Bradykinin Fragment 1-5

Names

[ Name ]:
Bradykinin Fragment 1-5

[Synonym ]:
Arg-pro-pro-gly-phe
Bradykinin Fragment-1-5
2-[2-({1-[1-(2-amino-5-carbamimidamidopentanoyl)pyrrolidine-2-carbonyl]pyrrolidin-2-yl}formamido)acetamido]-3-phenylpropanoic acid
Bradykinin: 1-5
Bradykinin (1-5)

Biological Activity

[Description]:

Bradykinin (1-5) is a major stable metabolite of Bradykinin, formed by the proteolytic action of angiotensin-converting enzyme (ACE).

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Bradykinin Receptor

Peptides

Research Areas >> Cardiovascular Disease

[In Vivo]

Bradykinin is a short-lived vasoactive peptide, with a reported half-life in vivo of 17 s, that is rapidly metabolized in the circulation to Bradykinin (1-5). Bradykinin (1-5), the product of two sequential cleavages of Bradykinin by ACE at the Pro7-Phe8 and Phe5-Ser6bonds, has been identified as the major stable metabolite of Bradykinin in vivo in human subjects, with a terminal half-life of minutes. Both Bradykinin and Bradykinin (1-5) inhibit α- and γ-thrombin-induced platelet aggregation (P<0.01 versus baseline). Bradykinin (1-5) inhibits γ-thrombin-induced platelet aggregation 50% at a calculated dose of 183±3 pmol/min. Neither Bradykinin nor Bradykinin (1-5) affects thrombin receptor-activating peptide-induced platelet aggregation, consistent with the hypothesis that Bradykinin and Bradykinin 1-5 inhibit thrombin-induced platelet aggregation by preventing cleavage of the thrombin receptor and liberation of thrombin receptor-activating peptide. Bradykinin (1-5) significantly attenuates α-thrombin-induced platelet aggregation but not TRAP 1-6-induced platelet aggregation. Bradykinin (1-5) potently inhibits γ-thrombin (500 nM)-induced platelet aggregation with an ED50 of 183±2 pmol/min[1].

[References]

[1]. Murphey LJ, et al. Bradykinin and its metabolite Bradykinin 1-5 inhibit thrombin-induced platelet aggregation in humans. J Pharmacol Exp Ther. 2006 Sep;318(3):1287-92.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.46g/cm3

[ Molecular Formula ]:
C₂₇H₄₀N₈O₆

[ Molecular Weight ]:
572.65600

[ Exact Mass ]:
572.30700

[ PSA ]:
224.04000

[ LogP ]:
1.03610

[ Index of Refraction ]:
1.677

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
F+

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3.0

Articles

Angiotensin-converting enzyme inhibition and smoking potentiate the kinin response to cardiopulmonary bypass.

Clin. Pharmacol. Ther. 76(4) , 379-87, (2004)

This study tested the hypothesis that angiotensin-converting enzyme (ACE) inhibitors potentiate activation of the kallikrein-kinin system during cardiopulmonary bypass (CPB).The effects of CPB on conc...

Thrombostatin inhibits cyclic flow variations in stenosed canine coronary arteries.

Thromb. Haemost. 86(5) , 1296-304, (2001)

Thrombostatins are a group of compounds based upon a breakdown product of bradykinin, RPPGF. They inhibit alpha-thrombin-induced platelet activation by binding to protease activated receptor 1 and, at...

Thrombostatin FM compounds: direct thrombin inhibitors - mechanism of action in vitro and in vivo.

J. Thromb. Haemost. 6(5) , 837-45, (2008)

Novel pentapeptides called Thrombostatin FM compounds consisting mostly of D-isomers and unusual amino acids were prepared based upon the stable angiotensin converting enzyme breakdown product of brad...