Ligand-based in silico 3D-QSAR study of PPAR-c agonists

Medicinal Chemistry Research

Volumn 20, Issue 7, 2011, Pages 1005-1014

  Sonawane, Lalit Vijay ^a   Bari, Sanjaykumar Baburao ^a  

^a R C PATEL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH   (India)

Author keywords

3D QSAR; Pharmacophore modeling; PHASE; PPAR c; Thiazolidinedione

Indexed keywords

2,4 THIAZOLIDINEDIONE DERIVATIVE; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA AGONIST;

ARTICLE; DRUG STRUCTURE; HYDROGEN BOND; HYDROPHOBICITY; PHARMACOPHORE; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

EID: 85027949976     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-010-9428-9     Document Type: Article

References (40)

1. Amnerkar NA, Bhusari KP (2010) Synthesis, anticonvulsant activity and 3D-QSAR study of some prop-2-eneamido and 1-acetylpyrazolin derivatives of aminobenzothiazole. Eur Med Chem 45:149-159
2. Aronoff S, Rosenblatt S, Braithwaite S, Egan JW, Mathisen AL, Schneider RL (2000) Pioglitazone hydrochloride monotherapy improves glycemic control in the treatment of patients with type 2 diabetes: A 6-month randomized placebo-controlled doseresponse study. Diabetes Care 23:1605
3. Auwerx RS (1999) Peroxisome proliferator-activated receptorgamma: A versatile metabolic regulator. J Ann Med 31:342-351
4. Berger J, Moller DE (2002) The mechanisms of action of PPARs. Annu Rev Med 53:409-435 (Pubitemid 34177889)
5. Berger J, Wagner JA (2002) Physiological and therapeutic roles of peroxisome proliferator-activated receptors. Diabetes Technol Ther 4:163-174 (Pubitemid 34663479)
6. Bhat BA, Ponnala S, Sahu DP, Tiwari P, Tripathi BK, Srivastava AK (2004) Synthesis and antihyperglycemic activity profiles of novel thiazolidinedione derivative. Bioorg Med Chem 12:5857-5864 (Pubitemid 39388184)
7. Brooks DA, Etgen GJ, Rito CJ, Shuker AJ, Dominianni SJ, Warshawsky AM, Ardecky R, Paterniti JR, Tyhonas J, Karanewsky DS, Kauffman RF, Broderick CL, Oldham BA, Montrose-Rafizadeh C, Winneroski LL, Faul MM, McCarthy JR (2001) Design and synthesis of 2-methyl-2-{4-[2-(5-methyl-2-aryloxazol-4 yl)ethoxy]phenoxy}propionic acids: A new class of dual PPAR alpha/gamma agonists. J Med Chem 44:2061
8. Brown PJ, Smith-Oliver TA, Charifson PS, Tomkinsom NC, Fivush AM, Sternbach DD, Wade LE, Orband-Miller L, Parks DJ, Blanchard SG, Kliewer SA, Lehmann JM, Willson TM (1997) Identification of peroxisome proliferator- activated receptor ligands from a biased chemical library. Chem Biol 4:909-918 (Pubitemid 28050375)
9. Chakrabarti R, Vikramadithyan RK, Misra P, Hiriyan J, Raichur S, Damarla RK, Gershome C, Suresh J, Rajagopalan R (2003) Ragaglitazar: A novel PPAR-a & PPAR-c agonist with potent lipid lowering and insulin-sensitizing efficacy in animal models. Br Pharmacol 140:527-537 (Pubitemid 37330497)
10. de Duve C (1996) The peroxisome in retrospect. Ann N Y Acad Sci 804:1-10 (Pubitemid 27056597)
