.W.2
  • 36
    • 0024381278 scopus 로고
    • 2-propanodeoxyguanosine adducts (X) opposite purines in DNA duplexes: Protonated X(syn)·A(anti) pairing (acidic pH) and X(syn)·G(anti) pairing (neutral pH) at the lesion site
    • Kouchakdjian, M., Marinelli, E., Gao, X. L., Johnson, F., Grollman, A., and Patel, D. (1989) NMR studies of exocyclic 1,N2-propanodeoxyguanosine adducts (X) opposite purines in DNA duplexes: protonated X(syn)·A(anti) pairing (acidic pH) and X(syn)·G(anti) pairing (neutral pH) at the lesion site. Biochemistry 28, 5647-5657. (Pubitemid 19175781)
    • (1989) Biochemistry , vol.28 , Issue.13 , pp. 5647-5657
    • Kouchakdjian, M.1    Marinelli, E.2    Gao, X.3    Johnson, F.4    Grollman, A.5    Patel, D.6
  • 37
    • 0025809945 scopus 로고
    • NMR studies of the exocyclic 1,N(6)-ethenodeoxyadenosine adduct (epsilon-dA) opposite deoxyguanosine in a DNA duplex: Epsilon-dA(syn) ·dG(anti) pairing at the lesion site
    • Santos, C. D., Kouchakdjian, M., Yarema, K., Basu, A., Essigmann, J., and Patel, D. J. (1991) NMR studies of the exocyclic 1,N(6)-ethenodeoxyadenosine adduct (epsilon-dA) opposite deoxyguanosine in a DNA duplex: epsilon-dA(syn)·dG(anti) pairing at the lesion site. Biochemistry 30, 1828-1835.
    • (1991) Biochemistry , vol.30 , pp. 1828-1835
    • Santos, C.D.1    Kouchakdjian, M.2    Yarema, K.3    Basu, A.4    Essigmann, J.5    Patel, D.J.6
  • 38
    • 0037633984 scopus 로고    scopus 로고
    • Mutagenic events induced by 4-hydroxyequilin in supF shuttle vector plasmid propagated in human cells
    • DOI 10.1093/carcin/bgg029
    • Yasui, M., Matsui, S., Laxmi, Y. R., Suzuki, N., Kim, S. Y., Shibutani, S., and Matsuda, T. (2003) Mutagenic events induced by 4-hydroxyequilin in supF shuttle vector plasmid propagated in human cells. Carcinogenesis 24, 911-917. (Pubitemid 36748908)
    • (2003) Carcinogenesis , vol.24 , Issue.5 , pp. 911-917
    • Yasui, M.1    Matsui, S.2    Santosh Laxmi, Y.R.3    Suzuki, N.4    Yeon Kim, S.5    Shibutani, S.6    Matsuda, T.7
  • 39
    • 34547557903 scopus 로고    scopus 로고
    • Mechanism of translesion synthesis past an equine estrogen-DNA adduct by Y-family DNA polymerases
    • Yasui, M., Suzuki, N., Liu, X., Okamoto, Y., Kim, S. Y., Laxmi, Y. R., and Shibutani, S. (2007) Mechanism of translesion synthesis past an equine estrogen-DNA adduct by Y-family DNA polymerases. J. Mol. Biol. 371, 1151-1162.
    • (2007) J. Mol. Biol. , vol.371 , pp. 1151-1162
    • Yasui, M.1    Suzuki, N.2    Liu, X.3    Okamoto, Y.4    Kim, S.Y.5    Laxmi, Y.R.6    Shibutani, S.7
  • 40
    • 0242396923 scopus 로고    scopus 로고
    • 3DNA: A software package for the analysis, rebuilding and visualization of three-dimensional nucleic acid structures
    • Lu, X. J., and Olson, W. K. (2003) 3DNA: a software package for the analysis, rebuilding and visualization of three-dimensional nucleic acid structures. Nucleic Acids Res. 31, 5108-5121.
    • (2003) Nucleic Acids Res. , vol.31 , pp. 5108-5121
    • Lu, X.J.1    Olson, W.K.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.