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Volumn 57, Issue 3, 2014, Pages 849-860

Glucocorticoid receptor modulators informed by crystallography lead to a new rationale for receptor selectivity, function, and implications for structure-based design

Author keywords

[No Author keywords available]

Indexed keywords

ACUTE DISEASE; ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; ARTHRITIS, EXPERIMENTAL; BENZOXEPINS; BINDING SITES; CARRAGEENAN; CELL LINE; CHRONIC DISEASE; COLLAGEN; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; EDEMA; HUMANS; INFLAMMATION; LIGANDS; MALE; MODELS, MOLECULAR; MOLECULAR CONFORMATION; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, GLUCOCORTICOID; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 84894090667     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm401616g     Document Type: Article
Times cited : (26)

References (45)
  • 1
    • 84894047420 scopus 로고
    • Synthetic analogs of the adrenal cortical steroids
    • In; Eisenstein, A. B. Little, Brown and Co. Boston, MA
    • Steelman, S. L.; Hirschmann, R. Synthetic analogs of the adrenal cortical steroids. In The Adrenal Cortex; Eisenstein, A. B., Ed.; Little, Brown and Co.: Boston, MA, 1967; pp 345-383.
    • (1967) The Adrenal Cortex , pp. 345-383
    • Steelman, S.L.1    Hirschmann, R.2
  • 2
    • 0027015374 scopus 로고
    • The cortisone era: Aspects of its impact. Some contributions of the Merck Laboratories
    • Hirschmann, R. The cortisone era: Aspects of its impact. Some contributions of the Merck Laboratories Steroids 1992, 57, 579-592
    • (1992) Steroids , vol.57 , pp. 579-592
    • Hirschmann, R.1
  • 3
    • 0025997018 scopus 로고
    • Medicinal chemistry in the Golden Age of biology. Lessons from steroid and peptide research
    • Hirschmann, R. Medicinal chemistry in the Golden Age of biology. Lessons from steroid and peptide research Angew. Chem., Int. Ed. Engl. 1991, 30, 1278-1301
    • (1991) Angew. Chem., Int. Ed. Engl. , vol.30 , pp. 1278-1301
    • Hirschmann, R.1
  • 4
    • 0032743286 scopus 로고    scopus 로고
    • Novel ligands of steroid hormone receptors
    • Coghlan, M. J.; Kort, M. E. Novel ligands of steroid hormone receptors Expert Opin. Ther. Pat. 1999, 9, 1523-1536
    • (1999) Expert Opin. Ther. Pat. , vol.9 , pp. 1523-1536
    • Coghlan, M.J.1    Kort, M.E.2
  • 5
    • 77952950546 scopus 로고    scopus 로고
    • Selective glucocorticoid receptor modulators
    • De Bosscher, K. Selective glucocorticoid receptor modulators J. Steroid Biochem. Mol. Biol. 2010, 120, 96-104
    • (2010) J. Steroid Biochem. Mol. Biol. , vol.120 , pp. 96-104
    • De Bosscher, K.1
  • 6
    • 77349101801 scopus 로고    scopus 로고
    • Pharmacological strategies for improving the efficacy and a review. Therapeutic ratio of glucocorticoids in inflammatory lung diseases
    • Newton, R.; Leigh, R.; Giembycz, M. A. Pharmacological strategies for improving the efficacy and a review. Therapeutic ratio of glucocorticoids in inflammatory lung diseases Pharmacol. Ther. 2010, 125, 286-327
    • (2010) Pharmacol. Ther. , vol.125 , pp. 286-327
    • Newton, R.1    Leigh, R.2    Giembycz, M.A.3
  • 7
    • 79957997176 scopus 로고    scopus 로고
    • Molecular mechanisms of glucocorticoid receptor signaling
    • Labeur, M.; Holsboer, F. Molecular mechanisms of glucocorticoid receptor signaling Medicina 2010, 70, 457-462
    • (2010) Medicina , vol.70 , pp. 457-462
    • Labeur, M.1    Holsboer, F.2
  • 8
    • 79960898889 scopus 로고    scopus 로고
