GW627368X ((N-{2-[4-(4,9-diethoxy-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2- yl)phenyl]acetyl} benzene sulphonamide): A novel, potent and selective prostanoid EP 4 receptor antagonist

British Journal of Pharmacology

Volumn 148, Issue 3, 2006, Pages 326-339

  Wilson, Richard J ^a   Giblin, Gerard M P ^a   Roomans, Susan ^a   Rhodes, Sharron A ^a   Cartwright, Kerri Ann ^a   Shield, Vanessa J ^a   Brown, Jason ^a   Wise, Alan ^a   Chowdhury, Jannatara ^a   Pritchard, Sara ^a   Coote, Jim ^b   Noel, Lloyd S ^c   Kenakin, Terry ^c   Burns Kurtis, Cynthia L ^c   Morrison, Valerie ^a   Gray, David W ^a   Giles, Heather ^d  

^a GLAXOSMITHKLINE   (United Kingdom)

^b Cell Biology Unit   (United Kingdom)

^c GLAXOSMITHKLINE   (United States)

^d TEXAS BIOTECHNOLOGY CORPORATION   (United States)

Author keywords

Antagonist; Competitive; EP 4; GW627368X; Prostanoid; Receptor

Indexed keywords

15 HYDROXY 11ALPHA,9ALPHA EPOXYMETHANOPROSTA 5,13 DIENOIC ACID; GW 627368X; ILOPROST; N [2 [4 (4,9 DIETHOXY 1 OXO 1,3 DIHYDRO 2H BENZO[F]ISOINDOL 2 YL)PHENYL]ACETYL]BENZENE SULPHONAMIDE; PHENYLEPHRINE; PROSTAGLANDIN E2; PROSTANOID CRTH2 RECEPTOR; PROSTANOID EP2 RECEPTOR; PROSTANOID EP3 RECEPTOR; PROSTANOID FP RECEPTOR; PROSTANOID IP RECEPTOR; PROSTANOID RECEPTOR; RECEPTOR BLOCKING AGENT; RECOMBINANT PROTEIN; UNCLASSIFIED DRUG;

ANIMAL CELL; AORTA; ARTICLE; BINDING AFFINITY; BIOASSAY; CELL STRAIN HEK293; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG EFFECT; DRUG POTENCY; DRUG POTENTIATION; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; FEMALE; GUINEA PIG; HUMAN; HUMAN CELL; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; PROTEIN EXPRESSION; RABBIT; RADIOASSAY; SAPHENOUS VEIN; THROMBOCYTE; THROMBOCYTE AGGREGATION; VENOCONSTRICTION;

ANIMALS; AORTA; BENZENE DERIVATIVES; CELL LINE; DINOPROSTONE; GUINEA PIGS; HUMANS; INDOLES; ISOINDOLES; PLATELET AGGREGATION; RABBITS; RADIOLIGAND ASSAY; RECEPTORS, PROSTAGLANDIN E; RECEPTORS, PROSTAGLANDIN E, EP4 SUBTYPE; RECEPTORS, THROMBOXANE; SAPHENOUS VEIN; SULFONAMIDES; SWINE;

EID: 33744490979     PISSN: 00071188     EISSN: 14765381     Source Type: Journal    
DOI: 10.1038/sj.bjp.0706726     Document Type: Article

References (43)

