A metabolite of bradykinin
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Bradykinin Fragment (1-5) (trifluoroacetate salt)

Item No. 35302

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Synonyms
  • Arg-Pro-Pro-Gly-Phe
  • BK Fragment 1-5
  • RPPGF
Molecular Formula
C27H40N8O6 • XCF3COOH
Formula Weight
572.7
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlEthanol: 3 mg/mlPBS (pH 7.2): 5 mg/ml
SMILES
N=C(N)NCCC[C@H](N)C(N1[C@H](C(N2[C@H](C(NCC(N[C@@H](CC3=CC=CC=C3)C(O)=O)=O)=O)CCC2)=O)CCC1)=O.OC(C(F)(F)F)=O
InChi Code
InChI=1S/C27H40N8O6.C2HF3O2/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;3-2(4,5)1(6)7/h1-3,7-8,18-21H,4-6,9-16,28H2,(H,32,37)(H,33,36)(H,40,41)(H4,29,30,31);(H,6,7)/t18-,19-,20-,21-;/m0./s1
InChi Key
LAPYOHFGOBOFAC-NCEXEODOSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    10 mg

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    Cayman Chemical
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    Product Description

    Bradykinin fragment (1-5) is a metabolite of the endogenous vasodilator bradykinin (Item No. 37408).1 It is formed from bradykinin by angiotensin-converting enzyme (ACE). Bradykinin fragment (1-5) (100 nM) increases the production of nitric oxide (NO) in neonatal rat cardiomyocytes.2 It inhibits α-thrombin-induced platelet aggregation of washed isolated platelets (IC50 = 0.5 mM).3 Bradykinin fragment (1-5) prevents decreases in mean arterial blood pressure and heart rate and increases survival in a rat model of LPS-induced septicemia.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bujak-Giżycka, B., Olszanecki, R., Madej, J., et al. Metabolism of bradykinin in aorta of hypertensive rats. Acta Biochim. Pol. 58(2), 199-202 (2011).

    2. Souza-Silva, I.M., de Paula, C.A., Bolais-Amos, L., et al. Peptide fragments of bradykinin show unexpected biological activity not mediated by B1 or B2 receptors. Br. J. Pharmacol. 179(12), 3061-3077 (2022).

    3. Hasan, A.A.K., Amenta, S., and Schmaier, A.H. Bradykinin and its metabolite, Arg-Pro-Pro-Gly-Phe, are selective inhibitors of α-thrombin-induced platelet activation. Circulation 94(3), 517-528 (1996).

    4. Morinelli, T.A., Webb, J.G., Jaffa, A.A., et al. A metabolic fragment of bradykinin, Arg-Pro-Pro-Gly-Phe, protects against the deleterious effects of lipopolysaccharide in rats. J. Pharmacol. Exp. Ther. 296(1), 71-76 (2001).