    • Classic glucocorticoids versus non-steroidal glucocorticoid receptor modulators: Survival of the fittest regulator of the immune system?
    • De Bosscher, K.; Beck, I. M.; Haegeman, G. Classic glucocorticoids versus non-steroidal glucocorticoid receptor modulators: Survival of the fittest regulator of the immune system? Brain, Behav., Immun. 2010, 24, 1035-1042
    • (2010) Brain, Behav., Immun. , vol.24 , pp. 1035-1042
    • De Bosscher, K.1    Beck, I.M.2    Haegeman, G.3
  • 9
    • 0032870623 scopus 로고    scopus 로고
    • Dissociated glucocorticoids with anti-inflammatory potential repress interleukin-6 gene expression by a NFκB-dependent mechanism
    • Berghe, W. V.; Francesconi, E.; De Bosscher, K.; Resche-Rigon, M.; Haegeman, G. Dissociated glucocorticoids with anti-inflammatory potential repress interleukin-6 gene expression by a NFκB-dependent mechanism Mol. Pharmacol. 1999, 56, 797-806
    • (1999) Mol. Pharmacol. , vol.56 , pp. 797-806
    • Berghe, W.V.1    Francesconi, E.2    De Bosscher, K.3    Resche-Rigon, M.4    Haegeman, G.5
  • 10
    • 0032870623 scopus 로고    scopus 로고
    • Dissociated glucocorticoids with anti-inflammatory potential repress interleukin-6 gene expression by a nuclear factor-κB-dependent mechanism
    • Vanden Berghe, W.; Francesconi, E.; De Bosscher, K.; Resche-Rigon, M.; Haegeman, G. Dissociated glucocorticoids with anti-inflammatory potential repress interleukin-6 gene expression by a nuclear factor-κB-dependent mechanism Mol. Pharmacol. 1999, 56, 797-806
    • (1999) Mol. Pharmacol. , vol.56 , pp. 797-806
    • Vanden Berghe, W.1    Francesconi, E.2    De Bosscher, K.3    Resche-Rigon, M.4    Haegeman, G.5
  • 11
    • 0035253604 scopus 로고    scopus 로고
    • Therapeutic benefit of a dissociated glucocorticoid and the relevance of in vitro separation of transrepression from transactivation activity
    • Belvisi, M. G.; Wicks, S. L.; Battram, C. H.; Bottoms, S. E.; Redford, J. E.; Woodman, P.; Brown, T. J.; Webber, S. E.; Foster, M. L. Therapeutic benefit of a dissociated glucocorticoid and the relevance of in vitro separation of transrepression from transactivation activity J. Immunol. 2001, 166, 1975-1982
    • (2001) J. Immunol. , vol.166 , pp. 1975-1982
    • Belvisi, M.G.1    Wicks, S.L.2    Battram, C.H.3    Bottoms, S.E.4    Redford, J.E.5    Woodman, P.6    Brown, T.J.7    Webber, S.E.8    Foster, M.L.9
  • 12
  • 13
    • 84857362332 scopus 로고    scopus 로고
    • Maps and legends: The quest for dissociated ligands of the glucocorticoid receptor
    • Clark, A. R.; Belvisi, M. G. Maps and legends: The quest for dissociated ligands of the glucocorticoid receptor Pharmacol. Ther. 2012, 134, 54-67
    • (2012) Pharmacol. Ther. , vol.134 , pp. 54-67
    • Clark, A.R.1    Belvisi, M.G.2
  • 14
    • 79960729433 scopus 로고    scopus 로고
    • Selective glucocorticoid receptor modulators: Future of glucocorticoid immunosuppressive therapy?
    • Quax, R. A. M.; Peeters, R. P.; Feelders, R. A. Selective glucocorticoid receptor modulators: Future of glucocorticoid immunosuppressive therapy? Endocrinology 2011, 152, 2927-2929
    • (2011) Endocrinology , vol.152 , pp. 2927-2929
    • Quax, R.A.M.1    Peeters, R.P.2    Feelders, R.A.3
  • 18
    • 79959471462 scopus 로고    scopus 로고
    • Boehringer Ingleheim's selective glucocorticoid receptor agonist development candidate: Evaluation of WO2010141331, WO2010141332 and WO2010141333
    • Norman, P. Boehringer Ingleheim's selective glucocorticoid receptor agonist development candidate: Evaluation of WO2010141331, WO2010141332 and WO2010141333 Expert Opin. Ther. Pat. 2011, 21, 1137-1142
