메뉴 건너뛰기




Volumn 47, Issue 21, 2004, Pages 4985-4988

11β-alkyl-Δ9-19-nortestosterone derivatives: High-affinity ligands and potent partial agonists of the androgen receptor

Author keywords

[No Author keywords available]

Indexed keywords

ANDROGEN RECEPTOR; ANDROSTANOLONE; ANTIANDROGEN; ANTIGESTAGEN; CYPROTERONE ACETATE; GLUCOCORTICOID ANTAGONIST; MIFEPRISTONE; N BUTYL 11 (3,17BETA DIHYDROXYESTRA 1,3,5(10) TRIEN 7ALPHA YL) N METHYLUNDECANAMIDE; NANDROLONE DERIVATIVE; PARTIAL AGONIST; RECOMBINANT PROTEIN; TESTOSTERONE; ANTINEOPLASTIC AGENT; DRUG DERIVATIVE; LIGAND; NANDROLONE;

EID: 4744346088     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0342515     Document Type: Article
Times cited : (9)

References (36)
  • 3
    • 0032512792 scopus 로고    scopus 로고
    • Partial Androgen Insensitivity and Correlations with the Predicted Three-Dimensional Structure of the Androgen Receptor Ligand-Binding Domain
    • Yong, E. L.; Tut, T. G.; Ghadessy, F. J.; Prins, G.; Ratnam, S. S. Partial Androgen Insensitivity and Correlations with the Predicted Three-Dimensional Structure of the Androgen Receptor Ligand-Binding Domain. Mol. Cell. Biol. 1998, 137, 41-50.
    • (1998) Mol. Cell. Biol. , vol.137 , pp. 41-50
    • Yong, E.L.1    Tut, T.G.2    Ghadessy, F.J.3    Prins, G.4    Ratnam, S.S.5
  • 4
    • 0034714276 scopus 로고    scopus 로고
    • Structural Evidence for Ligand Specificity in the Binding Domain of the Human Androgen Receptor
    • Matias, P. M.; Donner, P.; Coelho, R.; Thomaz, M.; Peixoto, C.; et al. Structural Evidence for Ligand Specificity in the Binding Domain of the Human Androgen Receptor. J. Biol. Chem. 2000, 275, 26164-26171.
    • (2000) J. Biol. Chem. , vol.275 , pp. 26164-26171
    • Matias, P.M.1    Donner, P.2    Coelho, R.3    Thomaz, M.4    Peixoto, C.5
  • 5
    • 0031594713 scopus 로고    scopus 로고
    • Intermolecular NH2-/carboxyl-terminal interactions in androgen receptor dimerization revealed by mutations that cause androgen insensitivity
    • Langley, E.; Kemppainen, J. A.; Wilson, E. M. Intermolecular NH2-/carboxyl-terminal interactions in androgen receptor dimerization revealed by mutations that cause androgen insensitivity. J. Biol. Chem. 1998, 273, 92-101.
    • (1998) J. Biol. Chem. , vol.273 , pp. 92-101
    • Langley, E.1    Kemppainen, J.A.2    Wilson, E.M.3
  • 7
    • 0028278076 scopus 로고
    • Frequent detection of codon 877 mutation in the androgen receptor gene in advanced prostate cancers
    • Gaddipati, J. P.; McLeod, D. G.; Heidenberg, H. B.; Sesterhenn, I. A.; Finger, M. J.; et al. Frequent detection of codon 877 mutation in the androgen receptor gene in advanced prostate cancers. Cancer Res. 1994, 54, 2861-2864.
    • (1994) Cancer Res. , vol.54 , pp. 2861-2864
    • Gaddipati, J.P.1    McLeod, D.G.2    Heidenberg, H.B.3    Sesterhenn, I.A.4    Finger, M.J.5
  • 8
    • 0028237201 scopus 로고
    • Mechanism of Antiandrogen Action: Conformational Changes of the Receptor
    • Kuil, C. W.; Mulder, E. Mechanism of Antiandrogen Action: Conformational Changes of the Receptor. Mol. Cell. Endocrinol. 1994, 102, R1-R5.
    • (1994) Mol. Cell. Endocrinol. , vol.102
    • Kuil, C.W.1    Mulder, E.2
  • 9
    • 0028910730 scopus 로고
    • Growth inhibition of androgen-insensitive human prostate carcinoma cells by a 19-norsteroid derivative agent, mifepristone
    • Lin, M. F.; Kawachi, M. H.; Stallcup, M. R.; Grunberg, S. M.; Lin, F. F. Growth inhibition of androgen-insensitive human prostate carcinoma cells by a 19-norsteroid derivative agent, mifepristone. Prostate 1995, 26, 194-204.
    • (1995) Prostate , vol.26 , pp. 194-204
    • Lin, M.F.1    Kawachi, M.H.2    Stallcup, M.R.3    Grunberg, S.M.4    Lin, F.F.5
  • 10
    • 0033984387 scopus 로고    scopus 로고
