Comparison of the molecular interactions of two antagonists, MEN16132 or icatibant, at the human kinin B 2 receptor

British Journal of Pharmacology

Volumn 162, Issue 5, 2011, Pages 1202-1212

  Meini, S ^a   Bellucci, F ^a   Catalani, C ^a   Cucchi, P ^a   Giolitti, A ^a   Giuliani, S ^a   Quartara, L ^a   Rotondaro, L ^b   Zappitelli, S ^b   Maggi, C A ^a  

^a Menarini Ricerche ^*  (Italy)

^b Menarini Ricerche SpA   (Italy)

Author keywords

antagonist interaction; binding; bradykinin; G protein coupled receptors; icatibant; kinin B 2 receptor; MEN16132; mutagenesis; reversibility

Indexed keywords

4 AMINO 5 [4 [4 [2,4 DICHLORO 3 (2,4 DIMETHYL 8 QUINOLYLOXYMETHYL)PHENYLSULFONAMIDO]TETRAHYDRO 2H 4 PYRANYLCARBONYL]PIPERAZINO 5 OXOPENTYL] (TRIMETHYL)AMMONIUM CHLORIDE; BRADYKININ B2 RECEPTOR; BRADYKININ B2 RECEPTOR ANTAGONIST; ICATIBANT; MEN 16132; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; BINDING SITE; CONTROLLED STUDY; DRUG RECEPTOR BINDING; HUMAN; HUMAN CELL; MUTANT; NONHUMAN; POINT MUTATION; PRIORITY JOURNAL; PROTEIN STRUCTURE; WILD TYPE;

AMINO ACID SUBSTITUTION; ANIMALS; BINDING SITES; BRADYKININ; CHO CELLS; CRICETINAE; CRICETULUS; HUMANS; KINETICS; MODELS, MOLECULAR; MUTAGENESIS, SITE-DIRECTED; MUTANT PROTEINS; OLIGOPEPTIDES; ORNITHINE; PEPTIDES, CYCLIC; RECEPTOR, BRADYKININ B2; RECOMBINANT PROTEINS; SULFONAMIDES;

EID: 79551503731     PISSN: 00071188     EISSN: 14765381     Source Type: Journal    
DOI: 10.1111/j.1476-5381.2010.01133.x     Document Type: Article

References (40)

