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Key Documents

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B1401

Sigma-Aldrich

Bradykinin Fragment 1-5

≥97% (HPLC)

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About This Item

Fórmula empírica (notación de Hill):
C27H40N8O6
Número de CAS:
23815-89-6
Peso molecular:
572.66
MDL number:
MFCD00076260
UNSPSC Code:
12352200
PubChem Substance ID:
24891591
NACRES:
NA.32

Quality Level

200

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Cho Yeow Koh et al.
Thrombosis and haemostasis, 102(3), 437-453 (2009-09-01)
To obtain blood meals, haematophagous animals are armed with potent pharmacological molecules to overcome several of their hosts' response systems. Among them, a large number of exogenous anticoagulants which target the haemostatic system have been identified and characterised. Studies on
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)
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
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
L J Murphey et al.
Circulation, 102(8), 829-832 (2000-08-23)
Bradykinin is a cardioprotective peptide metabolized by the angiotensin-converting enzyme (ACE). An insertion/deletion (I/D) polymorphism in the ACE gene determines plasma ACE levels. The D allele is associated with cardiovascular disease, which may relate to enhanced angiotensin II production or
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