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(D-Arg0,Hyp3,Igl5,D-Igl7,Oic8)-Bradykinin

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

(D-Arg0,Hyp3,Igl5,D-Igl7,Oic8)-Bradykinin, a bradykinin antagonist, shows high affinity for both BK receptors.

Category

Peptide Inhibitors

Catalog number

BAT-015372

CAS number

180981-09-3

Molecular Formula

C64H95N19O13

Molecular Weight

1338.56

(D-Arg0,Hyp3,Igl5,D-Igl7,Oic8)-Bradykinin

Specification
Reference Reading

IUPAC Name

(2S)-2-[[(2S,3aS,7aS)-1-[(2R)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S,4R)-1-[(2S)-1-[(2S)-2-[[(2R)-2-amino-5-(diaminomethylideneamino)pentanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]-4-hydroxypyrrolidine-2-carbonyl]amino]acetyl]amino]-2-(2,3-dihydro-1H-inden-2-yl)acetyl]amino]-3-hydroxypropanoyl]amino]-2-(2,3-dihydro-1H-inden-2-yl)acetyl]-2,3,3a,4,5,6,7,7a-octahydroindole-2-carbonyl]amino]-5-(diaminomethylideneamino)pentanoic acid

Synonyms

B9430; H-D-Arg-Arg-Pro-Hyp-Gly-Gly(indan-2-yl)-Ser-D-Gly(indan-2-yl)-Oic-Arg-OH; (N-(D-arginyl-L-arginyl-L-prolyl-(4R)-4-hydroxy-L-prolyl-glycyl-2-indan-2-yl-L-glycyl-L-seryl-2-indan-2-yl-D-glycyl)-(2S,3aS,7aS)-octahydroindole-2-carbonyl)-L-arginine; H-D-Arg-Arg-Pro-Hyp-Gly-Igl-Ser-D-Igl-Oic-Arg-OH; L-Arginine, D-arginyl-L-arginyl-L-prolyl-(4R)-4-hydroxy-L-prolylglycyl-(2S)-2-(2,3-dihydro-1H-inden-2-yl)glycyl-L-seryl-(2R)-2-(2,3-dihydro-1H-inden-2-yl)glycyl-(2S,3aS,7aS)-octahydro-1H-indole-2-carbonyl-

Appearance

White to Off-white Solid

Purity

≥95%

Density

1.6±0.1 g/cm3

Sequence

RRP-Hyp-G-Igl-S-DIgl-Oic-R

Storage

Store at -20°C

Solubility

Soluble in Water

Application

Bradykinin Receptor Antagonists

InChI

InChI=1S/C64H95N19O13/c65-42(16-7-21-72-62(66)67)53(87)76-43(17-8-22-73-63(68)69)58(92)81-24-10-20-47(81)59(93)82-32-41(85)30-48(82)55(89)75-31-50(86)79-51(39-25-34-11-1-2-12-35(34)26-39)57(91)78-45(33-84)54(88)80-52(40-27-36-13-3-4-14-37(36)28-40)60(94)83-46-19-6-5-15-38(46)29-49(83)56(90)77-44(61(95)96)18-9-23-74-64(70)71/h1-4,11-14,38-49,51-52,84-85H,5-10,15-33,65H2,(H,75,89)(H,76,87)(H,77,90)(H,78,91)(H,79,86)(H,80,88)(H,95,96)(H4,66,67,72)(H4,68,69,73)(H4,70,71,74)/t38-,41+,42+,43-,44-,45-,46-,47-,48-,49-,51-,52+/m0/s1

InChI Key

PVNQRMOWAXFQHU-REOWKGFMSA-N

Canonical SMILES

C1CCC2C(C1)CC(N2C(=O)C(C3CC4=CC=CC=C4C3)NC(=O)C(CO)NC(=O)C(C5CC6=CC=CC=C6C5)NC(=O)CNC(=O)C7CC(CN7C(=O)C8CCCN8C(=O)C(CCCN=C(N)N)NC(=O)C(CCCN=C(N)N)N)O)C(=O)NC(CCCN=C(N)N)C(=O)O

1. Partial agonists and full antagonists at the human and murine bradykinin B1 receptors

T MacNeil, J F Hess, D L Hreniuk, L H Van der Ploeg, S Feighner Can J Physiol Pharmacol . 1997 Jun;75(6):735-40.

We developed a functional assay to evaluate the activity of kinin peptides at the human and mouse bradykinin (BK) B1 receptors. The photoprotein aequorin expressed in 293-AEQ17 cells was used to measure calcium mobilization due to activation of the human or mouse B1 receptors by kinin peptides. The B1 agonists des-Arg9-BK and des-Arg10-kallidin activated the human receptor (EC50 = 112 and 5 nM, respectively), whereas the B1 peptide antagonists des-Arg9,Leu8-BK and des-Arg10,Leu9-kallidin showed no activation. At the murine receptor, the agonists des-Arg9-BK and des-Arg10-kallidin activated the receptor with EC50 values of 39 and 23 nM, respectively. In contrast, the two peptide antagonists showed significant agonism at the murine receptor. Thirty-nine and 44% agonism of the mouse receptor was observed with des-Arg9,Leu8-BK (EC50 = 56 nM) and des-Arg10,Leu9-kallidin (EC50 = 177 nM). Two recently described kinin analogues, [Lys-Lys0,Hyp3,Igl5,D-Igl7,Oic8,des-Arg9]B K and [D-Arg0,Hyp3,Igl5,D-Igl7, Oic8,des-Arg9]BK (B9858 and des-Arg9-B9430), failed to agonize the mouse receptor. These peptides were potent antagonists of des-Arg10-kallidin- and des-Arg9-BK-induced bioluminescence at the cloned human and mouse B1 receptors.