메뉴 건너뛰기




Volumn 41, Issue 13, 1998, Pages 2261-2267

Three-dimensional quantitative structure-activity relationship study of nonsteroidal estrogen receptor ligands using the comparative molecular field analysis/cross-validated r2-guided region selection approach

Author keywords

[No Author keywords available]

Indexed keywords

ESTRADIOL; ESTROGEN RECEPTOR;

EID: 15644363344     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9705521     Document Type: Article
Times cited : (60)

References (33)
  • 2
    • 15644361946 scopus 로고
    • Transcriptional activation by the estrogen receptor requires a conformational change in the ligand binding domain
    • Beekman, J. M.; Allan, G. F.; Tsai, S. Y.; Tsai, M.-J.; O'Malley, B. W. Transcriptional activation by the estrogen receptor requires a conformational change in the ligand binding domain. Mol. Endocrinol. 1993, 267, 19513-19520.
    • (1993) Mol. Endocrinol. , vol.267 , pp. 19513-19520
    • Beekman, J.M.1    Allan, G.F.2    Tsai, S.Y.3    Tsai, M.-J.4    O'Malley, B.W.5
  • 3
    • 0030071445 scopus 로고    scopus 로고
    • Tripartite steroid hormone receptor pharmacology: Interaction with multiple effector sites as a basis for the cell-and promoter-specific action of these hormones
    • Katzenellenbogen, J. A.; O'Malley, B. W.; Katzenellenbogen, B. S. Tripartite steroid hormone receptor pharmacology: interaction with multiple effector sites as a basis for the cell-and promoter-specific action of these hormones. Mol. Endocrinol. 1996, 10, 119-131.
    • (1996) Mol. Endocrinol. , vol.10 , pp. 119-131
    • Katzenellenbogen, J.A.1    O'Malley, B.W.2    Katzenellenbogen, B.S.3
  • 4
    • 3042833606 scopus 로고
    • Biochemical and estrogenic activity of some diethylstilbestrol metabolites and analogues in the mouse uterus
    • Leavitt, W., Ed.; Plenum: New York
    • Korach, K. S. Biochemical and estrogenic activity of some diethylstilbestrol metabolites and analogues in the mouse uterus. In Hormones and Cancer; Leavitt, W., Ed.; Plenum: New York, 1982; pp 39-62.
    • (1982) Hormones and Cancer , pp. 39-62
    • Korach, K.S.1
  • 5
    • 0024584317 scopus 로고
    • Diethylstilbestrol metabolites and analogues: Stereochemical probes for the estrogen receptor binding site
    • Korach, K. S.; Chae, K.; Levy, L. A.; Duax, W. L.; Sarvar, P. J. Diethylstilbestrol metabolites and analogues: stereochemical probes for the estrogen receptor binding site. J. Biol. Chem. 1989, 264, 5642-5647.
    • (1989) J. Biol. Chem. , vol.264 , pp. 5642-5647
    • Korach, K.S.1    Chae, K.2    Levy, L.A.3    Duax, W.L.4    Sarvar, P.J.5
  • 6
    • 0025789760 scopus 로고
    • Estrogen receptor stereo-chemistry: Ligand binding orientation and influence on biological activity
    • Chae, K.; Gibson, M.; Korach, K. S. Estrogen receptor stereo-chemistry: ligand binding orientation and influence on biological activity. Mol. Pharmacol. 1991, 40, 806-811.
    • (1991) Mol. Pharmacol. , vol.40 , pp. 806-811
    • Chae, K.1    Gibson, M.2    Korach, K.S.3
  • 7
    • 0021676156 scopus 로고
    • Molecular structures of metabolites and analogues of diethylstilbestrol and their relationship to receptor binding and biological activity
    • Duax, W. L.; Swenson, D. C.; Strong, P. D.; Korach, K. S.; McLachlan, J.; Metzler, M. Molecular structures of metabolites and analogues of diethylstilbestrol and their relationship to receptor binding and biological activity. Mol. Pharmacol. 1984, 26, 520-525.
