메뉴 건너뛰기




Volumn 48, Issue 9, 2008, Pages 1882-1890

Computationally identified novel diphenyl- and phenylpyridine androgen receptor antagonist structures

Author keywords

[No Author keywords available]

Indexed keywords

3D MODELING; CELL PROLIFERATION; CELLS; COMPUTATIONAL CHEMISTRY; DISEASES; MOLECULAR GRAPHICS; UROLOGY;

EID: 54249141064     PISSN: 15499596     EISSN: 1549960X     Source Type: Journal    
DOI: 10.1021/ci800149w     Document Type: Article
Times cited : (14)

References (45)
  • 1
    • 33746894825 scopus 로고    scopus 로고
    • Pharmacokinetics and pharmacodynamics of nonsteroidal androgen receptor ligands
    • Gao, W.; Kim, J.; Dalton, J. T. Pharmacokinetics and pharmacodynamics of nonsteroidal androgen receptor ligands. Pharm. Res. 2006, 23, 1641-1658.
    • (2006) Pharm. Res , vol.23 , pp. 1641-1658
    • Gao, W.1    Kim, J.2    Dalton, J.T.3
  • 3
    • 2642544224 scopus 로고    scopus 로고
    • The androgen receptor gene mutations database (ARDB): 2004 update
    • Gottlieb, B.; Beitel, L. K.; Wu, J. H.; Trifiro, M. The androgen receptor gene mutations database (ARDB): 2004 update. Hum. Mutat. 2004, 23, 527-533.
    • (2004) Hum. Mutat , vol.23 , pp. 527-533
    • Gottlieb, B.1    Beitel, L.K.2    Wu, J.H.3    Trifiro, M.4
  • 4
    • 17844376217 scopus 로고    scopus 로고
    • Structural basis for antagonism and resistance of bicalutamide in prostate cancer
    • Bohl, C. E.; Gao, W.; Miller, D. D.; Bell, C. E.; Dalton, J. T. Structural basis for antagonism and resistance of bicalutamide in prostate cancer. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 6201-6206.
    • (2005) Proc. Natl. Acad. Sci. U.S.A , vol.102 , pp. 6201-6206
    • Bohl, C.E.1    Gao, W.2    Miller, D.D.3    Bell, C.E.4    Dalton, J.T.5
  • 5
    • 27844611242 scopus 로고    scopus 로고
    • Structural basis for accommodation of nonsteroidal ligands in the androgen receptor
    • Bohl, C. E.; Miller, D. D.; Chen, J.; Bell, C. E.; Dalton, J. T. Structural basis for accommodation of nonsteroidal ligands in the androgen receptor. J. Biol. Chem. 2005, 280, 37747-37754.
    • (2005) J. Biol. Chem , vol.280 , pp. 37747-37754
    • Bohl, C.E.1    Miller, D.D.2    Chen, J.3    Bell, C.E.4    Dalton, J.T.5
  • 6
    • 34250365377 scopus 로고    scopus 로고
    • Crystal structure of the T877A human androgen receptor ligand-binding domain complexed to cyproterone acetate provides insight for ligandinduced conformational changes and structure-based drug design
    • Bohl, C. E.; Wu, Z.; Miller, D. D.; Bell, C. E.; Dalton, J. T. Crystal structure of the T877A human androgen receptor ligand-binding domain complexed to cyproterone acetate provides insight for ligandinduced conformational changes and structure-based drug design. J. Biol. Chem. 2007, 282, 13648-13655.
    • (2007) J. Biol. Chem , vol.282 , pp. 13648-13655
    • Bohl, C.E.1    Wu, Z.2    Miller, D.D.3    Bell, C.E.4    Dalton, J.T.5
  • 8
    • 35648970526 scopus 로고    scopus 로고
    • Structural characterization of the human androgen receptor ligand-binding domain complexed with EM5744, a rationally designed steroidal ligand bearing a bulky chain directed toward helix 12
    • Cantin, L.; Faucher, F.; Couture, J. F.; de Jesus-Tran, K. P.; Legrand, P.; Ciobanu, L. C.; Frechette, Y.; Labrecque, R.; Singh, S. M.; Labrie, F.; Breton, R. Structural characterization of the human androgen receptor ligand-binding domain complexed with EM5744, a rationally designed steroidal ligand bearing a bulky chain directed toward helix 12. J. Biol. Chem. 2007, 282, 30910-30919.