1. Alexander SPH, Mathie A, Peters JA, (2009). Guide to Receptors and Channels (GRAC). Br J Pharmacol 158: S1-S254.
2. 2 receptor. Molec Pharmacol 52: 16-20. (Pubitemid 27318613)
3. 2 receptor: evidence from mutational analysis. Br J Pharmacol 140: 500-506.
4. 2 receptor. Eur J Pharmacol 491: 121-125.
5. 2 receptor antagonism in human synovial fibroblasts. Br J Pharmacol 158: 1996-2004.
6. Bond AP, Breipohl G, Worthy K, Campion G, Dieppe PA, Bhoola KD, (1992). Metabolism and characterisation of kinins and Hoe 140 (kinin antagonist) in the synovial fluid of patients with inflammatory joint diseases. Agents Actions Suppl 38: 582-589.
7. 50) of an enzymatic reaction. Biochem Pharmacol 22: 3099-3108.
8. Cherezov V, Rosenbaum DM, Hanson MA, Rasmussen SG, Thian FS, Kobilka TS, et al. (2007). High-resolution crystal structure of an engineered human beta2-adrenergic G protein-coupled receptor. Science 318: 1258-1265.
9. 2 receptor antagonist, on nociceptive response in monosodium iodoacetate-induced experimental osteoarthritis in rats. J Pharmacol Exp Ther 331: 1025-1032.
10. Copeland RA, Pompliano DL, Meek TD, (2006). Drug-target residence time and its implications for lead optimization. Nat Rev Drug Discov 5: 730-739.
11. 2 receptor. In vitro pharmacology and molecular characterization. Eur J Pharmacol 528: 7-16.
12. Dziadulewicz EK, (2005). Non-peptide ligands for bradykinin receptors 1995-2004. Expert Opin Ther Patent 15: 829-859.
13. 2 receptor antagonists. 1. Synthesis and SAR of alpha,alpha-dimethylglycine sulfonamides. J Med Chem 49: 3602-3613.
14. 2 receptor antagonists. 2. Synthesis and structure-activity relationships of alpha,alpha-cycloalkylglycine sulfonamides. J Med Chem 50: 550-565.
15. Fincham CI, Bressan A, Paris M, Rossi C, Fattori D, (2009). Bradykinin receptor antagonists-a review of the patent literature 2005-2008. Expert Opin Ther Pat 19: 919-941.
16. Gether U, Kobilka BK, (1998). G Protein-coupled receptors. II. Mechanism of agonist activation. J Biol Chem 273: 17979-17982.
17. Hess JF, Borkowski JA, Young GS, Strader CD, Ransom RW, (1992). Cloning and pharmacological characterization of a human bradykinin (BK-2) receptor. Biochem Biophys Res Comm 184: 260-268.
18. Hock FJ, Wirth K, Albus U, Linz W, Gerhards HJ, Wiemer G, et al. (1991). Hoe 140 a new potent and long acting bradykinin-antagonist: in vitro studies. Br J Pharmacol 102: 769-773.
19. 2 bradykinin receptor reveal a different pattern of contacts for peptidic agonists and peptidic antagonists. J Biol Chem 271: 28277-28286.
20. Kenakin TP, (1997). Competitive antagonism. In:, Kenakin TP, (ed.). Pharmacologic Analysis of Drug-Receptor Interaction, 3rd edn. Lippincott Williams & Wilkins: Philadelphia, PA, pp. 331-373.
21. Kyle DJ, (1995). Structure-based drug design: progress toward the discovery of the elusive bradykinin receptor antagonists. Curr Pharm Design 1: 233-254.
22. Leeb-Lundberg LM, Marceau F, Muller-Esterl W, Pettibone DJ, Zuraw BL, (2005). International union of pharmacology. XLV. Classification of the kinin receptor family: from molecular mechanisms to pathophysiological consequences. Pharmacol Rev 57: 27-77.
23. Legat FJ, Griesbacher T, Lembeck F, (1994). Mediation by bradykinin of rat paw oedema induced by collagenase from Clostridium histolyticum. Br J Pharmacol 112: 453-460.
24. 2 bradykinin receptor. J Biol Chem 276: 41100-41111.
25. 2 kinin receptor. J Pharmacol Exp Ther 289: 1250-1256.
26. 2 receptor for nonpeptide antagonist ligands recognition. Can J Physiol Pharmacol 80: 303-309.
27. 2 receptor and molecular modelling to define the pharmacophore of non-peptide bradykinin receptor antagonists. Biochem Pharmacol 67: 601-609.
28. 2 receptor: radioligand binding and smooth muscle contractility studies. Br J Pharmacol 150: 313-320.
29. 2 receptor antagonist MEN16132 in rat in vitro bioassays. Eur J Pharmacol 615: 10-16.
30. 2 receptor in the rabbit and pig ileal smooth muscle. Eur J Pharmacol 635: 34-39.
31. 2 bradykinin receptor decrease affinity for bradykinin. Biochem Biophys Res Commun 201: 523-530.
32. Palczewski K, Kumasaka T, Hori T, Behnke CA, Motoshima H, Fox BA, et al. (2000). Crystal structure of rhodopsin: A G protein-coupled receptor. Science 289: 739-745.
33. Rasmussen SG, Choi HJ, Rosenbaum DM, Kobilka TS, Thian FS, Edwards PC, et al. (2007). Crystal structure of the human beta2 adrenergic G-protein-coupled receptor. Nature 450: 383-387.
34. Regoli D, Barabé J, (1980). Pharmacology of bradykinin and related kinins. Pharmacol Rev 32: 1-46.
35. Rosenbaum DM, Cherezov V, Hanson MA, Rasmussen SG, Thian FS, Kobilka TS, et al. (2007). GPCR engineering yields high-resolution structural insights into beta2-adrenergic receptor function. Science 318: 1266-1273.
36. Rosenbaum DM, Rasmussen SG, Kobilka BK, (2009). The structure and function of G-protein-coupled receptors. Nature 459: 356-363.
37. 2 receptor antagonist: in vivo activity on bradykinin-induced bronchoconstriction and nasal mucosa microvascular leakage in anesthetized guinea pigs. J Pharmacol Exp Ther 315: 616-623.
38. 2 receptor antagonist, prevents the endogenous bradykinin effects in guinea-pig airways. Eur J Pharmacol 579: 350-356.
39. Vauquelin G, Van Liefde I, (2006). Slow antagonist dissociation and long-lasting in vivo receptor protection. Trends Pharmacol Sci 27: 355-359.
40. Wirth K, Hock FJ, Albus U, Linz W, Alpermann HG, Anagnostopoulos H, et al. (1991). Hoe 140 a new potent and long acting bradykinin-antagonist: in vivo studies. Br J Pharmacol 102: 774-777.