11. Desai RC, Han W, Metzger EJ, Bergman JP, Gratale DF, MacNaul KL, Berger JP, Doebber TW, Leung K, Moller DE, Heck JV, Sahoo SP (2003) 5-aryl thiazolidine-2,4-diones: Discovery of PPAR Dual a/c agonists as antidiabetic agents. Bioorg Med Chem Lett 13:2795-2798 (Pubitemid 36851572)
12. Dixon SL, Smondyrev AM, Knoll EH, Rao SN, Shaw DE, Friesner RA (2006a) PHASE: A new engine for pharmacophore perception, 3D QSAR model development, and 3D database screening: 1. Methodology and preliminary results. J Comput-Aided Mol Des 20:647-671 (Pubitemid 46023928)
13. Dixon SL, Smondyrev AM, Rao SN (2006b) PHASE: A novel approach to pharmacophore modeling and 3D database searching. Chem Biol Drug Des 67:370-372
14. Ebdrup S, Pettersson I, Rasmussen HB, Deussen HJ, Jensen AF, Mortensen SB, Fleckner J, Pridal L, Nygaard L, Sauerberg P (2003) Synthesis and biological and structural characterization of the dual-acting peroxisome proliferator-activated receptor alpha/ gamma agonist ragaglitazar. J Med Chem 46:1306
15. Etegen GJ, Oldham BA, Johnson WT, Broderick CL, Montrose CR, Brozinick JT, Misener EA, Bean JS, Bensch WR, Brooks DA, Shuker AJ, Rito CJ, Mccarthy JR, Ardecky RJ, Jyhonas JS, Dana SL, Bilakovics JM, Paterniti JR, Ogilvie KM, Liu S, Kauffman RF (2002) A tailored therapy for metabolic syndrome. Diabetes 51:1083-1087
16. Evans DA, Doman TN, Thorner DA, Bodkin MJ (2007) 3D QSAR methods: Phase and catalyst compared. J Chem Inf Model 47:1248-1257 (Pubitemid 46973738)
17. Forman BM, Chen J, Evans RM (1997) Hypolipidemic drugs, polyunsaturated fatty acids, and eicosanoids are ligands for peroxisome proliferator-activated receptors a and d. Proc Natl Acad Sci USA 94:4312-4318
18. Iwata Y, Miyamoto S, Takamura M, Yanagisawa H, Kasuya A (2001) Interaction between peroxisome proliferator-activated receptor g and its agonists: Docking study of oximes having 5-benzyl-2,4 thiazolidinedione. J Mol Graph Model 19:536-542
19. Kaminski GA, Friesner RA, Tirado-Rives J, Jorgensen WL (2001) Evaluation and reparameterization of the OPLS-AA force field for proteins via comparison with accurate quantum chemical calculations on peptides. J Phys Chem B 105(28):6474-6487 (Pubitemid 35339015)
20. Kliewer SA, Sundseth SS, Jones SA, Brown PJ, Wisely GB, Koble CS, Devchand P, Wahli W, Willson TM, Lenhard JM, Lehmann JM (1997) Fatty acids and eicosanoids regulate gene expression through direct interactions with peroxisome proliferator-activated receptors alpha and gamma. Proc Natl Acad Sci USA 94:4318-4323 (Pubitemid 27194239)
21. Knouff C, Auwerx J (2004) Peroxisome proliferator-activated receptor-gamma calls for activation in moderation: Lessons from genetics and pharmacology. Endocrine Rev 25:899-918 (Pubitemid 39657772)
22. Koyama H, Boueres JK, Han W, Metzger EJ, Bergman JP, Gratale DF, Miller DJ, Tolman RL, MacNaul KL, Berger JP, Doebber TW, Leung K, Moller DE, Hecka JV, Sahoo SP (2003) 5-aryl thiazolidine-2,4-diones as selective PPAR-c agonists. Bioorg Med Chem Lett 13:1801-1804 (Pubitemid 36561168)
23. Kun L, Regina B, Acton J, Ralph M (2005) Selective PPARc modulators with improved pharmacological profiles. Bioorg Med Chem Lett 15:2437-2440