    • (2007) J. Biol. Chem , vol.282 , pp. 30910-30919
    • Cantin, L.1    Faucher, F.2    Couture, J.F.3    de Jesus-Tran, K.P.4    Legrand, P.5    Ciobanu, L.C.6    Frechette, Y.7    Labrecque, R.8    Singh, S.M.9    Labrie, F.10    Breton, R.11
  • 10
    • 13944264638 scopus 로고    scopus 로고
    • Three-dimensional structure-activity relationships of nonsteroidal ligands in complex with androgen receptor ligand-binding domain
    • Söderholm, A. A.; Lehtovuori, P. T.; Nyrönen, T. H. Three-dimensional structure-activity relationships of nonsteroidal ligands in complex with androgen receptor ligand-binding domain. J. Med. Chem. 2005, 48, 917-925.
    • (2005) J. Med. Chem , vol.48 , pp. 917-925
    • Söderholm, A.A.1    Lehtovuori, P.T.2    Nyrönen, T.H.3
  • 11
    • 0023751431 scopus 로고
    • Comparative molecular field analysis (CoMFA) 1. Effect of shape on binding of steroids to carrier proteins
    • Cramer III R. D.; 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
    • Cramer III, R.D.1    Patterson, D.E.2    Bunce, J.D.3
  • 12
    • 0027944195 scopus 로고
    • Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity
    • Klebe, G.; Abraham, U.; Mietzner, T. Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity. J. Med. Chem. 1994, 37, 4130-4146.
    • (1994) J. Med. Chem , vol.37 , pp. 4130-4146
    • Klebe, G.1    Abraham, U.2    Mietzner, T.3
  • 13
    • 0031552362 scopus 로고    scopus 로고
    • Development and validation of a genetic algorithm for flexible docking
    • Jones, G.; Willett, P.; Glen, R. C.; Leach, A. R.; Taylor, R. Development and validation of a genetic algorithm for flexible docking. J. Mol. Biol. 1997, 267, 727-748.
    • (1997) J. Mol. Biol , vol.267 , pp. 727-748
    • Jones, G.1    Willett, P.2    Glen, R.C.3    Leach, A.R.4    Taylor, R.5
  • 14
    • 2942683344 scopus 로고    scopus 로고
    • The highly conserved region of the corepressor Sin3A functionally interacts with the co-repressor Alien
    • Moehren, U.; Dressel, U.; Reeb, C. A.; Vaisanen, S.; Dunlop, T. W.; Carlberg, C.; Baniahmad, A. The highly conserved region of the corepressor Sin3A functionally interacts with the co-repressor Alien. Nucleic Acids Res. 2004, 32, 2995-3004.
    • (2004) Nucleic Acids Res , vol.32 , pp. 2995-3004
    • Moehren, U.1    Dressel, U.2    Reeb, C.A.3    Vaisanen, S.4    Dunlop, T.W.5    Carlberg, C.6    Baniahmad, A.7
  • 15
    • 0036635757 scopus 로고    scopus 로고
    • Human cell lines engineered for tetracycline-regulated expression of tumor suppressor candidate genes from a frequently affected chromosomal region, 3p21
    • Protopopov, A. I.; Li, J.; Winberg, G.; Gizatullin, R. Z.; Kashuba, V. I.; Klein, G.; Zabarovsky, E. R. Human cell lines engineered for tetracycline-regulated expression of tumor suppressor candidate genes from a frequently affected chromosomal region, 3p21. J. Gene Med. 2002, 4, 397-406.
    • (2002) J. Gene Med , vol.4 , pp. 397-406
    • Protopopov, A.I.1    Li, J.2    Winberg, G.3    Gizatullin, R.Z.4    Kashuba, V.I.5    Klein, G.6    Zabarovsky, E.R.7
  • 17
    • 54249145001 scopus 로고    scopus 로고
    • Maestro, version 8.0; Schrödinger, LLC: New York, 2007
    • Maestro, version 8.0; Schrödinger, LLC: New York, 2007.
  • 18
    • 54249098546 scopus 로고    scopus 로고
    • Prime, version 1.6; Schrödinger, LLC: New York, 2007
    • Prime, version 1.6; Schrödinger, LLC: New York, 2007.
  • 19
    • 0000490166 scopus 로고
    • From atoms and bonds to three-dimensional atomic coordinates: Model builders
    • Sadowski, J.; Gasteiger, J. From atoms and bonds to three-dimensional atomic coordinates: model builders. Chem. Rev. 1993, 93, 2567-2581.