    • (2011) Expert Opin. Ther. Pat. , vol.21 , pp. 1137-1142
    • Norman, P.1
  • 19
    • 84882807314 scopus 로고    scopus 로고
    • Crystalline forms of 2,2,2-trifluoro-N-[(1R,2S)-1-[1-(4-fluorophenyl)-1H- indazol-5-yl]oxy-1-(3-methoxyphenyl)-2-propanyl]acetamide (AZD-5423)
    • Norman, P. Crystalline forms of 2,2,2-trifluoro-N-[(1R,2S)-1-[1-(4- fluorophenyl)-1H-indazol-5-yl]oxy-1-(3-methoxyphenyl)-2-propanyl]acetamide (AZD-5423) Expert Opin. Ther. Pat. 2013, 23, 1239-1245
    • (2013) Expert Opin. Ther. Pat. , vol.23 , pp. 1239-1245
    • Norman, P.1
  • 23
    • 51649120855 scopus 로고    scopus 로고
    • An intra/intermolecular Suzuki sequence to benzopyridyloxepines containing geometrically pure exocyclic tetrasubstituted alkenes
    • Carson, M. W.; Giese, M. W.; Coghlan, M. J. An intra/intermolecular Suzuki sequence to benzopyridyloxepines containing geometrically pure exocyclic tetrasubstituted alkenes Org. Lett. 2008, 10, 2701-2704
    • (2008) Org. Lett. , vol.10 , pp. 2701-2704
    • Carson, M.W.1    Giese, M.W.2    Coghlan, M.J.3
  • 24
    • 0026336420 scopus 로고
    • Advantages of triple therapy with mizoribine, cyclosporine and prednisolone over other types of triple and/or double therapy including cyclosporine for renal transplantation
    • Uchida, H.; Mita, K.; Bekku, Y.; Nishimura, Y.; Ishida, Y.; Watanabe, K.; Tomikawa, S.; Inoue, S.; Sugimoto, H.; Nagao, T. Advantages of triple therapy with mizoribine, cyclosporine and prednisolone over other types of triple and/or double therapy including cyclosporine for renal transplantation J. Toxicol. Sci. 1991, 16, 181-190
    • (1991) J. Toxicol. Sci. , vol.16 , pp. 181-190
    • Uchida, H.1    Mita, K.2    Bekku, Y.3    Nishimura, Y.4    Ishida, Y.5    Watanabe, K.6    Tomikawa, S.7    Inoue, S.8    Sugimoto, H.9    Nagao, T.10
  • 26
    • 33646455863 scopus 로고    scopus 로고
    • Cyclocarbopalladation of alkynes: A stereoselective method for preparing dibenzoxapine containing tetrasubstituted exocyclic alkenes
    • Yu, H.; Richey, R. N.; Carson, M. W.; Coghlan, M. J. Cyclocarbopalladation of alkynes: A stereoselective method for preparing dibenzoxapine containing tetrasubstituted exocyclic alkenes Org. Lett. 2006, 8, 1685-1688
    • (2006) Org. Lett. , vol.8 , pp. 1685-1688
    • Yu, H.1    Richey, R.N.2    Carson, M.W.3    Coghlan, M.J.4
  • 27
    • 39149083789 scopus 로고    scopus 로고
    • Stereoselective synthesis of dibenzoxapine containing tetrasubstituted exocyclic alkenes via cascade methylboronic acid coupling reactions
    • Yu, H.; Richey, R. N.; Mendiola, J.; Adeva, M.; Somoza, C.; May, S. A.; Carson, M. W.; Coghlan, M. J. Stereoselective synthesis of dibenzoxapine containing tetrasubstituted exocyclic alkenes via cascade methylboronic acid coupling reactions Tetrahedron Lett. 2008, 49, 1915-1918
    • (2008) Tetrahedron Lett. , vol.49 , pp. 1915-1918
    • Yu, H.1    Richey, R.N.2    Mendiola, J.3    Adeva, M.4    Somoza, C.5    May, S.A.6    Carson, M.W.7    Coghlan, M.J.8
  • 32
    • 84986454716 scopus 로고
    • Introduction of the methoxymethyl ether protecting group
    • Yardley, J. P.; Fletcher, H., III. Introduction of the methoxymethyl ether protecting group Synthesis 1976, 244
    • (1976) Synthesis , pp. 244
    • Yardley, J.P.1    Iii., F.H.2
  • 33
    • 79953741116 scopus 로고    scopus 로고
    • Recent progress on the studies of the true catalyst in the Heck reaction with supported Pd particles