    • Antitumor activity of mifepristone in the human LNCaP, LNCaP-C4, and LNCaP-C4-2 prostate cancer models in nude mice
    • El Etreby, M. F.; Liang, Y.; Johnson, M. H.; Lewis, R. W. Antitumor activity of mifepristone in the human LNCaP, LNCaP-C4, and LNCaP-C4-2 prostate cancer models in nude mice. Prostate 2000, 42, 99-106.
    • (2000) Prostate , vol.42 , pp. 99-106
    • El Etreby, M.F.1    Liang, Y.2    Johnson, M.H.3    Lewis, R.W.4
  • 11
    • 1842514450 scopus 로고    scopus 로고
    • Mifepristone-induced secretion of transforming growth factor betal-induced apoptosis in prostate cancer cells
    • Liang, Y.; Eid, M. A.; El Etreby, F.; Lewis, R. W.; Kumar, M. V. Mifepristone-induced secretion of transforming growth factor betal-induced apoptosis in prostate cancer cells. Int. J. Oncol. 2002, 21, 1259-1267.
    • (2002) Int. J. Oncol. , vol.21 , pp. 1259-1267
    • Liang, Y.1    Eid, M.A.2    El Etreby, F.3    Lewis, R.W.4    Kumar, M.V.5
  • 12
    • 0346025352 scopus 로고    scopus 로고
    • Antiandrogen effects of mifepristone on coactivator and corepressor interactions with the androgen receptor
    • Song, L. N.; Coghlan, M.; Gelmann, E. P. Antiandrogen effects of mifepristone on coactivator and corepressor interactions with the androgen receptor. Mol. Endocrinol. 2004, 18, 70-85.
    • (2004) Mol. Endocrinol. , vol.18 , pp. 70-85
    • Song, L.N.1    Coghlan, M.2    Gelmann, E.P.3
  • 13
    • 0034727865 scopus 로고    scopus 로고
    • Synthesis and Biological Activity of a Novel, Highly Potent Progesterone Receptor Antagonist
    • Fuhrmann, U.; Hess-Stumpp, H.; Cleve, A.; Neef, G.; Schwede, W.; et al. Synthesis and Biological Activity of a Novel, Highly Potent Progesterone Receptor Antagonist. J. Med. Chem. 2000, 43, 5010-5016.
    • (2000) J. Med. Chem. , vol.43 , pp. 5010-5016
    • Fuhrmann, U.1    Hess-Stumpp, H.2    Cleve, A.3    Neef, G.4    Schwede, W.5
  • 14
    • 0038265311 scopus 로고    scopus 로고
    • The three-dimensional structures of antagonistic and agonistic forms of the glucocorticoid receptor ligand-binding domain: RU-486 induces a transconformation that leads to active antagonism
    • Kauppi, B.; Jakob, C.; Farnegardh, M.; Yang, J.; Ahola, H.; et al. The three-dimensional structures of antagonistic and agonistic forms of the glucocorticoid receptor ligand-binding domain: RU-486 induces a transconformation that leads to active antagonism. J. Biol. Chem. 2003, 278, 22748-22754.
    • (2003) J. Biol. Chem. , vol.278 , pp. 22748-22754
    • Kauppi, B.1    Jakob, C.2    Farnegardh, M.3    Yang, J.4    Ahola, H.5
  • 15
    • 0030667676 scopus 로고    scopus 로고
    • Molecular basis of agonism and antagonism in the oestrogen receptor
    • Brzozowski, A. M.; Pike, A. C.; Dauter, Z.; Hubbard, R. E.; Bonn, T.; et al. Molecular basis of agonism and antagonism in the oestrogen receptor. Nature 1997, 389, 753-758.
    • (1997) Nature , vol.389 , pp. 753-758
    • Brzozowski, A.M.1    Pike, A.C.2    Dauter, Z.3    Hubbard, R.E.4    Bonn, T.5
  • 16
    • 0032446607 scopus 로고    scopus 로고
    • The structural basis of estrogen receptor/coactivator recognition and the antagonism of this interaction by tamoxifen
    • Shiau, A. K.; Barstad, D.; Loria, P. M.; Cheng, L.; Kushner, P. J.; et al. The structural basis of estrogen receptor/coactivator recognition and the 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
  • 17
    • 0035099225 scopus 로고    scopus 로고
    • Structural Insights into the Mode of Action of a Pure Antiestrogen
    • Pike, A. C.; Brzozowski, A. M.; Walton, J.; Hubbard, R. E.; Thorsell, A.; et al. Structural Insights into the Mode of Action of a Pure Antiestrogen. Structure 2001, 9, 145-153.
    • (2001) Structure , vol.9 , pp. 145-153