    • (1993) Chem. Rev , vol.93 , pp. 2567-2581
    • Sadowski, J.1    Gasteiger, J.2
  • 20
    • 0028466540 scopus 로고
    • Comparison of automatic threedimensional model builders using 639 x-ray structures
    • Sadowski, J.; Gasteiger, J.; Klebe, G. Comparison of automatic threedimensional model builders using 639 x-ray structures. J. Chem. Inf. Comput. Sci. 1994, 34, 1000-1008.
    • (1994) J. Chem. Inf. Comput. Sci , vol.34 , pp. 1000-1008
    • Sadowski, J.1    Gasteiger, J.2    Klebe, G.3
  • 21
    • 54249112681 scopus 로고    scopus 로고
    • Impact, version 4.5; Schrödinger, LLC: New York, 2005
    • Impact, version 4.5; Schrödinger, LLC: New York, 2005.
  • 22
    • 54249132439 scopus 로고    scopus 로고
    • Schrödinger Suite 2007 Induced Fit Docking protocol. Glide, version 4.5; Schrödinger, LLC: New York, 2005;
    • Schrödinger Suite 2007 Induced Fit Docking protocol. Glide, version 4.5; Schrödinger, LLC: New York, 2005;
  • 23
    • 54249113573 scopus 로고    scopus 로고
    • Prime, version 1.6; Schrö dinger, LLC: New York, 2005
    • Prime, version 1.6; Schrö dinger, LLC: New York, 2005.
  • 24
    • 31544450787 scopus 로고    scopus 로고
    • Novel procedure for modeling ligand/receptor induced fit effects
    • Sherman, W.; Day, T.; Jacobson, M. P.; Friesner, R. A.; Farid, R. Novel procedure for modeling ligand/receptor induced fit effects. J. Med. Chem. 2006, 49, 534-553.
    • (2006) J. Med. Chem , vol.49 , pp. 534-553
    • Sherman, W.1    Day, T.2    Jacobson, M.P.3    Friesner, R.A.4    Farid, R.5
  • 25
    • 10044294023 scopus 로고    scopus 로고
    • An extensive test of 14 scoring functions using the PDBbind refined set of 800 protein-ligand complexes
    • Wang, R.; Lu, Y.; Fang, X.; Wang, S. An extensive test of 14 scoring functions using the PDBbind refined set of 800 protein-ligand complexes. J. Chem. Inf. Comput. Sci. 2004, 44, 2114-2125.
    • (2004) J. Chem. Inf. Comput. Sci , vol.44 , pp. 2114-2125
    • Wang, R.1    Lu, Y.2    Fang, X.3    Wang, S.4
  • 26
    • 0037763817 scopus 로고    scopus 로고
    • Comparative evaluation of 11 scoring functions for molecular docking
    • Wang, R.; Lu, Y.; Wang, S. Comparative evaluation of 11 scoring functions for molecular docking. J. Med. Chem. 2003, 46, 2287-2303.
    • (2003) J. Med. Chem , vol.46 , pp. 2287-2303
    • Wang, R.1    Lu, Y.2    Wang, S.3
  • 28
    • 34250800192 scopus 로고    scopus 로고
    • Alien interacts with the human androgen receptor and inhibits prostate cancer cell growth
    • Moehren, U.; Papaioannou, M.; Reeb, C. A.; Hong, W.; Baniahmad, A. Alien interacts with the human androgen receptor and inhibits prostate cancer cell growth. Mol. Endocrinol. 2007, 21, 1039-1048.
    • (2007) Mol. Endocrinol , vol.21 , pp. 1039-1048
    • Moehren, U.1    Papaioannou, M.2    Reeb, C.A.3    Hong, W.4    Baniahmad, A.5
  • 29
    • 0033152164 scopus 로고    scopus 로고
    • Selection for androgen receptor mutations in prostate cancers treated with androgen antagonist
    • Taplin, M. E.; Bubley, G. J.; Ko, Y. J.; Small, E. J.; Upton, M.; Rajeshkumar, B.; Balk, S. P. Selection for androgen receptor mutations in prostate cancers treated with androgen antagonist. Cancer Res. 1999, 59, 2511-2515.
