Bradykinin 2-9
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Bradykinin 2-9

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Bradykinin 2-9, a metabolite of Bradykinin, is an amino-truncated Bradykinin peptide cleaved by Aminopeptidase P.

Category
Peptide Inhibitors
Catalog number
BAT-010455
CAS number
16875-11-9
Molecular Formula
C44H61N11O10
Molecular Weight
904.02
Bradykinin 2-9
IUPAC Name
(2S)-5-(diaminomethylideneamino)-2-[[(2S)-2-[[(2S)-1-[(2S)-3-hydroxy-2-[[(2S)-3-phenyl-2-[[2-[[(2S)-1-[(2S)-pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]amino]acetyl]amino]propanoyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]-3-phenylpropanoyl]amino]pentanoic acid
Synonyms
Des-Arg1-bradykinin; H-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH; L-prolyl-L-prolyl-glycyl-L-phenylalanyl-L-seryl-L-prolyl-L-phenylalanyl-L-arginine; Bradykinin fragment 2-9; 2-9-Bradykinin
Appearance
White to Off-white Powder
Purity
≥95%
Density
1.46±0.1 g/cm3 (Predicted)
Sequence
PPGFSPFR
Storage
Store at -20°C
Solubility
Soluble in Water
InChI
InChI=1S/C44H61N11O10/c45-44(46)48-20-8-16-30(43(64)65)51-38(59)32(24-28-13-5-2-6-14-28)52-40(61)35-18-10-22-55(35)42(63)33(26-56)53-37(58)31(23-27-11-3-1-4-12-27)50-36(57)25-49-39(60)34-17-9-21-54(34)41(62)29-15-7-19-47-29/h1-6,11-14,29-35,47,56H,7-10,15-26H2,(H,49,60)(H,50,57)(H,51,59)(H,52,61)(H,53,58)(H,64,65)(H4,45,46,48)/t29-,30-,31-,32-,33-,34-,35-/m0/s1
InChI Key
ZZHVXIPXTCBVBE-POFDKVPJSA-N
Canonical SMILES
C1CC(NC1)C(=O)N2CCCC2C(=O)NCC(=O)NC(CC3=CC=CC=C3)C(=O)NC(CO)C(=O)N4CCCC4C(=O)NC(CC5=CC=CC=C5)C(=O)NC(CCCN=C(N)N)C(=O)O
1. Activated central galanin type 1 receptor alleviated insulin resistance in diabetic rat muscle
Le Bu, Xusheng Chang, Qian Yao, Xiaoyun Cheng, Bin Su, Shen Qu, Chunjun Sheng J Neurosci Res . 2016 Oct;94(10):947-55. doi: 10.1002/jnr.23775.
Evidence indicates that central galanin is involved in regulation of insulin resistance in animals. This study investigates whether type 1 galanin receptor (GAL1) in the brain mediates the ameliorative effect of galanin on insulin resistance in skeletal muscles of type 2 diabetic rats. Rats were intracerebroventricularly (i.c.v.) injected with galanin(1-13)-bradykinin(2-9) amide (M617), a GAL1 agonist, and/or Akti-1/2, an Akt inhibitor, via caudal veins once per day for 10 days. Insulin resistance in muscle tissues was evaluated by glucose tolerance and 2-[N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino]-2-deoxyglucose (2-NBDG) tests, peroxisome proliferator-activated receptor-γ (PPARγ), glucose transporter 4 (GLUT4) mRNA expression levels, Akt phosphorylation, and GLUT4 and vesicle-associated membrane protein 2 (VAMP2) concentration at plasma membranes in muscle cells. The results show that i.c.v. treatment with M617 increased glucose tolerance, 2-NBDG uptake, PPARγ levels, Akt phosphorylation, GLUT4 protein, and GLUT4 mRNA expression levels as well as GLUT4 and VAMP2 concentration at plasma membranes. All increases may be blocked by pretreatment with Akti-1/2. These results suggest that activated central GAL1 may trigger the Akt signaling pathway to alleviate insulin resistance in muscle cells. Therefore, the impact of galanin on insulin resistance is mediated mainly by GAL1 in the brain, and the GAL1 agonist may be taken as a potential antidiabetic agent for treatment of type 2 diabetes mellitus. © 2016 Wiley Periodicals, Inc.
2. Regulation of feeding by galnon
Eero Vasar, Honeyleen Manuzon, Ulo Langel, Anders Florén, Urho Abramov, Ariel Brewer, John K Robinson, David J Echevarria, Tamas Bartfai Neuropeptides . 2004 Feb;38(1):55-61. doi: 10.1016/j.npep.2004.01.001.
Galanin is a neuropeptide that has been implicated in multiple bioactivities, inter alia eating disorders. In this study, we have examined the effects of galnon, a novel low molecular weight galanin receptor ligand. Previous studies have shown that galnon acts as a systemically active, blood-brain barrier crossing agonist on galanin signaling both in vitro and in vivo, inhibiting pentylenetetrazole-induced seizures. Here, intracerebroventricular (10-20 microg) and intraperitoneal (1.5-5 mg/kg) administration of galnon induced a strong, dose-dependent reduction of food intake in rats and mice. This reduction in feeding occurred without reducing general activity and was shown to be attenuated by an intracerebroventricular administration of M35, a peptide galanin antagonist. These data demonstrate that galnon is a promising tool for studies of the involvement of galanin in feeding disorders and other behavioral processes.
3. Sensitive mass spectrometric determination of kinin-kallikrein system peptides in light of COVID-19
Bjoern B Burckhardt, Tanja Gangnus Sci Rep . 2021 Feb 4;11(1):3061. doi: 10.1038/s41598-021-82191-7.
The outbreak of COVID-19 has raised interest in the kinin-kallikrein system. Viral blockade of the angiotensin-converting enzyme 2 impedes degradation of the active kinin des-Arg(9)-bradykinin, which thus increasingly activates bradykinin receptors known to promote inflammation, cough, and edema-symptoms that are commonly observed in COVID-19. However, lean and reliable investigation of the postulated alterations is currently hindered by non-specific peptide adsorption, lacking sensitivity, and cross-reactivity of applicable assays. Here, an LC-MS/MS method was established to determine the following kinins in respiratory lavage fluids: kallidin, bradykinin, des-Arg(10)-kallidin, des-Arg(9)-bradykinin, bradykinin 1-7, bradykinin 2-9 and bradykinin 1-5. This method was fully validated according to regulatory bioanalytical guidelines of the European Medicine Agency and the US Food and Drug Administration and has a broad calibration curve range (up to a factor of 103), encompassing low quantification limits of 4.4-22.8 pg/mL (depending on the individual kinin). The application of the developed LC-MS/MS method to nasal lavage fluid allowed for the rapid (~ 2 h), comprehensive and low-volume (100 µL) determination of kinins. Hence, this novel assay may support current efforts to investigate the pathophysiology of COVID-19, but can also be extended to other diseases.
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