AMG 837: A novel GPR40/FFA1 agonist that enhances insulin secretion and lowers glucose levels in rodents

PLoS ONE

Volumn 6, Issue 11, 2011, Pages

  Lin, Daniel C H ^a   Zhang, Jane ^a   Zhuang, Run ^a   Li, Frank ^a   Nguyen, Kathy ^a   Chen, Michael ^a   Tran, Thanhvien ^a   Lopez, Edwin ^a   Lu, Jenny Ying Lin ^a   Li, Xiaoyan Nina ^a   Tang, Liang ^a   Tonn, George R ^a   Swaminath, Gayathri ^a   Reagan, Jeff D ^a   Chen, Jin Long ^a   Tian, Hui ^a   Lin, Yi Jyun ^a   Houze, Jonathan B ^a   Luo, Jian ^a  

^a AMGEN INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 [4 [[4' (TRIFLUOROMETHYL)BIPHENYL 3 YL]METHOXY]PHENYL]HEX 4 YNOIC ACID; AMG 837; ANTIDIABETIC AGENT; CALCIUM ION; G PROTEIN COUPLED RECEPTOR 40; GLUCOSE; GUANOSINE 5' O (3 THIOTRIPHOSPHATE); INOSITOL PHOSPHATE; INSULIN; UNCLASSIFIED DRUG; BIPHENYL DERIVATIVE; G PROTEIN COUPLED RECEPTOR; GPR40 PROTEIN, MOUSE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; AREA UNDER THE CURVE; ARTICLE; CALCIUM TRANSPORT; CONTROLLED STUDY; DOSE RESPONSE; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG MECHANISM; DRUG MEGADOSE; DRUG POTENCY; GLUCOSE BLOOD LEVEL; GLUCOSE TOLERANCE TEST; HUMAN; HUMAN CELL; HYPERGLYCEMIA; IN VITRO STUDY; IN VIVO STUDY; INSULIN RELEASE; LOW DRUG DOSE; MALE; MAXIMUM PLASMA CONCENTRATION; MOUSE; NONHUMAN; PANCREAS ISLET BETA CELL; POSTPRANDIAL STATE; PROTEIN BINDING; RAT; RODENT; SINGLE DRUG DOSE; TREATMENT DURATION; ANIMAL; DRUG EFFECT; DRUG POTENTIATION; PANCREAS ISLET; SECRETION; SPRAGUE DAWLEY RAT; ZUCKER RAT;

RATTUS; RODENTIA;

ANIMALS; BIPHENYL COMPOUNDS; BLOOD GLUCOSE; GLUCOSE TOLERANCE TEST; HYPOGLYCEMIC AGENTS; INSULIN; ISLETS OF LANGERHANS; MICE; POSTPRANDIAL PERIOD; RATS; RATS, SPRAGUE-DAWLEY; RATS, ZUCKER; RECEPTORS, G-PROTEIN-COUPLED;

EID: 80555154306     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0027270     Document Type: Article

References (37)