    • (1999) Cancer Res , vol.59 , pp. 2511-2515
    • Taplin, M.E.1    Bubley, G.J.2    Ko, Y.J.3    Small, E.J.4    Upton, M.5    Rajeshkumar, B.6    Balk, S.P.7
  • 31
    • 0026591729 scopus 로고
    • Anti-androgens and the mutated androgen receptor of LNCaP cells: Differential effects on binding affinity, heat-shock protein interaction, and transcription activation
    • Veldscholte, J.; Berrevoets, C. A.; Brinkmann, A. O.; Grootegoed, J. A.; Mulder, E. Anti-androgens and the mutated androgen receptor of LNCaP cells: differential effects on binding affinity, heat-shock protein interaction, and transcription activation. Biochemistry 1992, 31, 2393-2399.
    • (1992) Biochemistry , vol.31 , pp. 2393-2399
    • Veldscholte, J.1    Berrevoets, C.A.2    Brinkmann, A.O.3    Grootegoed, J.A.4    Mulder, E.5
  • 32
    • 25444496757 scopus 로고    scopus 로고
    • Chemistry and structural biology of androgen receptor
    • Gao, W.; Bohl, C. E.; Dalton, J. T. Chemistry and structural biology of androgen receptor. Chem. Rev. 2005, 105, 3352-3370.
    • (2005) Chem. Rev , vol.105 , pp. 3352-3370
    • Gao, W.1    Bohl, C.E.2    Dalton, J.T.3
  • 33
    • 0037226103 scopus 로고    scopus 로고
    • Novel mutations of androgen receptor: A possible mechanism of bicalutamide withdrawal syndrome
    • Hara, T.; Miyazaki, J.; Araki, H.; Yamaoka, M.; Kanzaki, N.; Kusaka, M.; Miyamoto, M. Novel mutations of androgen receptor: a possible mechanism of bicalutamide withdrawal syndrome. Cancer Res. 2003, 63, 149-153.
    • (2003) Cancer Res , vol.63 , pp. 149-153
    • Hara, T.1    Miyazaki, J.2    Araki, H.3    Yamaoka, M.4    Kanzaki, N.5    Kusaka, M.6    Miyamoto, M.7
  • 34
    • 0034306499 scopus 로고    scopus 로고
    • Nuclear receptor ligandbinding domains: Three-dimensional structures, molecular interactions and pharmacological implications
    • Bourguet, W.; Germain, P.; Gronemeyer, H. Nuclear receptor ligandbinding domains: three-dimensional structures, molecular interactions and pharmacological implications. Trends Pharmacol. Sci. 2000, 21, 381-388.
    • (2000) Trends Pharmacol. Sci , vol.21 , pp. 381-388
    • Bourguet, W.1    Germain, P.2    Gronemeyer, H.3
  • 35
    • 3242784885 scopus 로고    scopus 로고
    • Mechanism of the nuclear receptor molecular switch
    • Nagy, L.; Schwabe, J. W. Mechanism of the nuclear receptor molecular switch. Trends Biochem. Sci. 2004, 29, 317-324.
    • (2004) Trends Biochem. Sci , vol.29 , pp. 317-324
    • Nagy, L.1    Schwabe, J.W.2
  • 37
    • 0032446607 scopus 로고    scopus 로고
    • The structural basis of estrogen receptor/coactivator recognition and me antagonism of this interaction by tamoxifen
    • Shiau, A. K.; Barstad, D.; Loria, P. M.; Cheng, L.; Kushner, P. J.; Agard, D. A.; Greene, G. L. The structural basis of estrogen receptor/coactivator recognition and me antagonism of this interaction by tamoxifen. Cell 1998, 95, 927-937.
    • (1998) Cell , vol.95 , pp. 927-937
    • Shiau, A.K.1    Barstad, D.2    Loria, P.M.3    Cheng, L.4    Kushner, P.J.5    Agard, D.A.6    Greene, G.L.7
  • 38
    • 0030986236 scopus 로고    scopus 로고
    • A signature motif in transcriptional co-activators mediates binding to nuclear receptors
    • Heery, D. M.; Kalkhoven, E.; Hoare, S.; Parker, M. G. A signature motif in transcriptional co-activators mediates binding to nuclear receptors. Nature 1997, 387, 733-736.
    • (1997) Nature , vol.387 , pp. 733-736
    • Heery, D.M.1    Kalkhoven, E.2    Hoare, S.3    Parker, M.G.4
  • 39
    • 0037135630 scopus 로고    scopus 로고
    • Bicalutamide functions as an androgen receptor antagonist by assembly of a transcriptionally inactive receptor
    • Masiello, D.; Cheng, S.; Bubley, G. J.; Lu, M. L.; Balk, S. P. Bicalutamide functions as an androgen receptor antagonist by assembly of a transcriptionally inactive receptor. J. Biol. Chem. 2002, 277, 26321-26326.