1. ABRAMOVITZ, M., ADAM, M., BOIE, Y., CARRIERE, D.D., GODBOUT, C., LAMONTAGNE, S., ROCHETTE, C., SAWYER, N., TREMBLAY, N.M., BELLEY, M., GALLANT, M., DUFRESNE, C., GAREAU, Y., RUEL, R., JUTEAU, H., LABELLE, M., OUIMET, N. & METTERS, K. (2000). The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs. Biochim. Biophys. Acta., 1483, 285-293.
2. ABRAMOVITZ, M., ADAM, M., BOIE, Y., GRYGORCZYK, R., RUSHMORE, T.H., NGUYEN, T., FUNK, C.D., BASTIEN, L., SAWYER, N., ROCHETTE, C., SLIPETZ, D.M. & METTERS, K.M. (1995). Human prostanoid receptors: cloning and characterization. Adv. Prost. Thromb. Leuk. Res., 23, 499-504.
3. 3 prostanoid receptor. FEBS Letts., 338, 170-174.
4. ARUNLAKSHANA, O. & SCHILD, H.O. (1959). Some quantitative uses of drug antagonists. Br. J. Pharmacol., 14, 48-58.
5. 4 receptor. Bioorg. Med. Chem. Letts., 13, 1129-1132.
6. BIRDSALL, N.J., COHEN, F., LAZARENO, S. & MATSUI, H. (1995). Allosteric regulation of G-protein-linked receptors. Biochem. Soc. Trans., 23, 108-111.
7. BOIE, Y., SAWYER, N., SLIPETZ, D.M., METTERS, K.M. & ABRAMOVITZ, M. (1995). Molecular cloning and characterization of the human prostanoid DP receptor. J. Biol. Chem., 270, 18910-18916.
8. 2. Circulation, 72, 1208-1218.
9. 50) of an enzyme reaction. Biochem. Pharmacol., 22, 3099-3108.
10. 4 antagonist, AH 22921. In: Advances in Prostaglandin, Thromboxane and Leukotriene Research. eds. Samuelsson, B., Paoletti, R. & Ramwell, P. Vol. 23. pp. 241-246. New York: Raven.
11. COLEMAN, R.A., SMITH, W.L. & NARUMIYA, S. (1994). International Union of Pharmacology VIII. Classification of prostanoid receptors: properties, distribution and structure of the receptors and their subtypes. Pharmacol. Rev., 46, 205-229.
12. 4 prostaglandin receptors coupled positively to adenylyl cyclase in Chinese hamster ovary cells: pharmacological characterization. Prost. Leuk. Essent. Fatty Acids, 62, 21-26.
13. 4 prostanoid receptor-mediated vasodilatation of human middle cerebral arteries. Br J. Pharmacol., 141, 580-585.
14. GIBLIN, G.M.P., WILSON, R.J., FOORD, S.M., SWARBRICK, M., WALKER, A., BAMFORD, M., ROOMANS, S., MASON, A., MILLER, N., JONES, H., SHANAHAN, S., RASMUSSEN, S., SMITH, L., SPALDING, D., RANSHAW, L., FENWICK, R., ANCLIFF, R., SAEZ, V., FRYE, S., STRATTON, S., LEWELL, X., CARTWRIGHT, K.A., RHODES, S., ROBERTS, N. & GREEN, R. (2002). A Novel, selective, non-prostanoid EP4 receptor antagonist. Poster at 224th ACS Natl Meet (August 18-22, 2002, Boston) Abst MEDI-306.
15. 4 receptor antagonists. J. Med. Chem., 48, 3103-3106.
16. 2 selectively induces chemotaxis in T-helper type 2 cells, eosinophils, and basophils via seven-transmembrane receptor CRTH2. J. Exp. Med., 193, 225-261.
17. 60 to Leu mutation. J. Clin. Invest., 97, 949-956.
18. HUGHES, G.C., POST, M.J., SIMONS, M. & ANNEX, B.H. (2003). Translational physiology: porcine models of human coronary artery disease: implications for preclinical trials of therapeutic angiogenesis. J. App. Physiol., 94, 1689-1701.
19. JONES, R.L. & CHAN, K.M. (2005). Investigation of the agonist activity of prostacyclin analogues on prostanoid EP4 receptors using GW 627368 and taprostene: evidence for species differences. Prost. Leuk. Essent. Fatty Acids., 72, 289-299.
20. 3 Subtype generated by alternative messenger RNA splicing - multiple second messenger systems and tissue-specific distributions. Mol. Pharmacol., 48, 869-879.
21. LAZARENO, S. & BIRDSALL, N.J. (1995). Detection, quantitation, and verification of allosteric interactions of agents with labeled and unlabeled ligands at G protein-coupled receptors: interactions of strychnine and acetylcholine at muscarinic receptors. Mol. Pharmacol., 48, 362-378.