1. Itoh Y, Kawamata Y, Harada M, Kobayashi M, Fujii R, et al. (2003) Free fatty acids regulate insulin secretion from pancreatic beta cells through GPR40. Nature 422: 173-176.
2. Briscoe CP, Tadayyon M, Andrews JL, Benson WG, Chambers JK, 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.
3. Latour MG, Alquier T, Oseid E, Tremblay C, Jetton TL, et al. (2007) GPR40 is necessary but not sufficient for fatty acid stimulation of insulin secretion in vivo. Diabetes 56: 1087-1094.
4. Edfalk S, Steneberg P, Edlund H, (2008) Gpr40 is expressed in enteroendocrine cells and mediates free fatty acid stimulation of incretin secretion. Diabetes 57: 2280-2287.
5. Alquier T, Peyot ML, Latour MG, Kebede M, Sorensen CM, et al. (2009) Deletion of GPR40 impairs glucose-induced insulin secretion in vivo in mice without affecting intracellular fuel metabolism in islets. Diabetes 58: 2607-2615.
6. Rendell M, (2004) The role of sulphonylureas in the management of type 2 diabetes mellitus. Drugs 64: 1339-1358.
7. Fujiwara K, Maekawa F, Yada T, (2005) Oleic acid interacts with GPR40 to induce Ca2+ signaling in rat islet beta-cells: mediation by PLC and L-type Ca2+ channel and link to insulin release. Am J Physiol Endocrinol Metab 289: E670-677.
8. Feng DD, Luo Z, Roh SG, Hernandez M, Tawadros N, et al. (2006) Reduction in voltage-gated K+ currents in primary cultured rat pancreatic beta-cells by linoleic acids. Endocrinology 147: 674-682.
9. Briscoe CP, Peat AJ, McKeown SC, Corbett DF, Goetz AS, 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.
10. Bharate SB, Rodge A, Joshi RK, Kaur J, Srinivasan S, et al. (2008) Discovery of diacylphloroglucinols as a new class of GPR40 (FFAR1) agonists. Bioorg Med Chem Lett 18: 6357-6361.
11. Tan CP, Feng Y, Zhou YP, Eiermann GJ, Petrov A, et al. (2008) Selective small-molecule agonists of G protein-coupled receptor 40 promote glucose-dependent insulin secretion and reduce blood glucose in mice. Diabetes 57: 2211-2219.
12. Tikhonova IG, Sum CS, Neumann S, Engel S, Raaka BM, et al. (2008) Discovery of novel agonists and antagonists of the free fatty acid receptor 1 (FFAR1) using virtual screening. J Med Chem 51: 625-633.
13. Christiansen E, Urban C, Merten N, Liebscher K, Karlsen KK, et al. (2008) Discovery of potent and selective agonists for the free fatty acid receptor 1 (FFA(1)/GPR40), a potential target for the treatment of type II diabetes. J Med Chem 51: 7061-7064.
14. Sasaki S, Kitamura S, Negoro N, Suzuki M, Tsujihata Y, 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.
15. Negoro N, Sasaki S, Mikami S, Ito M, Suzuki M, et al. (2010) Discovery of TAK-875: A Potent, Selective, and Orally Bioavailable GPR40 Agonist. ACS Medicinal Chemistry Letters 1: 290-294.
16. Naik HVM, Wu J, Viswanathan P, Dote N, Higuchi T, Leifke E, (2011) Safety, Tolerability, Pharmacokinetics, and Pharmacodynamic Properties of the GPR40 Agonist TAK-875: Results From a Double-Blind, Placebo-Controlled Single Oral Dose Rising Study in Healthy Volunteers. J Clin Pharmacol.
17. Tomita T, Masuzaki H, Noguchi M, Iwakura H, Fujikura J, et al. (2005) GPR40 gene expression in human pancreas and insulinoma. Biochem Biophys Res Commun 338: 1788-1790.
18. Del Guerra S, Bugliani M, D'Aleo V, Del Prato S, Boggi U, et al. G-protein-coupled receptor 40 (GPR40) expression and its regulation in human pancreatic islets: the role of type 2 diabetes and fatty acids. Nutr Metab Cardiovasc Dis 20: 22-25.
19. Ogawa T, Hirose H, Miyashita K, Saito I, Saruta T, (2005) GPR40 gene Arg211His polymorphism may contribute to the variation of insulin secretory capacity in Japanese men. Metabolism 54: 296-299.
20. Hamid YH, Vissing H, Holst B, Urhammer SA, Pyke C, et al. (2005) Studies of relationships between variation of the human G protein-coupled receptor 40 Gene and Type 2 diabetes and insulin release. Diabet Med 22: 74-80.
21. Vettor R, Granzotto M, De Stefani D, Trevellin E, Rossato M, et al. (2008) Loss-of-function mutation of the GPR40 gene associates with abnormal stimulated insulin secretion by acting on intracellular calcium mobilization. J Clin Endocrinol Metab 93: 3541-3550.
22. Nagasumi K, Esaki R, Iwachidow K, Yasuhara Y, Ogi K, et al. (2009) Overexpression of GPR40 in pancreatic beta-cells augments glucose-stimulated insulin secretion and improves glucose tolerance in normal and diabetic mice. Diabetes 58: 1067-1076.
23. DeLapp NW, McKinzie JH, Sawyer BD, Vandergriff A, Falcone J, et al. (1999) Determination of [35S]guanosine-5′-O-(3-thio)triphosphate binding mediated by cholinergic muscarinic receptors in membranes from Chinese hamster ovary cells and rat striatum using an anti-G protein scintillation proximity assay. J Pharmacol Exp Ther 289: 946-955.
24. Ionescu E, Sauter JF, Jeanrenaud B, (1985) Abnormal oral glucose tolerance in genetically obese (fa/fa) rats. Am J Physiol 248: E500-506.
25. Terrettaz J, Assimacopoulos-Jeannet F, Jeanrenaud B, (1986) Severe hepatic and peripheral insulin resistance as evidenced by euglycemic clamps in genetically obese fa/fa rats. Endocrinology 118: 674-678.
26. Madiraju SR, Poitout V, (2007) G protein-coupled receptors and insulin secretion: 119 and counting. Endocrinology 148: 2598-2600.
27. Ahren B, (2009) Islet G protein-coupled receptors as potential targets for treatment of type 2 diabetes. Nat Rev Drug Discov 8: 369-385.
28. Cornish J, MacGibbon A, Lin JM, Watson M, Callon KE, et al. (2008) Modulation of osteoclastogenesis by fatty acids. Endocrinology 149: 5688-5695.
29. Flodgren E, Olde B, Meidute-Abaraviciene S, Winzell MS, Ahren B, et al. (2007) GPR40 is expressed in glucagon producing cells and affects glucagon secretion. Biochem Biophys Res Commun 354: 240-245.
30. Cartoni C, Yasumatsu K, Ohkuri T, Shigemura N, Yoshida R, et al. (2010) Taste preference for fatty acids is mediated by GPR40 and GPR120. J Neurosci 30: 8376-8382.
31. Boneva NB, Kaplamadzhiev DB, Sahara S, Kikuchi H, Pyko IV, et al. (2009) Expression of fatty acid-binding proteins in adult hippocampal neurogenic niche of postischemic monkeys. Hippocampus.
32. Hitchcock SA, Pennington LD, (2006) Structure-brain exposure relationships. J Med Chem 49: 7559-7583.
33. Kelder J, Grootenhuis PD, Bayada DM, Delbressine LP, Ploemen JP, (1999) Polar molecular surface as a dominating determinant for oral absorption and brain penetration of drugs. Pharm Res 16: 1514-1519.
34. Pajouhesh H, Lenz GR, (2005) Medicinal chemical properties of successful central nervous system drugs. NeuroRx 2: 541-553.
35. 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.
36. Swift S, Lorens J, Achacoso P, Nolan GP, (2001) Rapid Production of Retroviruses for Efficient Gene Delivery to Mammalian Cells Using 293T Cell-Based Systems. Current Protocols in Immunology pp. 10.17.14-10.17.29.
37. Walker SD, Borths CJ, DiVirgilio E, Huang L, Liu P, et al. (2011) Development of a Scalable Synthesis of a GPR40 Agonist. Organic Process and Development 15: 570-580.