24. Lehmann JM, Moore LB, Smith-Oliver TA, Wilkison WO, Willson TM, Kliewer SA (1995) An antidiabetic thiazolidinedione is a high affinity ligand for peroxisome proliferator-activated receptor #(PPAR#). J Biol Chem 270:12953-12956
25. Lehmann JM, Lenhard JM, Oliver BB, Ringold GM, Kliewer SA (1997) Peroxisome proliferator-activated receptors alpha and gamma are activated by indomethacin and other non-steroidal anti-inflammatory drugs. J Biol Chem 272:3406-3410
26. Lemberger T, Desvergne B, Wahli W (1996) Peroxisome proliferatoractivated receptors: A nuclear receptor signaling pathway in lipid physiology. Annu Rev Cell Dev Biol 12:335-363 (Pubitemid 26422717)
27. Ligprep 2.0 (2006) Schrodinger, LLC, New York, NY.
28. Lohray BB, Lohray VB, Bajji AC, Kalchar S, Poondra R, Padakanti S, Chakrabarti R, Vikramadithyan RK, Misra P, Suresh J, Mamidi NVSR, Rajagopalan R (2001) (-)3-[4-[2-(Phenoxazine-10-yl)ethoxy]phenyl]-2-ethoxypropanoic acid [(-) DRF 2725]: A dual PPAR agonist with potent antihyperglycemic and lipid modulating activity. J Med Chem 44:2675-2678 (Pubitemid 32852157)
29. MacroModel 9.1 (2006) Schrodinger, LLC, New York, NY.
30. Mathisen AL, Brockley (2000) The relationship of HbAlc and weight in the treatment of patients with type 2 diabetes. Diabetes 49(Suppl 1):A117
31. Murami K, Tobe K, Ide T, Mochizuki T, Ohashi M, Akanuma Y, Yazaki Y, Kadowaki T (1998) A novel insulin sensitizer acts as a coligand for peroxisome proliferator activated receptor-a (PPAR-a) and PPAR-c. Diabetes 47:1841-1847
32. Nolte RT, Wisely GB, Westin S, Cobb JE, Lambert MH, Kurokawa R, Rosenfeld MG, Willson TM, Glass CK, Milburn MV (1998) Ligand binding and co-activator assembly of the peroxisome proliferator-activated receptor-gamma. Nature 395:137-143 (Pubitemid 28425645)
33. Okuno A, Tamemoto H, Tobe K, Ueki K, Mori Y, Iwamoto K, Umesono K, Akanuma Y, Fujiwara T, Horikoshi H, Yazaki Y, Kadowaki T (1998) Troglitazone increases the number of small adipocytes without the change of white adipose tissue mass in obese Zucker rats. J Clin Invest 101:1354-1361 (Pubitemid 28145252)
34. Olefsky JM, Saltiel AR (2000) Reviews on PPAR and insulin resistance. Trends Endocrinol Metab 11:362
35. Phase (2007) version 8.0.
36. Shinkai H (2001) The chemical structure and pharmacological properties of a novel isoxazolidinedione insulin sensitizer, JTT-501. Nippon Rinsho 59:2207-2210
37. Sonawane LV, Bari SB (2010) PPARc-novel target in antidiabetic drug design. Int J Drug Des Dis 1(2):155-160
38. Spiegelman BM (1998) PPAR-c: Adipogenic regulator and thiazolidinedione receptor. Diabetes 47:507-514 (Pubitemid 28160438)
39. Willson TM, Brown PJ, Sternbach DD, Henke BR (2000) The PPARs: From orphan receptors to drug discovery. J Med Chem 43:527-550 (Pubitemid 30127149)
40. Yanagisawa H, Takamura M, Yamada E, Fujita S, Fujiwara T, Yachi M, Isobe A, Hagisawa Y (2000) Novel oximes having 5-benzyl-2, 4-thiazolidinedione as antihyperglycemic agents: Synthesis and structure activity relationship. Bioorg Med Chem Lett 10:373-375 (Pubitemid 30125193)