22. LEFF, P. (1996). The two-state model of agonist action: challenges to pharmacological receptor theory. Proc. Western Pharmacol. Soc., 39, 67-68.
23. LEW, M.J. & ANGUS, J.A. (1985). Analysis of competitive agonist-antagonist interactions by nonlinear regression. Trends Pharmacol. Sci., 16, 328-337.
24. 2 agonist stimulates local bone formation and enhances fracture healing. J. Bone Min. Res., 18, 2033-2042.
25. LUNDSTROM, K. (2002). Semliki forest virus-based expression for versatile use in receptor research. J. Recept. Sig. Trans., 22, 229-240.
26. LYDFORD, S.J., MCKECHNIE, K.C.W. & LEFF, P. (1996). Interaction of BW A868C, a prostanoid DP-receptor antagonist, with two receptor subtypes in the rabbit isolated saphenous vein. Prostaglandins, 52, 125-139.
27. 2. Mol. Pharmacol., 60, 36-41.
28. 4 receptors expressed with semliki forest virus. Br. J. Pharmacol., 121, 1673-1678.
29. MODY, S.M., HO, M.K.C., JOSHI, S.A. & WONG, Y.H. (2000). Incorporation of Gz-specific sequence at the carboxyl terminus increases the promiscuity of G16 toward Gi-coupled receptors. Mol. Pharmacol., 57, 13-23.
30. 4 in colon carcinogenesis. Cancer Res., 62, 28-32.
31. NARUMIYA, S., SUGIMOTO, Y. & USHIKUBI, F. (1999). Prostanoid receptors: structures, properties and functions. Phys. Rev., 19, 1193-1226.
32. 2 subtype. 11th International Conference on Advances in Prostaglandin and Leukotriene Research: Basic Science and New Clinical Applications. Florence, Italy, June 4th-8th, 2000.
33. 2 receptor agonists. WO 2005/080367 A1.
34. PALOMER, A., CABRE, F., PASCUAL, J., CAMPOS, J., TRUJILLO, M.A., ENTRENA, A., GALLO, M.A., GARCIA, L., MAULEON, D. & ESPINOSA, A. (2002). Identification of novel cyclooxygenase-2 selective inhibitors using pharmacophore models. J. Med. Chem., 45, 1402-1411.
35. 4 subtype on cytokine regulation and its related diseases, llth International Conference on Advances in Prostaglandin and Leukotriene Research: Basic Science and New Clinical Applications. Florence, Italy, June 4th-8th, 2000.
36. 2 receptor agonists, 11th International Conference on Advances in Prostaglandin and Leukotriene Research: Basic Science and New Clinical Applications. Florence, Italy, June 4th-8th, 2000.
37. TSUBOI, K., SUGIMOTO, Y. & ICHIKAWA, A. (2002). Prostanoid receptor subtypes. Prost. Other Lip. Med., 68-69, 535-556.
38. WILSON, R.J. & GILES, H. (2005). Piglet saphenous vein contains multiple relaxatory prostanoid receptors: evidence for EP4, EP2, DP & IP receptor subtypes. Br. J. Pharmacol., 144, 405-415.
39. WILSON, R.J., GIBLIN, G.M.P., FOORD, S.M., SWARBRICK, M., WALKER, A., BAMFORD, M., ROOMANS, S., MASON, A., MILLER, N., JONES, H., SHANAHAN, S., RASMUSSEN, S., SMITH, L., SPALDING, D., RANSHAW, L., FENWICK, R., ANCLIFF, R., SAEZ, V., FRYE, S., STRATTON, S., LEWELL, X., CARTWRIGHT, K.-A., K-A RHODES, S., ROBERTS, N. & GREEN, R. (2003). GW627368X: a Novel, potent and selective EP4 prostanoid receptor antagonist. Br. J. Pharmacol., 138, 84P.
40. 2 receptors. Eur. J. Pharmacol., 386, 89-96.
41. WRIGHT, D.H., METTERS, K.M., ABRAMOVITZ, M. & FORDHUTCHINSON, A.W. (1998). Characterization of the recombinant human prostanoid DP receptor and identification of L-644,698, a novel selective DP agonist. Br. J. Pharmacol., 123, 1317-1324.
42. YAMAMOTO, H., MARUYAMA, T., SAKATA, K., KOKETSU, M., KOBAYASHI, M., YOSHIDA, H., SEKI, A., TANI, K., MARUYAMA, T., KONDO, K. & OHUCHIDA, S. (1999). Novel four selective agonists for prostaglandin E receptor subtypes. Prost. Lip. Med., 59, 150.
43. 2. Biochem. Biophys. Res. Comms., 198, 999-1006.