    • Pike, A.C.1    Brzozowski, A.M.2    Walton, J.3    Hubbard, R.E.4    Thorsell, A.5
  • 18
    • 0038745558 scopus 로고    scopus 로고
    • Glucocorticoid receptor antagonism by cyproterone acetate and RU486
    • Honer, C.; Nam, K.; Fink, C.; Marshall, P.; Ksander, G.; et al. Glucocorticoid receptor antagonism by cyproterone acetate and RU486. Mol. Pharmacol. 2003, 63, 1012-1020.
    • (2003) Mol. Pharmacol. , vol.63 , pp. 1012-1020
    • Honer, C.1    Nam, K.2    Fink, C.3    Marshall, P.4    Ksander, G.5
  • 19
    • 0026701699 scopus 로고
    • ICI 182,780, a new antiestrogen with clinical potential
    • Wakeling, A. E.; Bowler, J. ICI 182,780, a new antiestrogen with clinical potential. J. Steroid Biochem. Mol. Biol. 1982, 43, 173-177.
    • (1982) J. Steroid Biochem. Mol. Biol. , vol.43 , pp. 173-177
    • Wakeling, A.E.1    Bowler, J.2
  • 20
    • 0035942197 scopus 로고    scopus 로고
    • Crystallographic structures of the ligand-binding domains of the androgen receptor and its T877A mutant complexed with the natural agonist dihydrotestosterone
    • Sack, J. S.; Kish, K. F.; Wang, C.; Attar, R. M.; Kiefer, S. E.; et al. Crystallographic structures of the ligand-binding domains of the androgen receptor and its T877A mutant complexed with the natural agonist dihydrotestosterone. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 4904-4909.
    • (2001) Proc. Natl. Acad. Sci. U.S.A. , vol.98 , pp. 4904-4909
    • Sack, J.S.1    Kish, K.F.2    Wang, C.3    Attar, R.M.4    Kiefer, S.E.5
  • 21
    • 0037187408 scopus 로고    scopus 로고
    • Structural basis for the glucocorticoid response in a mutant human androgen receptor (AR(ccr)) derived from an androgen-independent prostate cancer
    • Matias, P. M.; Carrondo, M. A.; Coelho, R.; Thomaz, M.; Zhao, X. Y.; et al. Structural basis for the glucocorticoid response in a mutant human androgen receptor (AR(ccr)) derived from an androgen-independent prostate cancer. J. Med. Chem. 2002, 45, 1439-1446.
    • (2002) J. Med. Chem. , vol.45 , pp. 1439-1446
    • Matias, P.M.1    Carrondo, M.A.2    Coelho, R.3    Thomaz, M.4    Zhao, X.Y.5
  • 22
    • 0019815673 scopus 로고
    • Enzymic Aromatization of Deuterium Labelled Testosterone and Androst-4-ene-3,17-dione
    • Holland, H. L.; Taylor, G. J. Enzymic Aromatization of Deuterium Labelled Testosterone and Androst-4-ene-3,17-dione. Can. J. Chem. 1981, 59, 2809-2819.
    • (1981) Can. J. Chem. , vol.59 , pp. 2809-2819
    • Holland, H.L.1    Taylor, G.J.2
  • 23
    • 0021659714 scopus 로고
    • Synthesis of Ent-17-(prop-1-ynyl-17β-hydroxy-11β-(4-N,N- dimethylamino)-phenyl)-4,9-estradien-3-one, the Antipode of RU-38 486
    • Ottow, E.; Beier, S.; Elger, W.; Henderson, D. A.; Neef, G.; et al. Synthesis of Ent-17-(prop-1-ynyl-17β-hydroxy-11β-(4-N,N-dimethylamino) -phenyl)-4,9-estradien-3-one, the Antipode of RU-38 486. Steroids 1984, 44, 519-530.
    • (1984) Steroids , vol.44 , pp. 519-530
    • Ottow, E.1    Beier, S.2    Elger, W.3    Henderson, D.A.4    Neef, G.5
  • 24
    • 0023025294 scopus 로고
    • Synthese von 3-Keto-4,9-diensteroiden mit polymeren Reagenzien
    • Ponsold, K. Synthese von 3-Keto-4,9-diensteroiden mit polymeren Reagenzien. Z. Chem. 1986, 26, 371.
    • (1986) Z. Chem. , vol.26 , pp. 371
    • Ponsold, K.1
  • 27
    • 0001152910 scopus 로고
    • Epoxidation of Estra-5 (10), 9 (11)-diene Derivatives; a Convenient Synthesis of 11β-Vinylestrone Acetate
    • Napolitano, E.; Fiaschi, R.; Hanson, R. N. Epoxidation of Estra-5 (10), 9 (11)-diene Derivatives; A Convenient Synthesis of 11β-Vinylestrone Acetate. Gazz. Chim. Ital. 1990, 120, 323-326.
    • (1990) Gazz. Chim. Ital. , vol.120 , pp. 323-326
    • Napolitano, E.1    Fiaschi, R.2    Hanson, R.N.3
  • 28
