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B1542

Sigma-Aldrich

[Lys-des-Arg9]-Bradykinin

≥95% (HPLC)

Synonym(s):

des-Arg10-Kallidin

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About This Item

Empirical Formula (Hill Notation):
C50H73N13O11
CAS Number:
71800-36-7
Molecular Weight:
1032.20
MDL number:
MFCD00079826
UNSPSC Code:
12352209
PubChem Substance ID:
329773191
NACRES:
NA.32

Quality Level

200

Assay

≥95% (HPLC)

form

powder

UniProt accession no.

P01042

storage temp.

−20°C

SMILES string

NCCCC[C@H](N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1CCC[C@H]1C(=O)N2CCC[C@H]2C(=O)NCC(=O)N[C@@H](Cc3ccccc3)C(=O)N[C@@H](CO)C(=O)N4CCC[C@H]4C(=O)N[C@@H](Cc5ccccc5)C(O)=O

InChI

1S/C50H73N13O11/c51-22-8-7-17-33(52)42(66)58-34(18-9-23-55-50(53)54)46(70)63-26-12-21-40(63)48(72)62-25-10-19-38(62)44(68)56-29-41(65)57-35(27-31-13-3-1-4-14-31)43(67)60-37(30-64)47(71)61-24-11-20-39(61)45(69)59-36(49(73)74)28-32-15-5-2-6-16-32/h1-6,13-16,33-40,64H,7-12,17-30,51-52H2,(H,56,68)(H,57,65)(H,58,66)(H,59,69)(H,60,67)(H,73,74)(H4,53,54,55)/t33-,34-,35-,36-,37-,38-,39-,40-/m0/s1

InChI key

AILVBOHFGXNHCC-TZPCGENMSA-N

Gene Information

human ... KNG1 (includes EG:3827)

Amino Acid Sequence

Lys-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe

Application

[Lys-des-Arg9]-Bradykinin has been used as a B1R agonist to investigate the role of B1R in diabetes-induced secondary hemorrhage.

Biochem/physiol Actions

[Des-Arg10]-kallidin or [Lys-des-Arg9]-Bradykinin is a bradykinin B1 receptor agonist. It strongly upregulates the B1 receptor and is blocked by a specific protein kinase C inhibitor. The upregulation is correlated with the induction of transcription nuclear factor κB (NF-κB). Elevation of Lys-des[Arg9]–bradykinin because of airway inflammation in asthma patients is known to modify the immune responses. It affects the migration and production of interleukin-12 in monocyte-derived dendritic cells.

Other Notes

Lyophilized from 0.1% TFA in H2O

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)

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J P Schanstra et al.
The Journal of clinical investigation, 101(10), 2080-2091 (1998-05-29)
The bradykinin B1-receptor is strongly upregulated under chronic inflammatory conditions. However, the mechanism and reason are not known. Because a better understanding of the mechanism of the upregulation will help in understanding its potential importance in inflammation, we have studied
Oleg Zaika et al.
American journal of physiology. Renal physiology, 300(5), F1105-F1115 (2011-02-18)
Activation of the renal kallikrein-kinin system results in natriuresis and diuresis, suggesting its possible role in renal tubular sodium transport regulation. Here, we used patch-clamp electrophysiology to directly assess the effects of bradykinin (BK) on the epithelial Na(+) channel (ENaC)
Ninian N Lang et al.
Journal of cardiovascular pharmacology, 52(5), 438-444 (2008-11-27)
Animal models suggest a vasomotor role for the B1 kinin receptor in cardiovascular disease states. In patients with heart failure treated with angiotensin-converting enzyme inhibition (ACEi), or combined B1/B2 receptor antagonism, but not B2 receptor antagonism alone, causes vasoconstriction. However
Nicholas L M Cruden et al.
Heart and vessels, 27(2), 179-185 (2011-03-12)
Upregulation of vascular B(1) kinin receptor expression has been reported in human atheroma, but its role remains unclear. We examined vasomotor and fibrinolytic responses to selective B(1) and B(2) kinin receptor agonism in the human femoral circulation and correlated responses
F Bellucci et al.
British journal of pharmacology, 150(2), 192-199 (2006-12-21)
Kinins have an important role in inflammatory cystitis and in animal pathophysiological models, by acting on epithelium, fibroblasts, sensory innervation and smooth muscle. The aim of this study was to characterize the receptors responsible for direct motor responses induced by
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