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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
Wanda Nowak et al.
Naunyn-Schmiedeberg's archives of pharmacology, 375(3), 221-229 (2007-03-21)
It has been known for many years that plasma and tissues contain a variety of enzymes capable of metabolizing kinins. The aim of the present study was to evaluate, by means of functional studies in a capacitance vessel such as
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
J P Galizzi et al.
British journal of pharmacology, 113(2), 389-394 (1994-10-01)
1. Binding of the specific bradykinin B1 receptor agonist, [3H]-des-Arg10-kallidin (-KD) was investigated in smooth muscle cells (SMC) isolated from rabbit mesenteric arteries (RMA). 2. [3H]-des-Arg10-KD specifically bound to interleukin-1 (IL-1)-treated RMA-SMC in a saturable fashion with an equilibrium dissociation
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
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