    • (1984) Mol. Pharmacol. , vol.26 , pp. 520-525
    • Duax, W.L.1    Swenson, D.C.2    Strong, P.D.3    Korach, K.S.4    McLachlan, J.5    Metzler, M.6
  • 8
    • 0024424089 scopus 로고
    • 2-Arylindenes and 2-arylindenones: Molecular structures and considerations in the binding orientation of unsymmetrical nonsteroidal ligands to the estrogen receptor
    • Anstead, G. M.; Wilson, S. R.; Katzenellenbogen, J. A. 2-Arylindenes and 2-arylindenones: molecular structures and considerations in the binding orientation of unsymmetrical nonsteroidal ligands to the estrogen receptor. J. Med. Chem. 1989, 32, 2163-2171.
    • (1989) J. Med. Chem. , vol.32 , pp. 2163-2171
    • Anstead, G.M.1    Wilson, S.R.2    Katzenellenbogen, J.A.3
  • 9
    • 0023751431 scopus 로고
    • Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins
    • Gramer, R. D., III; Patterson, D. E.; Bunce, J. D. Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins. J. Am. Chem. Soc. 1988, 110, 5959-5967.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 5959-5967
    • Gramer III, R.D.1    Patterson, D.E.2    Bunce, J.D.3
  • 10
    • 0028063420 scopus 로고
    • Quantitative structure-activity relationships/comparative molecular field analysis (QSAR/ CoMFA) for receptor-binding properties of halogenated estradiol derivatives
    • Gantchev, T. G.; Ali, H.; van Lier, J. E. Quantitative structure-activity relationships/comparative molecular field analysis (QSAR/ CoMFA) for receptor-binding properties of halogenated estradiol derivatives. J. Med. Chem. 1994, 37, 4164-4176.
    • (1994) J. Med. Chem. , vol.37 , pp. 4164-4176
    • Gantchev, T.G.1    Ali, H.2    Van Lier, J.E.3
  • 11
    • 0029086592 scopus 로고
    • Using three-dimensional quantitative structure-activity relationships to examine estrogen receptor binding affinities of polychlorinated biphenyls
    • Waller, C.; Minor, D. L.; McKinney, J. D. Using three-dimensional quantitative structure-activity relationships to examine estrogen receptor binding affinities of polychlorinated biphenyls. Environ. Health Perspect. 1905, 103, 702-707.
    • (1905) Environ. Health Perspect. , vol.103 , pp. 702-707
    • Waller, C.1    Minor, D.L.2    McKinney, J.D.3
  • 13
    • 0029655006 scopus 로고
    • 2 guided region selection for comparative molecular field analysis (CoMFA): A simple method to achieve consistent results
    • 2 guided region selection for comparative molecular field analysis (CoMFA): a simple method to achieve consistent results. J. Med. Chem. 1995, 38, 1060-1066.
    • (1995) J. Med. Chem. , vol.38 , pp. 1060-1066
    • Cho, S.J.1    Tropsha, A.2
  • 14
    • 15644374290 scopus 로고    scopus 로고
    • Tripos inc., 1699 S. Hanley Rd., Suite 303, St. Louis, MO 63144
    • Tripos inc., 1699 S. Hanley Rd., Suite 303, St. Louis, MO 63144.
  • 15
    • 84988115618 scopus 로고
    • Validation of the general purpose Tripos 5.2 force field
    • Clark, M.; Cramer, R. D., III; Van Opdenbosch, N. Validation of the general purpose Tripos 5.2 force field. J. Comput. Chem. 1989, 10, 982-1012.
    • (1989) J. Comput. Chem. , vol.10 , pp. 982-1012
    • Clark, M.1    Cramer III, R.D.2    Van Opdenbosch, N.3
  • 16
    • 0018773081 scopus 로고
    • Estrogen action in the mouse uterus: Characterization of cytosol and nuclear receptor systems
    • Korach, K. S. Estrogen action in the mouse uterus: characterization of cytosol and nuclear receptor systems. Endocrinology 1979, 104, 1324-1332.
    • (1979) Endocrinology , vol.104 , pp. 1324-1332
