FFA1-selective agonistic activity based on docking simulation using FFA1 and GPR120 homology models

British Journal of Pharmacology

Volumn 168, Issue 7, 2013, Pages 1570-1583

  Takeuchi, Masato ^a   Hirasawa, Akira ^a   Hara, Takafumi ^a   Kimura, Ikuo ^a   Hirano, Tatsuya ^b   Suzuki, Takayoshi ^c   Miyata, Naoki ^b   Awaji, Takeo ^d   Ishiguro, Masaji ^e   Tsujimoto, Gozoh ^a  

^a KYOTO UNIVERSITY   (Japan)

^b NAGOYA CITY UNIVERSITY   (Japan)

^c KYOTO PREFECTURAL UNIVERSITY OF MEDICINE   (Japan)

^d SAITAMA MEDICAL UNIVERSITY   (Japan)

^e NIIGATA UNIVERSITY OF PHARMACY AND APPLIED LIFE SCIENCES   (Japan)

Author keywords

agonist; FFA1; G protein coupled receptor; GPR120; homology modelling

Indexed keywords

12 (PHENYL 2 PYRIDINYLAMINO) DODECANOIC ACID; CALCIUM ION; G PROTEIN COUPLED RECEPTOR 120; G PROTEIN COUPLED RECEPTOR 40; MITOGEN ACTIVATED PROTEIN KINASE; PROTEIN DERIVATIVE; SMALL INTERFERING RNA; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CORRELATION ANALYSIS; ENZYME ACTIVATION; ENZYME ACTIVITY; ENZYME INHIBITION; GENETIC TRANSFECTION; HUMAN; HUMAN CELL; HYDROGEN BOND; INSULIN RELEASE; MOLECULAR DOCKING; MOLECULAR RECOGNITION; MOUSE; NONHUMAN; PANCREAS ISLET BETA CELL; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN PHOSPHORYLATION; SITE DIRECTED MUTAGENESIS; STRUCTURE ACTIVITY RELATION;

ANIMALS; CALCIUM; CELL LINE; EXTRACELLULAR SIGNAL-REGULATED MAP KINASES; FATTY ACIDS, NONESTERIFIED; HUMANS; HYDROGEN BONDING; INSULIN; INSULIN-SECRETING CELLS; LAURIC ACIDS; LIGANDS; MICE; MOLECULAR DOCKING SIMULATION; MUTAGENESIS, SITE-DIRECTED; PHOSPHORYLATION; RECEPTORS, G-PROTEIN-COUPLED; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84875174029     PISSN: 00071188     EISSN: 14765381     Source Type: Journal    
DOI: 10.1111/j.1476-5381.2012.02052.x     Document Type: Article

References (32)

