Structural basis for the improved potency of Peroxisome Proliferator-Activated Receptor (PPAR) agonists

ChemMedChem

Volumn 5, Issue 10, 2010, Pages 1707-1716

  Peng, Yi Hui ^a,b   Coumar, Mohane Selvaraj ^a   Leou, Jiun Shyang ^a   Wu, Jian Sung ^a   Shiao, Hui Yi ^a   Lin, Chia Hui ^a   Lin, Wen Hsing ^a   Lien, Tzu Wen ^a   Chen, Xin ^a   Hsu, John T A ^a,c   Chao, Yu Sheng ^a   Huang, Chien Fu ^d   Lyu, Ping Chiang ^b   Hsieh, Hsing Pang ^a   Wu, Su Ying ^a,b  

^a NATIONAL HEALTH RESEARCH INSTITUTES   (Taiwan)

^b NATIONAL TSING HUA UNIVERSITY   (Taiwan)

^c NATIONAL CHIAO TUNG UNIVERSITY   (Taiwan)

^d I SHOU UNIVERSITY   (Taiwan)

Author keywords

Diabetes; PPAR agonists; Structural biology; Structure activity relationships

Indexed keywords

1,2,3,4 TETRAHYDROQUINOLINE DERIVATIVE; 3 [5 [3 (3 PHENYL 7 PROPYLBENZO[D]ISOXAZOL 6 YLOXY)PROPOXY] 3,4 DIHYDRO 2H QUINOLIN 1 YL]PROPIONIC ACID; 3 [5 [3 (6 BENZOYL 1 PROPYLNAPHTHALEN 2 YLOXY)PROPOXY] 3,4 DIHYDRO 2H QUINOLIN 1 YL]PROPIONIC ACID; 3 [5 [3 (7 PROPYL 3 TRIFLUOROMETHYLBENZO[D]ISOXAZOL 6 YLOXY)PROPOXY] 3,4 DIHYDRO 2H QUINOLIN 1 YL]PROPIONIC ACID; 3 [5 [3 [4 (4 FLUOROBENZOYL) 2 PROPYLPHENOXY]PROPOXY] 3,4 DIHYDRO 2H QUINOLIN 1 YL]PROPIONIC ACID; 3 [5 [3 [4 (4 METHOXYBENZOYL) 2 PROPYLPHENOXY]PROPOXY] 3,4 DIHYDRO 2H QUINOLIN 1 YL]PROPIONIC ACID; 3 [5 [3 [4 (BIPHENYL 4 CARBONYL) 2 PROPYLPHENOXY]PROPOXY] 3,4 DIHYDRO 2H QUINOLIN 1 YL]PROPIONIC ACID; 3 [5 [3 [4 [4 (2 METHOXYETHOXY)BENZOYL] 2 PROPYLPHENOXY]PROPOXY] 3,4 DIHYDRO 2H QUINOLIN 1 YL]PROPIONIC ACID; 4 PHENYLBENZOPHENONE; [5 [3 [4 (BIPHENYL 4 YLCARBONYL)PHENOXY]PROPOXY] 1H INDOL 1 YL]ACETIC ACID; BENZOPHENONE DERIVATIVE; CARBOXYLIC ACID; INDOLE; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR AGONIST; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA; ROSIGLITAZONE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; DRUG CONFORMATION; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

BENZOPHENONES; BINDING SITES; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; HYDROGEN BONDING; INDOLEACETIC ACIDS; INDOLES; PPAR GAMMA; PROTEIN STRUCTURE, TERTIARY; STRUCTURE-ACTIVITY RELATIONSHIP; THERMODYNAMICS; THIAZOLIDINEDIONES;

EID: 77957687159     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201000194     Document Type: Article

References (22)

