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[Phe8Ψ(CH-NH)-Arg9]-Bradykinin

Selective B2 agonist CAS# 118122-39-7

[Phe8Ψ(CH-NH)-Arg9]-Bradykinin

Catalog No. BCC5995----Order now to get a substantial discount!

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[Phe8Ψ(CH-NH)-Arg9]-Bradykinin: 5mg $1265 In Stock
[Phe8Ψ(CH-NH)-Arg9]-Bradykinin: 10mg Please Inquire In Stock
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[Phe8Ψ(CH-NH)-Arg9]-Bradykinin: 500mg Please Inquire Please Inquire
[Phe8Ψ(CH-NH)-Arg9]-Bradykinin: 1000mg Please Inquire Please Inquire
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Chemical structure

[Phe8Ψ(CH-NH)-Arg9]-Bradykinin

3D structure

Chemical Properties of [Phe8Ψ(CH-NH)-Arg9]-Bradykinin

Cas No. 118122-39-7 SDF Download SDF
PubChem ID 3082903 Appearance Powder
Formula C50H75N15O10 M.Wt 1046.23
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble to 1 mg/ml in water
Sequence RPPGFSPFR

(Modifications: Phe-8 - Arg-9 peptide bond replaced with Ψ-(CH2-NH))

Chemical Name (2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[2-[[(2S)-1-[(2S)-1-[(2S)-2-amino-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-3-hydroxypropanoyl]pyrrolidine-2-carbonyl]amino]-3-phenylpropyl]amino]-5-(diaminomethylideneamino)pentanoic acid
SMILES C1CC(N(C1)C(=O)C2CCCN2C(=O)C(CCCN=C(N)N)N)C(=O)NCC(=O)NC(CC3=CC=CC=C3)C(=O)NC(CO)C(=O)N4CCCC4C(=O)NC(CC5=CC=CC=C5)CNC(CCCN=C(N)N)C(=O)O
Standard InChIKey XKJBISGEHGXKBF-TZPCGENMSA-N
Standard InChI InChI=1S/C50H75N15O10/c51-34(16-7-21-56-49(52)53)45(71)65-25-11-20-40(65)47(73)64-24-9-18-38(64)43(69)59-29-41(67)61-36(27-32-14-5-2-6-15-32)42(68)62-37(30-66)46(72)63-23-10-19-39(63)44(70)60-33(26-31-12-3-1-4-13-31)28-58-35(48(74)75)17-8-22-57-50(54)55/h1-6,12-15,33-40,58,66H,7-11,16-30,51H2,(H,59,69)(H,60,70)(H,61,67)(H,62,68)(H,74,75)(H4,52,53,56)(H4,54,55,57)/t33-,34-,35-,36-,37-,38-,39-,40-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of [Phe8Ψ(CH-NH)-Arg9]-Bradykinin

DescriptionSelective bradykinin B2 receptor agonist that is resistant to carboxypeptidase cleavage. 5-fold more potent and exhibits a more prolonged duration of action than bradykinin (Cat No. 3004) in vivo.

[Phe8Ψ(CH-NH)-Arg9]-Bradykinin Dilution Calculator

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References on [Phe8Ψ(CH-NH)-Arg9]-Bradykinin

International union of pharmacology. XLV. Classification of the kinin receptor family: from molecular mechanisms to pathophysiological consequences.[Pubmed:15734727]

Pharmacol Rev. 2005 Mar;57(1):27-77.

Kinins are proinflammatory peptides that mediate numerous vascular and pain responses to tissue injury. Two pharmacologically distinct kinin receptor subtypes have been identified and characterized for these peptides, which are named B1 and B2 and belong to the rhodopsin family of G protein-coupled receptors. The B2 receptor mediates the action of bradykinin (BK) and lysyl-bradykinin (Lys-BK), the first set of bioactive kinins formed in response to injury from kininogen precursors through the actions of plasma and tissue kallikreins, whereas the B(1) receptor mediates the action of des-Arg9-BK and Lys-des-Arg9-BK, the second set of bioactive kinins formed through the actions of carboxypeptidases on BK and Lys-BK, respectively. The B2 receptor is ubiquitous and constitutively expressed, whereas the B1 receptor is expressed at a very low level in healthy tissues but induced following injury by various proinflammatory cytokines such as interleukin-1beta. Both receptors act through G alpha(q) to stimulate phospholipase C beta followed by phosphoinositide hydrolysis and intracellular free Ca2+ mobilization and through G alpha(i) to inhibit adenylate cyclase and stimulate the mitogen-activated protein kinase pathways. The use of mice lacking each receptor gene and various specific peptidic and nonpeptidic antagonists have implicated both B1 and B2 receptors as potential therapeutic targets in several pathophysiological events related to inflammation such as pain, sepsis, allergic asthma, rhinitis, and edema, as well as diabetes and cancer. This review is a comprehensive presentation of our current understanding of these receptors in terms of molecular and cell biology, physiology, pharmacology, and involvement in human disease and drug development.

Kinin receptors: functional aspects.[Pubmed:12489786]

Int Immunopharmacol. 2002 Dec;2(13-14):1729-39.

Two types of receptors (B1R, B2R) for kinins are defined in mammalian species. Comparative experiments involving recombinant fusion proteins consisting of rabbit B1R or B2R fused to GFP-related proteins are exploited to study the regulation of the response to kinins at the receptor level. The following points will be briefly reviewed and supported by some novel data. (1) The constitutive B2Rs are internalized upon agonist stimulation, but completely recycled to the cell surface; however, B2R destruction can be achieved following limited proteolysis (extracellular trypsin, neutrophil proteases), a plausible down-regulation mechanism in pathology. (2) The inducible B1Rs, stimulated by des-Arg9-kinins, are not phosphorylated nor internalized upon agonist stimulation, but rather undergo a reversible redistribution to caveolae-related rafts. B2Rs are also subjected to this translocation, but only transiently (before endocytosis). (3) Based on the analysis of rabbit aortic smooth muscle cells, B1R induction by cytokines is dependent on nuclear factor KB in rabbit vascular tissue, but exogenous kinins acting on either receptor type do not induce B1R expression.

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