메뉴 건너뛰기




Volumn 52, Issue 3, 2009, Pages 858-867

Structural evolutions of salicylaldoximes as selective agonists for estrogen receptor β

Author keywords

[No Author keywords available]

Indexed keywords

ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; FLUORINE; PHENYL GROUP; SALICYLALDOXIME; SELECTIVE ESTROGEN RECEPTOR MODULATOR; LIGAND; OXIME;

EID: 61449153994     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm801458t     Document Type: Article
Times cited : (39)

References (36)
  • 4
    • 33748346434 scopus 로고    scopus 로고
    • Estrogen receptor (ER)-β isoforms: A key to understanding ER-β signalling
    • Leung, Y.-K.; Mak, P.; Hassan, S.; Ho, S.-M. Estrogen receptor (ER)-β isoforms: A key to understanding ER-β signalling. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 13162-13167.
    • (2006) Proc. Natl. Acad. Sci. U.S.A , vol.103 , pp. 13162-13167
    • Leung, Y.-K.1    Mak, P.2    Hassan, S.3    Ho, S.-M.4
  • 5
    • 0033305454 scopus 로고    scopus 로고
    • Selective estrogen receptor modulators: Clinical spectrum
    • Cosman, F.; Lindsay, R. Selective estrogen receptor modulators: clinical spectrum. Endocr. Rev. 1999, 20, 418-434.
    • (1999) Endocr. Rev , vol.20 , pp. 418-434
    • Cosman, F.1    Lindsay, R.2
  • 6
    • 33845904405 scopus 로고    scopus 로고
    • Chemoprevention of breast cancer with selective oestrogen-receptor modulators
    • Jordan, V. C. Chemoprevention of breast cancer with selective oestrogen-receptor modulators. Nat Rev Cancer 2007, 7, 46-53.
    • (2007) Nat Rev Cancer , vol.7 , pp. 46-53
    • Jordan, V.C.1
  • 8
    • 3042840787 scopus 로고    scopus 로고
    • Dissecting physiological roles of estrogen receptor a and β with potent selective ligands from structure-based design
    • In this case, the effect due to ERβ-stimulation appears to be inferior with respect to ERa-agonists, see
    • In this case, the effect due to ERβ-stimulation appears to be inferior with respect to ERa-agonists, see Hillisch, A.; Peters, O.; Kosemund, D.; Muller, G.; Walter, A.; Schneider, B.; Reddersen, G.; Elger, W.; Fritzemeier, K.-H. Dissecting physiological roles of estrogen receptor a and β with potent selective ligands from structure-based design. Mol. Endocrinol. 2004, 18, 1599-1609.
    • (2004) Mol. Endocrinol , vol.18 , pp. 1599-1609
    • Hillisch, A.1    Peters, O.2    Kosemund, D.3    Muller, G.4    Walter, A.5    Schneider, B.6    Reddersen, G.7    Elger, W.8    Fritzemeier, K.-H.9
  • 11
  • 14
    • 0035923672 scopus 로고    scopus 로고
    • There are several examples of successful bioisosteric replacements in the field of nuclear receptors; for example, three carbon atoms constituting the o-aminophenone group of farglitazar, a PPARa agonist, were removed, leading to a vinylogous amide analogue retaining activity. Xu, H. E, Lambert, M. H, Montana, V. G, Plunket, K. D, Moore, L. B, Collins, J. L, Oplinger, J. A, Kliewer, S. A, Gampe, R. T, Jr, McKee, D. D, Moore, J. T, Willson, T. M. Structural determinants of ligand binding selectivity between the peroxisome proliferators-activated receptors. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 13919-13924
    • There are several examples of successful bioisosteric replacements in the field of nuclear receptors; for example, three carbon atoms constituting the o-aminophenone group of farglitazar, a PPARa agonist, were removed, leading to a vinylogous amide analogue retaining activity. Xu, H. E.; Lambert, M. H.; Montana, V. G.; Plunket, K. D.; Moore, L. B.; Collins, J. L.; Oplinger, J. A.; Kliewer, S. A.; Gampe, R. T., Jr.; McKee, D. D.; Moore, J. T.; Willson, T. M. Structural determinants of ligand binding selectivity between the peroxisome proliferators-activated receptors. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 13919-13924.
  • 17
    • 23044493455 scopus 로고    scopus 로고
    • ANew and Efficient Synthesis of 4-Functionalized Benzo[b]furans from 2,3-Dihalophenols
    • Sanz, R.; Castroviejo, M. P.; Fernández, Y.; Fañanás, F.J.ANew and Efficient Synthesis of 4-Functionalized Benzo[b]furans from 2,3-Dihalophenols. J. Org. Chem. 2005, 70, 6548-6551.
    • (2005) J. Org. Chem , vol.70 , pp. 6548-6551
    • Sanz, R.1    Castroviejo, M.P.2    Fernández, Y.3    Fañanás, F.J.4
  • 18
    • 0001039272 scopus 로고
    • Structural Studies by Nuclear Magnetic Resonance. XI: Conformations and Configurations of Oxime O-Methyl Ethers
    • Karabatsos, G. J.; Hsi, N. Structural Studies by Nuclear Magnetic Resonance. XI: Conformations and Configurations of Oxime O-Methyl Ethers. Tetrahedron 1967, 23, 1079-1095.
    • (1967) Tetrahedron , vol.23 , pp. 1079-1095
