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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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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Harald Eisenbarth et al.
Pain, 110(1-2), 197-204 (2004-07-28)
Bradykinin B1 and B2 receptors contribute to nociceptor sensitization under inflammatory conditions. Here, we examined the vascular inflammatory responses and nociceptive effects resulting from activation of B1 and B2 receptors in healthy and UV-B irradiated skin in human volunteers. The
Edson L Santos et al.
International immunopharmacology, 8(2), 282-288 (2008-01-10)
In the kallikrein-kinin and renin-angiotensin systems the main receptors, B1 and B2 (kinin receptors) and AT1 and AT2 (angiotensin receptors) respectively, are seven-transmembrane domain G-protein-coupled receptors. Considering that the B1 agonists Des-Arg9-BK (Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe), Lys-desArg9-BK or Des-Arg10-KD (Lys-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe) and the AT1
Richard W Ransom et al.
European journal of pharmacology, 499(1-2), 77-84 (2004-09-15)
Compound A (N-[2-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]ethyl]-2-[(2R)-1-(2-napthylsulfonyl)-3-oxo-1,2,3,4-tetrahydroquinoxalin-2-yl]acetamide) is a member of a new class of aryl sulfonamide dihydroquinoxalinone bradykinin B1 receptor antagonists that should be useful pharmacological tools. Here we report on some of the pharmacological properties of compound A as well as the
J A Santiago et al.
The American journal of physiology, 269(6 Pt 2), H2057-H2064 (1995-12-01)
Responses to kallidin, des-Arg9-bradykinin (DABK), and des-Arg10-kallidin (DAK) were investigated in the hindlimb vascular bed of the cat under constant-flow conditions. Injections of kallidin, DABK, and DAK into the hindlimb perfusion circuit produced dose-dependent vasodilator responses in the hindlimb vascular
Jon E Hawkinson et al.
The Journal of pharmacology and experimental therapeutics, 322(2), 619-630 (2007-05-02)
The bradykinin B(1) receptor plays a critical role in chronic pain and inflammation, although efforts to demonstrate efficacy of receptor antagonists have been hampered by species-dependent potency differences, metabolic instability, and low oral exposure of current agents. The pharmacology, pharmacokinetics
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