    • 0020427960 scopus 로고
    • Synthesis of 11β-Vinyl-19-norsteroids as Potent Progestins
    • Teutsch, G.; Belanger, A.; Philibert, D.; Tournemine, C. Synthesis of 11β-Vinyl-19-norsteroids as Potent Progestins. Steroids 1982, 39, 607-615.
    • (1982) Steroids , vol.39 , pp. 607-615
    • Teutsch, G.1    Belanger, A.2    Philibert, D.3    Tournemine, C.4
  • 29
    • 0019443088 scopus 로고
    • Regio and Stereospecific Synthesis of 11β-Substituted 19-Norsteroids: Influence of 11β-Substitution on Progesterone Receptor Affinity
    • Belanger, A.; Philibert, D.; Teutsch, G. Regio and Stereospecific Synthesis of 11β-Substituted 19-Norsteroids: Influence of 11β-Substitution on Progesterone Receptor Affinity. Steroids 1981, 37, 361-382.
    • (1981) Steroids , vol.37 , pp. 361-382
    • Belanger, A.1    Philibert, D.2    Teutsch, G.3
  • 30
    • 0034725648 scopus 로고    scopus 로고
    • FXXLF and WXXLF sequences mediate the NH2-terminal interaction with the ligand binding domain of the androgen receptor
    • He, B.; Kemppainen, J. A.; Wilson, E. M. FXXLF and WXXLF sequences mediate the NH2-terminal interaction with the ligand binding domain of the androgen receptor. J. Biol. Chem. 2000, 275, 22986-22994.
    • (2000) J. Biol. Chem. , vol.275 , pp. 22986-22994
    • He, B.1    Kemppainen, J.A.2    Wilson, E.M.3
  • 31
    • 0029560494 scopus 로고
    • Evidence for an Antiparallel Orientation of the Ligand-activated Human Androgen Receptor Dimer
    • Langley, E.; Zhou, Z.; Wilson, E. M. Evidence for an Antiparallel Orientation of the Ligand-activated Human Androgen Receptor Dimer. J. Biol. Chem. 1985, 270, 29983-29990.
    • (1985) J. Biol. Chem. , vol.270 , pp. 29983-29990
    • Langley, E.1    Zhou, Z.2    Wilson, E.M.3
  • 32
    • 0022799180 scopus 로고
    • The mouse glucocorticoid receptor: Mapping of functional domains by cloning, sequencing and expression of wild-type and mutant receptor proteins
    • Danielsen, M.; Northrop, J. P.; Ringold, G. M. The mouse glucocorticoid receptor: mapping of functional domains by cloning, sequencing and expression of wild-type and mutant receptor proteins. EMBO J. 1986, 5, 2513-2522.
    • (1986) EMBO J. , vol.5 , pp. 2513-2522
    • Danielsen, M.1    Northrop, J.P.2    Ringold, G.M.3
  • 33
    • 0024002556 scopus 로고
    • Luciferase reporter gene vectors for analysis of promoters and enhancers
    • Nordeen, S. K. Luciferase reporter gene vectors for analysis of promoters and enhancers. Biotechniques 1988, 6, 454-458.
    • (1988) Biotechniques , vol.6 , pp. 454-458
    • Nordeen, S.K.1
  • 34
    • 0025644325 scopus 로고
    • A mutation in the ligand binding domain of the androgen receptor of human LNCaP cells affects steroid binding characteristics and response to anti-androgens
    • Veldscholte, J.; Ris-Stalpers, C.; Kuiper, G. G.; Jenster, G.; Berrevoets, C.; et al. A mutation in the ligand binding domain of the androgen receptor of human LNCaP cells affects steroid binding characteristics and response to anti-androgens. Biochem. Biophys. Res. Commun. 1990, 173, 534-540.
    • (1990) Biochem. Biophys. Res. Commun. , vol.173 , pp. 534-540
    • Veldscholte, J.1    Ris-Stalpers, C.2    Kuiper, G.G.3    Jenster, G.4    Berrevoets, C.5
  • 35
    • 0029990959 scopus 로고    scopus 로고
    • Deoxyribonucleic acid-binding ability of androgen receptors in whole cells: Implications for the actions of androgens and antiandrogens
    • Kuil, C. W.; Mulder, E. Deoxyribonucleic acid-binding ability of androgen receptors in whole cells: implications for the actions of androgens and antiandrogens. Endocrinology 1998, 137, 1870-1877.
    • (1998) Endocrinology , vol.137 , pp. 1870-1877
    • Kuil, C.W.1    Mulder, E.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.