    • Karabatsos, G.J.1    Hsi, N.2
  • 20
    • 0015902629 scopus 로고
    • Photoaffinity Labels for Estrogen Binding Proteins of Rat Uterus
    • Katzenellenbogen, J. A.; Johnson, H. J., Jr.; Myers, H. N. Photoaffinity Labels for Estrogen Binding Proteins of Rat Uterus. Biochemistry 1973, 12, 4085-4092.
    • (1973) Biochemistry , vol.12 , pp. 4085-4092
    • Katzenellenbogen, J.A.1    Johnson Jr., H.J.2    Myers, H.N.3
  • 21
    • 0030734795 scopus 로고    scopus 로고
    • Altered Ligand Binding Properties and Enhanced Stability of a Constitutively Active Estrogen Receptor: Evidence That an Open-Pocket Conformation is Required for Ligand Interaction
    • Carlson, K. E.; Choi, I.; Gee, A.; Katzenellenbogen, B. S.; Katzenel-lenbogen, J. A. Altered Ligand Binding Properties and Enhanced Stability of a Constitutively Active Estrogen Receptor: Evidence That an Open-Pocket Conformation is Required for Ligand Interaction. Biochemistry 1997, 36, 14897-14905.
    • (1997) Biochemistry , vol.36 , pp. 14897-14905
    • Carlson, K.E.1    Choi, I.2    Gee, A.3    Katzenellenbogen, B.S.4    Katzenel-lenbogen, J.A.5
  • 24
    • 33846665564 scopus 로고    scopus 로고
    • ERβ ligands. Part 5: Synthesis and structure-activity relationships of a series of 4'-hydroxyphenyl-aryl-carbaldehyde oxime derivatives
    • and references therein
    • (c)Mewshaw, R. E.; Bowen, S. M.; Harris, H. A.; Xu, Z. B.; Manas, E. S.; Cohn, S. T. ERβ ligands. Part 5: Synthesis and structure-activity relationships of a series of 4'-hydroxyphenyl-aryl-carbaldehyde oxime derivatives. Bioorg. Med. Chem. Lett. 2007, 17, 902-906, and references therein.
    • (2007) Bioorg. Med. Chem. Lett , vol.17 , pp. 902-906
    • Mewshaw, R.E.1    Bowen, S.M.2    Harris, H.A.3    Xu, Z.B.4    Manas, E.S.5    Cohn, S.T.6
  • 25
    • 0004752110 scopus 로고    scopus 로고
    • Novel ligands that function as selective estrogens or antiestrogens for estrogen receptor-a or estrogen receptorβ
    • Sun, J.; Meyers, M. J.; Fink, B. E.; Rajendran, R.; Katzenellenbogen, J. A.; Katzenellenbogen, B. S. Novel ligands that function as selective estrogens or antiestrogens for estrogen receptor-a or estrogen receptorβ. Endocrinology 1999, 140, 800-804.
    • (1999) Endocrinology , vol.140 , pp. 800-804
    • Sun, J.1    Meyers, M.J.2    Fink, B.E.3    Rajendran, R.4    Katzenellenbogen, J.A.5    Katzenellenbogen, B.S.6
  • 27
    • 0027424372 scopus 로고
    • Structure-function analysis of the hormone binding domain of the human estrogen receptor by region-specific mutagenesis and phenotypic screening in yeast
    • Wrenn, C. K.; Katzenellenbogen, B. S. Structure-function analysis of the hormone binding domain of the human estrogen receptor by region-specific mutagenesis and phenotypic screening in yeast. J. Biol. Chem. 1993, 268, 24089-24098.
    • (1993) J. Biol. Chem , vol.268 , pp. 24089-24098
    • Wrenn, C.K.1    Katzenellenbogen, B.S.2
  • 28
    • 0031789876 scopus 로고    scopus 로고
    • Transcription activation by the human estrogen receptor subtype β (ERβ) studied with ERβ and ERα receptor chimeras
    • McInerney, E. M.; Weis, K. E.; Sun, J.; Mosselman, S.; Katzenel-lenbogen, B. S. Transcription activation by the human estrogen receptor subtype β (ERβ) studied with ERβ and ERα receptor chimeras. Endocrinology 1998, 139, 4513-4522.
    • (1998) Endocrinology , vol.139 , pp. 4513-4522
    • McInerney, E.M.1    Weis, K.E.2    Sun, J.3    Mosselman, S.4    Katzenel-lenbogen, B.S.5
  • 32
    • 64549111047 scopus 로고    scopus 로고
    • Maestro, version 7.5; Schrodinger Inc, Portland, OR, 1999
    • Maestro, version 7.5; Schrodinger Inc.: Portland, OR, 1999.
  • 33
    • 64549142531 scopus 로고    scopus 로고
    • Macromodel, version 8.5; Schrodinger Inc, Portland, OR, 1999
    • Macromodel, version 8.5; Schrodinger Inc.: Portland, OR, 1999.
  • 34
    • 11644261806 scopus 로고    scopus 로고
    • Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function
    • Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belew, R. K.; Olson, A. J. Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. J. Comput. Chem. 1998, 19, 1639-1662.
    • (1998) J. Comput. Chem , vol.19 , pp. 1639-1662
    • Morris, G.M.1    Goodsell, D.S.2    Halliday, R.S.3    Huey, R.4    Hart, W.E.5    Belew, R.K.6    Olson, A.J.7
  • 35
    • 0033397980 scopus 로고    scopus 로고
    • Sanner, M. F. Python: A Programming Language for Software Integration and Development. J. Mol. Graphics Modell. 1999, 17, 57-61.
    • Sanner, M. F. Python: A Programming Language for Software Integration and Development. J. Mol. Graphics Modell. 1999, 17, 57-61.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.