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B1401

Sigma-Aldrich

Bradykinin Fragment 1-5

≥97% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C27H40N8O6
CAS Number:
23815-89-6
Molecular Weight:
572.66
MDL number:
MFCD00076260
UNSPSC Code:
12352200
PubChem Substance ID:
24891591
NACRES:
NA.32

Assay

≥97% (HPLC)

form

powder

UniProt accession no.

P01042

storage temp.

−20°C

SMILES string

NC(CCCNC(N)=N)C(=O)N1CCCC1C(=O)N2CCCC2C(=O)NCC(=O)NC(Cc3ccccc3)C(O)=O

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)

InChI key

USSUMSBPLJWFSZ-UHFFFAOYSA-N

Gene Information

human ... KNG1 (includes EG:3827)

Amino Acid Sequence

Arg-Pro-Pro-Gly-Phe

Biochem/physiol Actions

The bradykinin (BK) fragment (1-5) (RPPGF) is among the most stable of naturally occurring metabolites. It may be used as a marker for BK production in vivo. It is known that an intact Arg residue in the C-terminus is required for biological activities. BK 1-5 is the minimal peptide that inhibited α-thrombin-induced platelet aggregation and secretion and calcium mobilization. It also prevented α-thrombin from cleaving the thrombin receptor peptide, NATLDPRSFLLR, between arginine and serine. Such antithrombin activities of BK 1-5 may contribute to the cardioprotective nature of kinins.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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T A Morinelli et al.
The Journal of pharmacology and experimental therapeutics, 296(1), 71-76 (2000-12-21)
Extensive research has provided few therapeutic agents for the treatment of septicemia. Bradykinin, an endogenous vasodepressor hormone, is a key mediator in the hypotension seen with septicemia. The present investigation shows that a stable metabolic fragment of bradykinin, arginine-proline-proline-glycine-phenylalanine (RPPGF)
Marvin T Nieman et al.
The Journal of pharmacology and experimental therapeutics, 311(2), 492-501 (2004-06-24)
Thrombin and protease-activated receptor 1 (PAR1) activation antagonists were prepared based upon the peptide RPPGF, the angiotensin-converting enzyme breakdown product of bradykinin. A library of 72 peptides consisting of d and/or synthetic amino acids was designed with various substitutions in
A A Hasan et al.
Thrombosis and haemostasis, 82(3), 1182-1187 (1999-09-24)
Thrombostatin (RPPGF), an angiotensin converting enzyme metabolite of bradykinin, is an inhibitor of alpha-thrombin's ability to activate platelets. We examined the in vivo pharmacokinetics and pharmacodynamics of thrombostatin in rabbits and its ability to inhibit coronary thrombosis induced by electrolytic
M T Nieman et al.
Journal of thrombosis and haemostasis : JTH, 6(5), 837-845 (2008-03-05)
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 bradykinin - RPPGF. These peptides are direct thrombin inhibitors prolonging the thrombin clotting time
Mias Pretorius et al.
Arteriosclerosis, thrombosis, and vascular biology, 25(11), 2435-2440 (2005-09-17)
Angiotensin-converting enzyme inhibition (ACEI) increases vascular tissue plasminogen activator (t-PA) release through endogenous bradykinin (BK). We tested the hypothesis that gender influences the effect of ACEI on t-PA release. We measured the effect of intra-arterial enalaprilat (0.33 microg/min per 100
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