    • (2002) J. Biol. Chem , vol.277 , pp. 26321-26326
    • Masiello, D.1    Cheng, S.2    Bubley, G.J.3    Lu, M.L.4    Balk, S.P.5
  • 40
    • 0036218774 scopus 로고    scopus 로고
    • The amino terminus of the human AR is target for corepressor action and antihormone agonism
    • Dotzlaw, H.; Moehren, U.; Mink, S.; Cato, A. C.; Iniguez Lluhi, J. A.; Baniahmad, A. The amino terminus of the human AR is target for corepressor action and antihormone agonism. Mol. Endocrinol 2002, 16, 661-673.
    • (2002) Mol. Endocrinol , vol.16 , pp. 661-673
    • Dotzlaw, H.1    Moehren, U.2    Mink, S.3    Cato, A.C.4    Iniguez Lluhi, J.A.5    Baniahmad, A.6
  • 41
    • 27144466425 scopus 로고    scopus 로고
    • Antiandrogens prevent stable DNA-binding of the androgen receptor
    • Farla, P.; Hersmus, R.; Trapman, J.; Houtsmuller, A. B. Antiandrogens prevent stable DNA-binding of the androgen receptor. J. Cell. Sci. 2005, 118, 4187-1198.
    • (2005) J. Cell. Sci , vol.118 , pp. 4187-1198
    • Farla, P.1    Hersmus, R.2    Trapman, J.3    Houtsmuller, A.B.4
  • 42
    • 14844288915 scopus 로고    scopus 로고
    • The androgen receptor recruits nuclear receptor CoRepressor (N-CoR) in the presence of mifepristone via its N and C termini revealing a novel molecular mechanism for androgen receptor antagonists
    • Hodgson, M. C.; Astapova, I.; Cheng, S.; Lee, L. J.; Verhoeven, M. C.; Choi, E.; Balk, S. P.; Hollenberg, A. N. The androgen receptor recruits nuclear receptor CoRepressor (N-CoR) in the presence of mifepristone via its N and C termini revealing a novel molecular mechanism for androgen receptor antagonists. J. Biol. Chem. 2005, 280, 6511-6519.
    • (2005) J. Biol. Chem , vol.280 , pp. 6511-6519
    • Hodgson, M.C.1    Astapova, I.2    Cheng, S.3    Lee, L.J.4    Verhoeven, M.C.5    Choi, E.6    Balk, S.P.7    Hollenberg, A.N.8
  • 43
    • 33745472162 scopus 로고    scopus 로고
    • Free energy simulations of uncatalyzed DNA replication fidelity: Structure and stability of T.G and dTTP.G terminal DNA mismatches flanked by a single dangling nucleotide
    • Bren, U.; Martinek, V.; Florian, J. Free energy simulations of uncatalyzed DNA replication fidelity: structure and stability of T.G and dTTP.G terminal DNA mismatches flanked by a single dangling nucleotide. J. Phys. Chem. B 2006, 110, 10557-10566.
    • (2006) J. Phys. Chem. B , vol.110 , pp. 10557-10566
    • Bren, U.1    Martinek, V.2    Florian, J.3
  • 44
    • 18744402486 scopus 로고    scopus 로고
    • Computer simulations of protein functions: Searching for the molecular origin of the replication fidelity of DNA polymerases
    • Florian, J.; Goodman, M. F.; Warshel, A. Computer simulations of protein functions: searching for the molecular origin of the replication fidelity of DNA polymerases. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 6819-6824.
    • (2005) Proc. Natl. Acad. Sci. U.S.A , vol.102 , pp. 6819-6824
    • Florian, J.1    Goodman, M.F.2    Warshel, A.3
  • 45
    • 33746530513 scopus 로고    scopus 로고
    • Role of crystal-amorphous interaction in phase equilibria of crystal-amorphous polymer blends
    • Matkar, R. A.; Kyu, T. Role of crystal-amorphous interaction in phase equilibria of crystal-amorphous polymer blends. J. Phys. Chem. B. 2006, 110, 12728-12732.
    • (2006) J. Phys. Chem. B , vol.110 , pp. 12728-12732
    • Matkar, R.A.1    Kyu, T.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.