Structure-activity relationships of novel peptide agonists of the human bradykinin B2 receptor

Peptides

Volumn 30, Issue 4, 2009, Pages 777-787

  Bélanger, Simon ^a   Bovenzi, Veronica ^a   Côté, Jérome ^a   Neugebauer, Witold ^a   Amblard, Muriel ^b   Martinez, Jean ^b   Lammek, Bernard ^c   Savard, Martin ^a   Gobeil Jr , Fernand ^a  

^a UNIVERSITÉ DE SHERBROOKE   (Canada)

^b UNIV MONTPELLIER   (France)

^c UNIVERSITY OF GDA SK   (Poland)

Author keywords

Bioassays; Bradykinin; GPCR; Human; Peptide agonists

Indexed keywords

BRADYKININ B2 RECEPTOR;

ANIMAL EXPERIMENT; ARTICLE; CELL STRAIN HEK293; CONTROLLED STUDY; HUMAN; HUMAN CELL; IN VITRO STUDY; MALE; NONHUMAN; PRIORITY JOURNAL; PROTEIN DEGRADATION; PROTEIN STRUCTURE; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION;

ANIMALS; BLOOD PRESSURE; BLOTTING, WESTERN; BRADYKININ; CELL LINE; HUMANS; MALE; PEPTIDES; PHOSPHORYLATION; RABBITS; RATS; RATS, SPRAGUE-DAWLEY; RECEPTOR, BRADYKININ B2; REVERSE TRANSCRIPTASE POLYMERASE CHAIN REACTION; STRUCTURE-ACTIVITY RELATIONSHIP;

ORYCTOLAGUS CUNICULUS; RATTUS;

EID: 62749205749     PISSN: 01969781     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.peptides.2008.12.003     Document Type: Article

References (64)

1. IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). Nomenclature and symbolism for amino acids and peptides. Recommendations 1983. Eur J Biochem 138 (1984) 9-37
2. Amblard M., Daffix I., Bedos P., Berge G., Pruneau D., Paquet J.L., et al. Design and synthesis of potent bradykinin agonists containing a benzothiazepine moiety. J Med Chem 42 (1999) 4185-4192
3. Aramori I., Zenkoh J., Morikawa N., Asano M., Hatori C., Sawai H., et al. Nonpeptide mimic of bradykinin with long-acting properties at the bradykinin B2 receptor. Mol Pharmacol 52 (1997) 16-20
4. Aramori I., Zenkoh J., Morikawa N., O'Donnell N., Asano M., Nakamura K., et al. Novel subtype-selective nonpeptide bradykinin receptor antagonists FR167344 and FR173657. Mol Pharmacol 51 (1997) 171-176
5. Bawolak M.T., Gera L., Morissette G., Stewart J.M., and Marceau F. B-9972 (d-Arg-[Hyp3,Igl5,Oic7,Igl8]-bradykinin) is an inactivation-resistant agonist of the bradykinin B2 receptor derived from the peptide antagonist B-9430 (d-Arg-[Hyp3,Igl5,d-Igl7,Oic8]-bradykinin): pharmacologic profile and effective induction of receptor degradation. J Pharmacol Exp Ther 323 (2007) 534-546
6. Bhoola K.D., Figueroa C.D., and Worthy K. Bioregulation of kinins: kallikreins, kininogens, and kininases. Pharmacol Rev 44 (1992) 1-80
7. Blaukat A., Herzer K., Schroeder C., Bachmann M., Nash N., and Muller-Esterl W. Overexpression and functional characterization of kinin receptors reveal subtype-specific phosphorylation. Biochemistry 38 (1999) 1300-1309
8. Boels K., and Schaller H.C. Identification and characterisation of GPR100 as a novel human G-protein-coupled bradykinin receptor. Br J Pharmacol 140 (2003) 932-938
9. Boix F., Rosenborg L., Hilgenfeldt U., and Knardahl S. Contraction-related factors affect the concentration of a kallidin-like peptide in rat muscle tissue. J Physiol 544 (2002) 127-136
10. Chao J., and Chao L. Kallikrein-kinin in stroke, cardiovascular and renal disease. Exp Physiol 90 (2005) 291-298
11. Couture R., and Girolami J.P. Putative roles of kinin receptors in the therapeutic effects of angiotensin 1-converting enzyme inhibitors in diabetes mellitus. Eur J Pharmacol 500 (2004) 467-485
12. Cruden N.L., and Newby D.E. Clots, kinins and coronaries. Atherosclerosis 183 (2005) 189-198
13. D'Orleans-Juste P., Sirois M.G., Edelman E.R., Regoli D., Pheng L.H., Bkaily G., et al. DNA antisense strategies in the study of receptors for vasoactive peptides, and of growth and wound-healing factors. Mol Cell Biochem 172 (1997) 199-211
14. Dendorfer A., Wagemann M., Reissmann S., and Dominiak P. Structural requirements for B2-agonists with improved degradation stability. Immunopharmacology 45 (1999) 199-205
15. Doctrow S.R., Abelleira S.M., Curry L.A., Heller-Harrison R., Kozarich J.W., Malfroy B., et al. The bradykinin analog RMP-7 increases intracellular free calcium levels in rat brain microvascular endothelial cells. J Pharmacol Exp Ther 271 (1994) 229-237
16. Drapeau G., Audet R., Levesque L., Godin D., and Marceau F. Development and in vivo evaluation of metabolically resistant antagonists of B1 receptors for kinins. J Pharmacol Exp Ther 266 (1993) 192-199
17. Drapeau G., Rhaleb N.E., Dion S., Jukic D., and Regoli D. [Phe8 psi(CH2-NH)Arg9]bradykinin, a B2 receptor selective agonist which is not broken down by either kininase I or kininase II. Eur J Pharmacol 155 (1988) 193-195
18. Dunn F.W., and Stewart J.M. Analogs of bradykinin containing -2-thienyl-l-alanine. J Med Chem 14 (1971) 779-781
19. Erdös E., and Skidgel R. The kinin system. In: Farmer S. (Ed). The handbook of immunopharmacology systems (1997), Academic Press, San Diego 111-142
20. Erlich Y., Mayk A., and Rosenthal T. Nitric oxide does not participate in the metabolic effects of exogenous bradykinin in fructose-fed rats. Am J Hypertens 14 (2001) 3-6
21. Gessi S., Rizzi A., Calo G., Agnello G., Jorizzo G., Mollica G., et al. Human vascular kinin receptors of the B2 type characterized by radioligand binding. Br J Pharmacol 122 (1997) 1450-1454
22. Gobeil F., Filteau C., Pheng L.H., Jukic D., Nguyen-Le X.K., and Regoli D. In vitro and in vivo characterization of bradykinin B2 receptors in the rabbit and the guinea pig. Can J Physiol Pharmacol 74 (1996) 137-144