1. Akerman M, Houze J, Lin DCH, Liu J, Luo J, Medina JC, et al,. (2005). Arylmethoxyphenyl-alkylcarboxylic acids and related derivatives for use in treating metabolic disorders. Patent Application No. WO 2005/086661.
2. th Edition. Br J Pharmacol 164 (Suppl. 1): S1-S324.
3. Bharate SB, Rodge A, Joshi RK, Kaur J, Srinivasan S, Kumar SS, et al,. (2008). Discovery of diacylphloroglucinols as a new class of GPR40 (FFAR1) agonists. Bioorg Med Chem Lett 18: 6357-6361.
4. Briscoe CP, Tadayyon M, Andrews JL, Benson WG, Chambers JK, Eilert MM, et al,. (2003). The orphan G protein-coupled receptor GPR40 is activated by medium and long chain fatty acids. J Biol Chem 278: 11303-11311.
5. Briscoe CP, Peat AJ, McKeown SC, Corbett DF, Goetz AS, Littleton TR, et al,. (2006). Pharmacological regulation of insulin secretion in MIN6 cells through the fatty acid receptor GPR40: identification of agonist and antagonist small molecules. Br J Pharmacol 148: 619-628.
6. Davi M, Lebel H, (2008). One-pot approach for the synthesis of trans-cyclopropyl compounds from aldehydes. Application to the synthesis of GPR40 receptor agonists. Chem Commun (Camb) 40: 4974-4976.
7. Feng DD, Luo Z, Roh SG, Hernandez M, Tawadros N, Keating DJ, et al,. (2006). Reduction in voltage-gated K+ currents in primary cultured rat pancreatic beta-cells by linoleic acids. Endocrinology 147: 674-682.
8. Garrido DM, Corbett DF, Dwornik KA, Goetz AS, Littleton TR, McKeown SC, et al,. (2006). Synthesis and activity of small molecule GPR40 agonists. Bioorg Med Chem Lett 16: 1840-1845.
9. Hara T, Hirasawa A, Sun Q, Koshimizu TA, Itsubo C, Sadakane K, et al,. (2009a). Flow cytometry-based binding assay for GPR40 (FFAR1; free fatty acid receptor 1). Mol Pharmacol 75: 85-91.
10. Hara T, Hirasawa A, Sun Q, Sadakane K, Itsubo C, Iga T, et al,. (2009b). Novel selective ligands for free fatty acid receptors GPR120 and GPR40. Naunyn Schmiedebergs Arch Pharmacol 380: 247-255.
11. Hirasawa A, Tsumaya K, Awaji T, Katsuma S, Adachi T, Yamada M, et al,. (2005). Free fatty acids regulate gut incretin glucagon-like peptide-1 secretion through GPR120. Nat Med 11: 90-94.
12. Hirasawa A, Hara T, Katsuma S, Adachi T, Tsujimoto G, (2008). Free fatty acid receptors and drug discovery. Biol Pharm Bull 31: 1847-1851.
13. Ishiguro M, Oyama Y, Hirano T, (2004). Structural models of the photointermediates in the rhodopsin photocascade, lumirhodopsin, metarhodopsin I, and metarhodopsin II. Chembiochem 5: 298-310.
14. Itoh Y, Kawamata Y, Harada M, Kobayashi M, Fujii R, Fukusumi S, et al,. (2003). Free fatty acids regulate insulin secretion from pancreatic beta cells through GPR40. Nature 422: 173-176.
15. Kobilka BK, (2007). G protein coupled receptor structure and activation. Biochim Biophys Acta 1768: 794-807.
16. Lu SY, Jiang YJ, Lv J, Wu TX, Yu QS, Zhu WL, (2010). Molecular docking and molecular dynamics simulation studies of GPR40 receptor-agonist interactions. J Mol Graph Model 28: 766-774.
17. Milligan G, Stoddart LA, Brown AJ, (2006). G protein-coupled receptors for free fatty acids. Cell Signal 18: 1360-1365.
18. Nakamichi Y, Kikuta T, Ito E, Ohara-Imaizumi M, Nishiwaki C, Ishida H, et al,. (2003). PPARγ overexpression suppresses glucose-induced proinsulin biosynthesis and insulin release synergistically with pioglitazone in MIN6 cells. Biochem Biophys Res Commun 306: 832-836.
19. Poitout V, (2003). The ins and outs of fatty acids on the pancreatic beta cell. Trends Endocrinol Metab 14: 201-203.
20. Radestock S, Weil T, Renner S, (2008). Homology model-based virtual screening for GPCR ligands using docking and target-biased scoring. J Chem Inf Model 48: 1104-1117.
21. Rosenbaum DM, Rasmussen SG, Kobilka BK, (2009). The structure and function of G-protein-coupled receptors. Nature 459: 356-363.
22. Sasaki S, Kitamura S, Negoro N, Suzuki M, Tsujihata Y, Suzuki N, et al,. (2011). Design, synthesis, and biological activity of potent and orally available G protein-coupled receptor 40 agonists. J Med Chem 54: 1365-1378.
23. Shim JY, Welsh WJ, Howlett AC, (2003). Homology model of the CB1 cannabinoid receptor: sites critical for nonclassical cannabinoid agonist interaction. Biopolymers 71: 169-189.
24. Steneberg P, Rubins N, Bartoov-Shifman R, Walker MD, Edlund H, (2005). The FFA receptor GPR40 links hyperinsulinemia, hepatic steatosis, and impaired glucose homeostasis in mouse. Cell Metab 1: 245-258.
25. Stoddart LA, Smith NJ, Milligan G, (2008). International Union of Pharmacology. LXXI. Free fatty acid receptors FFA1, -2, and -3: pharmacology and pathophysiological functions. Pharmacol Rev 60: 405-417.
26. Sum CS, Tikhonova IG, Neumann S, Engel S, Raaka BM, Costanzi S, et al,. (2007). Identification of residues important for agonist recognition and activation in GPR40. J Biol Chem 282: 29248-292455.
27. Sun Q, Hirasawa A, Hara T, Kimura I, Adachi T, Awaji T, et al,. (2010). Structure-activity relationships of GPR120 agonists based on a docking simulation. Mol Pharmacol 78: 804-810.
28. Suzuki T, Igari S, Hirasawa A, Hata M, Ishiguro M, Fujieda H, et al,. (2008). Identification of G protein-coupled receptor 120-selective agonists derived from PPARgamma agonists. J Med Chem 51: 7640-7644.
29. Thomsen R, Christensen MH, (2006). MolDock: a new technique for high-accuracy molecular docking. J Med Chem 49: 3315-3321.
30. Tikhonova IG, Sum CS, Neumann S, Thomas CJ, Raaka BM, Costanzi S, et al,. (2007). Bidirectional, iterative approach to the structural delineation of the functional 'chemoprint' in GPR40 for agonist recognition. J Med Chem 50: 2981-2989.
31. Tsujihata Y, Ito R, Suzuki M, Harada A, Negoro N, Yasuma T, et al,. (2011). TAK-875, an orally available G protein-coupled receptor 40/free fatty acid receptor 1 agonist, enhances glucose-dependent insulin secretion and improves both postprandial and fasting hyperglycemia in type 2 diabetic rats. J Pharmacol Exp Ther 339: 228-237.
32. Xhaard H, Rantanen VV, Nyrönen T, Johnson MS, (2006). Molecular evolution of adrenoceptors and dopamine receptors: implications for the binding of catecholamines. J Med Chem 49: 1706-1719.