    • Huang, L.; Wong, P. K. Recent progress on the studies of the true catalyst in the Heck reaction with supported Pd particles Curr. Org. Synth. 2010, 7, 599-613
    • (2010) Curr. Org. Synth. , vol.7 , pp. 599-613
    • Huang, L.1    Wong, P.K.2
  • 35
    • 70349644859 scopus 로고    scopus 로고
    • Indolobenzazepin-7-ones and 6-, 8-, and 9-membered ring derivatives as tubulin polymerization inhibitors: Synthesis and structure-activity relationship studies
    • Putey, A.; Popowycz, F.; Do, Q.-T.; Bernard, P.; Talapatra, S. K.; Kozielski, F.; Galmarini, C. M.; Joseph, B. Indolobenzazepin-7-ones and 6-, 8-, and 9-membered ring derivatives as tubulin polymerization inhibitors: Synthesis and structure-activity relationship studies J. Med. Chem. 2009, 52, 5916-5925
    • (2009) J. Med. Chem. , vol.52 , pp. 5916-5925
    • Putey, A.1    Popowycz, F.2    Do, Q.-T.3    Bernard, P.4    Talapatra, S.K.5    Kozielski, F.6    Galmarini, C.M.7    Joseph, B.8
  • 38
    • 77649243639 scopus 로고    scopus 로고
    • BOL-303242-X, a novel selective glucocorticoid receptor agonist, with full anti-inflammatory properties in human ocular cells
    • Zhang, J.-Z.; Cavet, M. E.; VanDerMeid, K. R.; Salvador-Silva, M.; Lopez, F. J.; Ward, K. W. BOL-303242-X, a novel selective glucocorticoid receptor agonist, with full anti-inflammatory properties in human ocular cells Mol. Vision 2009, 15, 2606-2616
    • (2009) Mol. Vision , vol.15 , pp. 2606-2616
    • Zhang, J.-Z.1    Cavet, M.E.2    Vandermeid, K.R.3    Salvador-Silva, M.4    Lopez, F.J.5    Ward, K.W.6
  • 39
    • 0041766163 scopus 로고    scopus 로고
    • Carrageenan-induced paw edema in the rat and mouse
    • Morris, C. J. Carrageenan-induced paw edema in the rat and mouse Methods Mol. Biol. 2003, 225, 115-121
    • (2003) Methods Mol. Biol. , vol.225 , pp. 115-121
    • Morris, C.J.1
  • 40
    • 0008044948 scopus 로고    scopus 로고
    • Murine collagen-induced arthritis
    • In; Morgan, D. W. Marshall, L. A. Birkhauser Verlag: Basel, Switzerland
    • Van Den Berg, W. B.; Joosten, L. A. B. Murine collagen-induced arthritis. In In Vivo Models of Inflammation; Morgan, D. W.; Marshall, L. A., Eds.; Birkhauser Verlag: Basel, Switzerland, 1999; pp 51-75.
    • (1999) Vivo Models of Inflammation , pp. 51-75
    • Van Den Berg, W.B.1    Joosten, L.A.B.2
  • 42
    • 45749101311 scopus 로고    scopus 로고
    • X-ray crystal structure of the novel enhanced-affinity glucocorticoid agonist fluticasone furoate in the glucocorticoid receptor-ligand binding domain
    • Biggadike, K.; Bledsoe, R. K.; Hassell, A. M.; Kirk, B. E.; McLay, I. M.; Shewchuk, L. M.; Stewart, E. L. X-ray crystal structure of the novel enhanced-affinity glucocorticoid agonist fluticasone furoate in the glucocorticoid receptor-ligand binding domain J. Med. Chem. 2008, 51, 3349-3352
    • (2008) J. Med. Chem. , vol.51 , pp. 3349-3352
    • Biggadike, K.1    Bledsoe, R.K.2    Hassell, A.M.3    Kirk, B.E.4    McLay, I.M.5    Shewchuk, L.M.6    Stewart, E.L.7
  • 43
    • 73249124826 scopus 로고    scopus 로고
    • Molecular switch in the glucocorticoid receptor: Active and passive antagonist conformations
    • Schoch, G. A.; D'Arcy, B.; Stihle, M.; Burger, D.; Bar, D.; Benz, J.; Thoma, R.; Ruf, A. Molecular switch in the glucocorticoid receptor: Active and passive antagonist conformations J. Mol. Biol. 2010, 395, 568-577
    • (2010) J. Mol. Biol. , vol.395 , pp. 568-577
    • Schoch, G.A.1    D'Arcy, B.2    Stihle, M.3    Burger, D.4    Bar, D.5    Benz, J.6    Thoma, R.7    Ruf, A.8


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