23. Gobeil Jr. F., Charland S., Filteau C., Perron S.I., Neugebauer W., and Regoli D. Kinin B1 receptor antagonists containing alpha-methyl-l-phenylalanine: in vitro and in vivo antagonistic activities. Hypertension 33 (1999) 823-829
24. Gobeil Jr. F., Halle S., Blais P.A., and Regoli D. Studies on the angiotensin-converting enzyme and the kinin B2 receptor in the rabbit jugular vein: modulation of contractile response to bradykinin. Can J Physiol Pharmacol 80 (2002) 153-163
25. Gobeil Jr. F., Montagne M., Inamura N., and Regoli D. Characterization of non-peptide bradykinin B2 receptor agonist (FR 190997) and antagonist (FR 173657). Immunopharmacology 43 (1999) 179-185
26. Gobeil F., Neugebauer W., Nguyen-Le X.K., Nea Allogho S., Pheng L.H., Blouin D., et al. Pharmacological profiles of the human and rabbit B1 receptors. Can J Physiol Pharmacol 75 (1997) 591-595
27. Gobeil F., Pheng L.H., Badini I., Nguyen-Le X.K., Pizard A., Rizzi A., et al. Receptors for kinins in the human isolated umbilical vein. Br J Pharmacol 118 (1996) 289-294
28. Gougat J., Ferrari B., Sarran L., Planchenault C., Poncelet M., Maruani J., et al. SSR240612 [(2R)-2-[((3R)-3-(1,3-benzodioxol-5-yl)-3-[[(6-methoxy-2-naphthyl)sulfonyl]amino]propanoyl) amino]-3-(4-[[2R,6S)-2,6-dimethylpiperidinyl]methyl]pheny l)-N-isopropyl-N-methylpropanamide hydrochloride], a new nonpeptide antagonist of the bradykinin B1 receptor: biochemical and pharmacological characterization. J Pharmacol Exp Ther 309 (2004) 661-669
29. Griesbacher T. Kallikrein-kinin system in acute pancreatitis: potential of B(2)-bradykinin antagonists and kallikrein inhibitors. Pharmacology 60 (2000) 113-120
30. Hall J., and Morton K. The kinin system. In: Farmer S. (Ed). The handbook of immunopharmacology systems (1997), Academic Press, San Diego 9-43
31. Heitsch H. The therapeutic potential of bradykinin B2 receptor agonists in the treatment of cardiovascular disease. Expert Opin Invest Drugs 12 (2003) 759-770
32. Hess J., Porte D., Munz C., and Angel P. AP-1 and Cbfa/runt physically interact and regulate parathyroid hormone-dependent MMP13 expression in osteoblasts through a new osteoblast-specific element 2/AP-1 composite element. J Biol Chem 276 (2001) 20029-20038
33. Hess J.F., Chen R.Z., Hey P., Breese R., Chang R.S., Chen T.B., et al. Generation and characterization of a humanized bradykinin B1 receptor mouse. Biol Chem 387 (2006) 195-201
34. Jenkinson D.H., Barnard E.A., Hoyer D., Humphrey P.P., Leff P., and Shankley N.P. International Union of Pharmacology Committee on Receptor Nomenclature and Drug Classification. IX. Recommendations on terms and symbols in quantitative pharmacology. Pharmacol Rev 47 (1995) 255-266
35. Kakoki M., Takahashi N., Jennette J.C., and Smithies O. Diabetic nephropathy is markedly enhanced in mice lacking the bradykinin B2 receptor. Proc Natl Acad Sci USA 101 (2004) 13302-13305
36. Kenakin T. The classification of seven transmembrane receptors in recombinant expression systems. Pharmacol Rev 48 (1996) 413-463
37. Kotovych G., Cann J.R., Stewart J.M., and Yamamoto H. NMR and CD conformational studies of bradykinin and its agonists and antagonists: application to receptor binding. Biochem Cell Biol 76 (1998) 257-266
38. Lamontagne D., Nakhostine N., Couture R., and Nadeau R. Mechanisms of kinin B1-receptor-induced hypotension in the anesthetized dog. J Cardiovasc Pharmacol 28 (1996) 645-650
39. Leeb-Lundberg L.M., Marceau F., Muller-Esterl W., Pettibone D.J., and Zuraw B.L. International union of pharmacology. XLV. Classification of the kinin receptor family: from molecular mechanisms to pathophysiological consequences. Pharmacol Rev 57 (2005) 27-77
40. Linz W., Wiemer G., Gohlke P., Unger T., and Scholkens B.A. Contribution of kinins to the cardiovascular actions of angiotensin-converting enzyme inhibitors. Pharmacol Rev 47 (1995) 25-49
41. Madeddu P., Emanueli C., and El-Dahr S. Mechanisms of disease: the tissue kallikrein-kinin system in hypertension and vascular remodeling. Nat Clin Pract Nephrol 3 (2007) 208-221
42. Majima M., Hayashi I., Inamura N., Fujita T., and Ogino M. A nonpeptide mimic of bradykinin blunts the development of hypertension in young spontaneously hypertensive rats. Hypertension 35 (2000) 437-442
