For research use only. Not for therapeutic Use.
Bradykinin (1-5)（Cat No.:I014272） is the primary stable metabolite derived from Bradykinin through the proteolytic activity of angiotensin-converting enzyme (ACE). ACE cleaves the peptide chain of Bradykinin, resulting in the formation of Bradykinin (1-5). This metabolite retains some biological activity and is involved in various physiological processes, including vasodilation and regulation of blood pressure.
| Catalog Number | I014272 |
| CAS Number | 23815-89-6 |
| Synonyms | Bradykinin (1-5); Arg-pro-pro-gly-phe;;L-arginyl-L-prolyl-L-prolylglycyl-L-phenylalanine |
| Molecular Formula | C27H40N8O6 |
| Purity | ≥95% |
| Target | Bradykinin Receptor |
| Solubility | Soluble in DMSO |
| Storage | -20°C |
| IUPAC Name | (2S)-2-[[2-[[(2S)-1-[(2S)-1-[(2S)-2-amino-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]amino]acetyl]amino]-3-phenylpropanoic acid |
| InChI | InChI=1S/C27H40N8O6/c28-18(9-4-12-31-27(29)30)24(38)35-14-6-11-21(35)25(39)34-13-5-10-20(34)23(37)32-16-22(36)33-19(26(40)41)15-17-7-2-1-3-8-17/h1-3,7-8,18-21H,4-6,9-16,28H2,(H,32,37)(H,33,36)(H,40,41)(H4,29,30,31)/t18-,19-,20-,21-/m0/s1 |
| InChIKey | USSUMSBPLJWFSZ-TUFLPTIASA-N |
| SMILES | C1CC(N(C1)C(=O)C2CCCN2C(=O)C(CCCN=C(N)N)N)C(=O)NCC(=O)NC(CC3=CC=CC=C3)C(=O)O |
| Reference | </br>1: Voronina L, Masson A, Kamrath M, Schubert F, Clemmer D, Baldauf C, Rizzo T. Conformations of Prolyl-Peptide Bonds in the Bradykinin 1-5 Fragment in Solution and in the Gas Phase. J Am Chem Soc. 2016 Jul 27;138(29):9224-33. doi: 10.1021/jacs.6b04550. Epub 2016 Jul 18. PubMed PMID: 27366919.</br>2: Murphey LJ, Malave HA, Petro J, Biaggioni I, Byrne DW, Vaughan DE, Luther JM, Pretorius M, Brown NJ. Bradykinin and its metabolite bradykinin 1-5 inhibit thrombin-induced platelet aggregation in humans. J Pharmacol Exp Ther. 2006 Sep;318(3):1287-92. Epub 2006 Jun 13. PubMed PMID: 16772538.</br>3: Bujak-Giżycka B, Olszanecki R, Madej J, Suski M, Gębska A, Korbut R. Metabolism of bradykinin in aorta of hypertensive rats. Acta Biochim Pol. 2011;58(2):199-202. Epub 2011 May 27. PubMed PMID: 21623416.</br>4: Nieman MT, Pagan-Ramos E, Warnock M, Krijanovski Y, Hasan AA, Schmaier AH. Mapping the interaction of bradykinin 1-5 with the exodomain of human protease activated receptor 4. FEBS Lett. 2005 Jan 3;579(1):25-9. PubMed PMID: 15620686.</br>5: Shima C, Majima M, Katori M. A stable metabolite, Arg-Pro-Pro-Gly-Phe, of bradykinin in the degradation pathway in human plasma. Jpn J Pharmacol. 1992 Oct;60(2):111-9. PubMed PMID: 1479739.</br>6: Cugno M, Salerno F, Nussberger J, Bottasso B, Lorenzano E, Agostoni A. Bradykinin in the ascitic fluid of patients with liver cirrhosis. Clin Sci (Lond). 2001 Dec;101(6):651-7. PubMed PMID: 11724653.</br>7: Sawyer HA, Marini JT, Stone EG, Ruotolo BT, Gillig KJ, Russell DH. The structure of gas-phase bradykinin fragment 1-5 (RPPGF) ions: an ion mobility spectrometry and H/D exchange ion-molecule reaction chemistry study. J Am Soc Mass Spectrom. 2005 Jun;16(6):893-905. PubMed PMID: 15878286.</br>8: Murphey LJ, Hachey DL, Vaughan DE, Brown NJ, Morrow JD. Quantification of BK1-5, the stable bradykinin plasma metabolite in humans, by a highly accurate liquid-chromatographic tandem mass spectrometric assay. Anal Biochem. 2001 May 1;292(1):87-93. PubMed PMID: 11319821.</br>9: Doggrell SA. A daughter of bradykinin that protects against septicaemia. Expert Opin Investig Drugs. 2001 Aug;10(8):1567-9. PubMed PMID: 11785456.</br>10: Murphey LJ, Gainer JV, Vaughan DE, Brown NJ. Angiotensin-converting enzyme insertion/deletion polymorphism modulates the human in vivo metabolism of bradykinin. Circulation. 2000 Aug 22;102(8):829-32. PubMed PMID: 10952948.</br>11: Hirata M, Hayashi I, Yoshimura K, Ishii K, Soma K, Ohwada T, Kakita A, Majima M. Blockade of bradykinin B(2) receptor suppresses acute pancreatitis induced by obstruction of the pancreaticobiliary duct in rats. Br J Pharmacol. 2002 Jan;135(1):29-36. PubMed PMID: 11786477; PubMed Central PMCID: PMC1573123.</br>12: Prieto AR, Ma H, Huang R, Khan G, Schwartz KA, Hage-Korban EE, Schmaier AH, Davis JM, Hasan AA, Abela GS. Thrombostatin, a bradykinin metabolite, reduces platelet activation in a model of arterial wall injury. Cardiovasc Res. 2002 Mar;53(4):984-92. PubMed PMID: 11922908.</br>13: Hasan AA, Amenta S, Schmaier AH. Bradykinin and its metabolite, Arg-Pro-Pro-Gly-Phe, are selective inhibitors of alpha-thrombin-induced platelet activation. Circulation. 1996 Aug 1;94(3):517-28. Erratum in: Circulation 1996 Oct 1;94(7):1794. PubMed PMID: 8759097.</br>14: Marmarou A, Guy M, Murphey L, Roy F, Layani L, Combal JP, Marquer C; American Brain Injury Consortium. A single dose, three-arm, placebo-controlled, phase I study of the bradykinin B2 receptor antagonist Anatibant (LF16-0687Ms) in patients with severe traumatic brain injury. J Neurotrauma. 2005 Dec;22(12):1444-55. 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The preparation and characterization of novel peptide antagonists to thrombin and factor VIIa and activation of protease-activated receptor 1. J Pharmacol Exp Ther. 2004 Nov;311(2):492-501. Epub 2004 Jun 21. PubMed PMID: 15210836.</br>19: Nieman MT, LaRusch G, Fang C, Zhou Y, Schmaier AH. Oral thrombostatin FM19 inhibits prostate cancer. Thromb Haemost. 2010 Nov;104(5):1044-8. doi: 10.1160/TH09-08-0570. Epub 2010 Sep 30. PubMed PMID: 20886199; PubMed Central PMCID: PMC3552554.</br>20: Sugimoto K, Hirata M, Majima M, Katori M, Ohwada T. Evidence for a role of kallikrein-P6nin system in patients with shock after blunt trauma. Am J Physiol. 1998 Jun;274(6 Pt 2):R1556-60. PubMed PMID: 9608008. </br> </br> |