    • Korach, K.S.1
  • 17
    • 0002218591 scopus 로고
    • The structure of the crystalline complex estradiol urea (1:1)
    • Duax, W. L. The structure of the crystalline complex estradiol urea (1:1). Acta Crystallogr. 1972, B28, 1864-1871.
    • (1972) Acta Crystallogr. , vol.B28 , pp. 1864-1871
    • Duax, W.L.1
  • 18
    • 0041195441 scopus 로고
    • Etude cristallographique de differentes formes solvatees du diethylstilboestrol. (Crystal-lographic study of different solvated forms of diethylstilbestrol.)
    • Busetta, P. B.; Hospital, C. C. Etude cristallographique de differentes formes solvatees du diethylstilboestrol. (Crystal-lographic study of different solvated forms of diethylstilbestrol.) Acta Crystallogr. 1973, B29, 2456-2462.
    • (1973) Acta Crystallogr. , vol.B29 , pp. 2456-2462
    • Busetta, P.B.1    Hospital, C.C.2
  • 20
    • 84886623078 scopus 로고
    • A series of optical structural and isomeric analogues of estradiol: A comparative study of the biological activity and affinity to cytosol receptor of rabbit uterus
    • Chernyaev, G. A.; Barkova, T. I; Egorova, V.; Sorokina, I. B.; Anachenko, S. N.; Matarodze, G. D.; Sokolova, N. A.; Rozen, V. B. A series of optical structural and isomeric analogues of estradiol: a comparative study of the biological activity and affinity to cytosol receptor of rabbit uterus. J. Steroid Biochem. 1975, 6, 1483-1488.
    • (1975) J. Steroid Biochem. , vol.6 , pp. 1483-1488
    • Chernyaev, G.A.1    Barkova, T.I.2    Egorova, V.3    Sorokina, I.B.4    Anachenko, S.N.5    Matarodze, G.D.6    Sokolova, N.A.7    Rozen, V.B.8
  • 21
    • 0003146242 scopus 로고
    • Molecular basis of estrogenicity: X-ray crystallographic studies
    • McLachlan, J., Ed.; Elsevier/North-Holland: New York
    • Duax, W. L.; Weeks, C. M. Molecular basis of estrogenicity: X-ray crystallographic studies. In Estrogens in the Environment; McLachlan, J., Ed.; Elsevier/North-Holland: New York, 1980; pp 111-131.
    • (1980) Estrogens in the Environment , pp. 111-131
    • Duax, W.L.1    Weeks, C.M.2
  • 23
    • 0000261607 scopus 로고    scopus 로고
    • Structure-based alignment and comparative molecular field analysis of acetyl-cholinesterase inhibitors
    • Cho, S. J.; Garsia, M. L. S.; Bier, J.; Tropsha, A. Structure-based alignment and comparative molecular field analysis of acetyl-cholinesterase inhibitors. J. Med. Chem. 1996, 39, 5064-5071.
    • (1996) J. Med. Chem. , vol.39 , pp. 5064-5071
    • Cho, S.J.1    Garsia, M.L.S.2    Bier, J.3    Tropsha, A.4
  • 24
    • 0025896525 scopus 로고
    • Estrogen receptor stereochemistry: Ligand binding and hormonal responsiveness
    • Korach, K. S.; Chae, K.; Gibson, M.; Curtis, S. Estrogen receptor stereochemistry: ligand binding and hormonal responsiveness. Steroids 1991, 56, 263-270.
    • (1991) Steroids , vol.56 , pp. 263-270
    • Korach, K.S.1    Chae, K.2    Gibson, M.3    Curtis, S.4
  • 25
    • 0029030873 scopus 로고
    • 11-Beta substituted estradiol derivatives - Potential high-affinity carbon-11-labeled probes for the estrogen receptor: A structure-activity-relationship
    • Napolitano, E.; Fiaschi, R.; Carlson, K. E.; Katzenellenbogen, J. A. 11-Beta substituted estradiol derivatives - potential high-affinity carbon-11-labeled probes for the estrogen receptor: a structure-activity-relationship. J. Med. Chem. 1995, 38, 429-434.
    • (1995) J. Med. Chem. , vol.38 , pp. 429-434
    • Napolitano, E.1    Fiaschi, R.2    Carlson, K.E.3    Katzenellenbogen, J.A.4