43. Marceau F. Kinin B1 receptors: a review. Immunopharmacology 30 (1995) 1-26
44. Marceau F., and Regoli D. Bradykinin receptor ligands: therapeutic perspectives. Nat Rev Drug Discov 3 (2004) 845-852
45. Meini S., Bellucci F., Cucchi P., Giuliani S., Quartara L., Giolitti A., et al. Bradykinin B2 and GPR100 receptors: a paradigm for receptor signal transduction pharmacology. Br J Pharmacol 143 (2004) 938-941
46. Murphey L.J., Malave H.A., Petro J., Biaggioni I., Byrne D.W., Vaughan D.E., et al. Bradykinin and its metabolite bradykinin 1-5 inhibit thrombin-induced platelet aggregation in humans. J Pharmacol Exp Ther 318 (2006) 1287-1292
47. Nakhostine N., Ribuot C., Lamontagne D., Nadeau R., and Couture R. Mediation by B1 and B2 receptors of vasodepressor responses to intravenously administered kinins in anaesthetized dogs. Br J Pharmacol 110 (1993) 71-76
48. Naraba H., Ueno A., Kosugi Y., Yoshimura M., Murakami M., Kudo I., et al. Agonist stimulation of B1 and B2 kinin receptors causes activation of the MAP kinase signaling pathway, resulting in the translocation of AP-1 in HEK 293 cells. FEBS Lett 435 (1998) 96-100
49. Nsa Allogho S., Gobeil F., Perron S.I., Hess J.F., and Regoli D. Effects of kinins on isolated stomachs of control and transgenic knockout B2 receptor mice. Naunyn Schmiedebergs Arch Pharmacol 357 (1998) 191-196
50. Parratt J.R. Protection of the heart by ischaemic preconditioning: mechanisms and possibilities for pharmacological exploitation. Trends Pharmacol Sci 15 (1994) 19-25
51. Regoli D., and Barabe J. Pharmacology of bradykinin and related kinins. Pharmacol Rev 32 (1980) 1-46
52. Regoli D., Gobeil F., Nguyen Q.T., Jukic D., Seoane P.R., Salvino J.M., et al. Bradykinin receptor types and B2 subtypes. Life Sci 55 (1994) 735-749
53. Regoli D., Jukic D., Gobeil F., and Rhaleb N.E. Receptors for bradykinin and related kinins: a critical analysis. Can J Physiol Pharmacol 71 (1993) 556-567
54. Reissmann S., Schwuchow C., Seyfarth L., Pineda De Castro L.F., Liebmann C., Paegelow I., et al. Highly selective bradykinin agonists and antagonists with replacement of proline residues by N-methyl-d- and l-phenylalanine. J Med Chem 39 (1996) 929-936
55. Rhaleb N.E., Drapeau G., Dion S., Jukic D., Rouissi N., and Regoli D. Structure-activity studies on bradykinin and related peptides: agonists. Br J Pharmacol 99 (1990) 445-448
56. Rizzi A., Gobeil F., Calo G., Inamura N., and Regoli D. FR 173657: a new, potent, nonpeptide kinin B2 receptor antagonist. An in vitro study. Hypertension 29 (1997) 951-956
57. Sardi S.P., Daray F.M., Errasti A.E., Pelorosso F.G., Pujol-Lereis V.A., Rey-Ares V., et al. Further pharmacological characterization of bradykinin B1 receptor up-regulation in human umbilical vein. J Pharmacol Exp Ther 290 (1999) 1019-1025
58. Sharma J.N., and Thani R.B. Therapeutic prospects for bradykinin receptor agonists in the treatment of cardiovascular diseases. IDrugs 7 (2004) 926-934
59. Stewart J.M., Gera L., Chan D.C., Whalley E.T., Hanson W.L., and Zuzack J.S. Potent, long-acting bradykinin antagonists for a wide range of applications. Can J Physiol Pharmacol 75 (1997) 719-724
60. Wang D.Z., Chao L., and Chao J. Hypotension in transgenic mice overexpressing human bradykinin B2 receptor. Hypertension 29 (1997) 488-493
61. Wang X., Wei M., Kuukasjarvi P., Laurikka J., Rinne T., Moilanen E., et al. The anti-inflammatory effect of bradykinin preconditioning in coronary artery bypass grafting (bradykinin and preconditioning). Scand Cardiovasc J (2008) 1-8
62. Wilson S.R., Boix F., Holm A., Molander P., Lundanes E., and Greibrokk T. Determination of bradykinin and arg-bradykinin in rat muscle tissue by microdialysis and capillary column-switching liquid chromatography with mass spectrometric detection. J Sep Sci 28 (2005) 1751-1758
63. Wolf W.C., Yoshida H., Agata J., Chao L., and Chao J. Human tissue kallikrein gene delivery attenuates hypertension, renal injury, and cardiac remodeling in chronic renal failure. Kidney Int 58 (2000) 730-739
64. Yao Y.Y., Yin H., Shen B., Chao L., and Chao J. Tissue kallikrein and kinin infusion rescues failing myocardium after myocardial infarction. J Card Fail 13 (2007) 588-596