1. S. A. Kliewer, K. Umesono, D. J. Noonan, R. A. Heyman, R. M. Evans, Nature 1992, 358, 771-774.
2. J. P. Berger, T. E. Akiyama, P. T. Meinke, Trends Pharmacol. Sci. 2005, 26, 244-251.
3. a) R. T. Nolte, G. B. Wisely, S. Westin, J. E. Cobb, M. H. Lambert, R. Kurokawa, M. G. Rosenfeld, T. M. Willson, C. K. Glass, M. V. Milburn, Nature 1998, 395, 137-143;
4. b) H. E. Xu, M. H. Lambert, V. G. Montana, D. J. Parks, S. G. Blanchard, P. J. Brown, D. D. Sternbach, J. M. Lehmann, G. B. Wisely, T. M. Willson, S. A. Kliewer, M. V. Milburn, Mol. Cell 1999, 3, 397-403.
5. C. K. Glass, M. G. Rosenfeld, Genes Dev. 2000, 14, 121-141.
6. a) H. Yki-Jarvinen, N. Engl. J. Med. 2004, 351, 1106-1118;
7. b) I. W. Campbell, Curr. Mol. Med. 2005, 5, 349-363.
8. a) J. M. Lehmann, L. B. Moore, T. A. Smith-Oliver, W. O. Wilkison, T. M. Willson, S. A. Kliewer, J. Biol. Chem. 1995, 270, 12953-12 956;
9. b) P. Tontonoz, E. Hu, B. M. Spiegelman, Curr. Opin. Genet. Dev. 1995, 5, 571-576.
10. S. E. Nissen, K. Wolski, N. Engl. J. Med. 2007, 356, 2457-2471.
11. S. E. Nissen, K. Wolski, E. J. Topol, JAMA J. Am. Med. Assoc. 2005, 294, 2581-2586.
12. C. R. Waites, M. A. Dominick, T. P. Sanderson, B. E. Schilling, Toxicol. Sci. 2007, 100, 248-258.
13. N. Mahindroo, C. F. Huang, Y. H. Peng, C. C. Wang, C. C. Liao, T. W. Lien, S. K. Chittimalla, W. J. Huang, C. H. Chai, E. Prakash, C. P. Chen, T. A. Hsu, C. H. Peng, I. L. Lu, L. H. Lee, Y. W. Chang, W. C. Chen, Y. C. Chou, C. T. Chen, C. M. Goparaju, Y. S. Chen, S. J. Lan, M. C. Yu, X. Chen, Y. S. Chao, S. Y. Wu, H. P. Hsieh, J. Med. Chem. 2005, 48, 8194-8208.
14. C. H. Lin, Y. H. Peng, M. S. Coumar, S. K. Chittimalla, C. C. Liao, P. C. Lyn, C. C. Huang, T. W. Lien, W. H. Lin, J. T. Hsu, J. H. Cheng, X. Chen, J. S. Wu, Y. S. Chao, H. J. Lee, C. G. Juo, S. Y. Wu, H. P. Hsieh, J. Med. Chem. 2009, 52, 2618-2622.
15. N. Mahindroo, Y. H. Peng, C. H. Lin, U. K. Tan, E. Prakash, T. W. Lien, I. L. Lu, H. J. Lee, J. T. Hsu, X. Chen, C. C. Liao, P. C. Lyu, Y. S. Chao, S. Y. Wu, H. P. Hsieh, J. Med. Chem. 2006, 49, 6421-6424.
16. A. Srikrishna, T. J. Reddy, R. Viswajanani, Tetrahedron 1996, 52, 1631-1636.
17. N. Mahindroo, C. C. Wang, C. C. Liao, C. F. Huang, I. L. Lu, T. W. Lien, Y. H. Peng, W. J. Huang, Y. T. Lin, M. C. Hsu, C. H. Lin, C. H. Tsai, J. T. Hsu, X. Chen, P. C. Lyu, Y. S. Chao, S. Y. Wu, H. P. Hsieh, J. Med. Chem. 2006, 49, 1212-1216.
18. Z. Otwinowski, W. Minor in Methods in Enzymology, Vol. 276: Macromolecular Crystallography, Humana, Totowa, 1997, pp. 307-326.
19. A. Vagin, A. Teplyakov, J. Appl. Crystallogr. 1997, 30, 1022-1025.
20. G. N. Murshudov, A. A. Vagin, E. J. Dodson, Acta Crystallogr. Sect. D. Biol. Crystallogr. 1997, 53, 240-255.
21. T. A. Jones, J. Y. Zou, S. W. Cowan, M. Kjeldgaard, Acta Crystallogr. Sect. A Found Crystallogr. 1991, 47, 110-119.
22. R. P. Joosten, J. Salzemann, V. Bloch, H. Stockinger, A.-C. Berglund, C. Blanchet, E. Bongcam-Rudloff, C. Combet, A. L. Da Costa, G. Deleage, M. Diarena, R. Fabbretti, G. Fettahi, V. Flegel, A. Gisel, V. Kasam, T. Kervinen, E. Korpelainen, K. Mattila, M. Pagni, M. Reichstadt, V. Breton, I. J. Tickle, G. Vriend, J. Appl. Crystallogr. 2009, 42, 376-384.