  • 26
    • 0019834788 scopus 로고
    • Drug interaction with estrogen receptors for the control of breast neoplasia (review.)
    • Leclercq, G.; Heuson, J. C. Drug interaction with estrogen receptors for the control of breast neoplasia (review.). Anticancer Res. 1981, 1, 217-228.
    • (1981) Anticancer Res. , vol.1 , pp. 217-228
    • Leclercq, G.1    Heuson, J.C.2
  • 27
    • 0028943868 scopus 로고
    • Molecular modeling studies on 11β-aminoethoxyphenyl and 7α-aminoethoxyphenyl estradiols. evidence suggesting a common hydrophobic pocket in estrogen receptor
    • Poupaert, J. H.; Lambert, D. M.; Vamecq, J.; Abul-Hajj, Y. J. Molecular modeling studies on 11β-aminoethoxyphenyl and 7α-aminoethoxyphenyl estradiols. evidence suggesting a common hydrophobic pocket in estrogen receptor. Bioorg. Med. Chem. Lett. 1995, 5, 839-842.
    • (1995) Bioorg. Med. Chem. Lett. , vol.5 , pp. 839-842
    • Poupaert, J.H.1    Lambert, D.M.2    Vamecq, J.3    Abul-Hajj, Y.J.4
  • 28
    • 0019725582 scopus 로고
    • Molecular details of receptor binding and hormonal action of steroids derived from X-ray crystallographic investigations
    • Duax, W. L.; Griffin, J. F.; Rohrer, D. C.; Swenson, D. C.; Weeks, C. M. Molecular details of receptor binding and hormonal action of steroids derived from X-ray crystallographic investigations. J. Steroid Biochem. 1981, 15, 41-47.
    • (1981) J. Steroid Biochem. , vol.15 , pp. 41-47
    • Duax, W.L.1    Griffin, J.F.2    Rohrer, D.C.3    Swenson, D.C.4    Weeks, C.M.5
  • 29
    • 0030571293 scopus 로고    scopus 로고
    • D-ring alkylamide derivatives of estradiol: Effect on ER-binding affinity and antiestrogenic activity
    • Poirier, D.; Merand, Y.; Labrie, C.; Labrie, F. D-ring alkylamide derivatives of estradiol: effect on ER-binding affinity and antiestrogenic activity. Bioorg. Med. Chem. Lett. 1996, 6, 2537-2542.
    • (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 2537-2542
    • Poirier, D.1    Merand, Y.2    Labrie, C.3    Labrie, F.4
  • 31
    • 0023689751 scopus 로고
    • The mechanism of action of steroid antagonists: Insights from crystallographic studies
    • Duax, W. L.; Griffen, J. F.; Weeks, C. M.; Wawrzak, Z. The mechanism of action of steroid antagonists: insights from crystallographic studies. J. Steroid Biochem. 1988, 31, 481-492.
    • (1988) J. Steroid Biochem. , vol.31 , pp. 481-492
    • Duax, W.L.1    Griffen, J.F.2    Weeks, C.M.3    Wawrzak, Z.4
  • 32
    • 0023839436 scopus 로고
    • Estrogen receptor binding activity of polychlorinated hydroxy-biphenyls: Conformationally restricted structural probes
    • Korach, K. S.; Sarver, P.; Chae, K.; McLachlan, J. A.; McKinney, J. Estrogen receptor binding activity of polychlorinated hydroxy-biphenyls: conformationally restricted structural probes. Mol. Pharmacol. 1987, 33, 120-126.
    • (1987) Mol. Pharmacol. , vol.33 , pp. 120-126
    • Korach, K.S.1    Sarver, P.2    Chae, K.3    McLachlan, J.A.4    McKinney, J.5
  • 33
    • 0004819203 scopus 로고
    • Estrogenic activity in vivo and in vitro of some diethylstilbestrol metabolites and analogues
    • Korach, K. S.; Metzler, M.; McLachlan, J. A. Estrogenic activity in vivo and in vitro of some diethylstilbestrol metabolites and analogues. Proc. Natl. Acad. Sci. U.S.A. 1978, 75, 468-471.
    • (1978) Proc. Natl. Acad. Sci. U.S.A. , vol.75 , pp. 468-471
    • Korach, K.S.1    Metzler, M.2    McLachlan, J.A.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.