109333-26-8

Basic information

• Product Name: (D-ARG0,HYP3,D-PHE7)-BRADYKININ
• Synonyms: npc567;H-D-ARG-ARG-PRO-HYP-GLY-PHE-SER-D-PHE-PHE-ARG-OH;D-ARG-ARG-PRO-HYP-GLY-PHE-SER-D-PHE-PHE-ARG;D-ARG-ARG-PRO-HYDROXY-PRO-GLY-PHE-SER-D-PHE-PHE-ARG;D-ARG-[HYP3,D-PHE7]-BRADYKININ;(D-ARG0,HYP3,D-PHE7)-BRADYKININ;(D-Arg0,Hyp3,D-Phe7)bradikinin;D-Arg-L-Arg-L-Pro-4-Hydroxy-L-Pro-Gly-L-Phe-L-Ser-D-Phe-L-Phe-L-Arg-OH
• CAS NO: 109333-26-8
• Molecular Formula: C60H87N19O13
• Molecular Weight: 1282.45
• Mol File: 109333-26-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.48g/cm³
• Refractive Index: 1.69
• Storage Temp.: −20°C
• CAS DataBase Reference: (D-ARG0,HYP3,D-PHE7)-BRADYKININ(CAS DataBase Reference)
• NIST Chemistry Reference: (D-ARG0,HYP3,D-PHE7)-BRADYKININ(109333-26-8)
• EPA Substance Registry System: (D-ARG0,HYP3,D-PHE7)-BRADYKININ(109333-26-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 109333-26-8(Hazardous Substances Data)

Usage

Description

(D-ARG0,HYP3,D-PHE7)-BRADYKININ is a ten-membered oligopeptide consisting of D-arginyl, L-arginyl, L-prolyl, (4R)-4-hydroxy-L-prolyl, glycyl, L-phenylalanyl, L-seryl, -phenylalanyl, L-phenylalanyl, and L-arginine residues joined in sequence. It is a modified form of the peptide hormone Bradykinin, which plays a crucial role in the regulation of vascular permeability and blood pressure.

Uses

Used in Pharmaceutical Industry:
(D-ARG0,HYP3,D-PHE7)-BRADYKININ is used as a therapeutic agent for treating various cardiovascular and inflammatory conditions. Its ability to modulate vascular permeability and blood pressure makes it a potential candidate for the development of drugs targeting hypertension, angina, and other related disorders.
Used in Research Applications:
(D-ARG0,HYP3,D-PHE7)-BRADYKININ is used as a research tool for studying the molecular mechanisms underlying the regulation of vascular permeability and blood pressure. It helps researchers to understand the role of kinin receptors and their signaling pathways in physiological and pathological processes.
Used in Drug Development:
(D-ARG0,HYP3,D-PHE7)-BRADYKININ is used as a lead compound in the development of new drugs targeting kinin receptors. Its unique structure and biological activity provide insights into the design of novel therapeutic agents with improved efficacy and selectivity for treating cardiovascular and inflammatory diseases.

InChI:InChI=1/C60H87N19O13/c61-39(20-10-24-68-58(62)63)49(83)73-40(21-11-25-69-59(64)65)55(89)78-27-13-23-46(78)56(90)79-33-38(81)31-47(79)54(88)71-32-48(82)72-42(28-35-14-4-1-5-15-35)50(84)77-45(34-80)53(87)76-44(30-37-18-8-3-9-19-37)52(86)75-43(29-36-16-6-2-7-17-36)51(85)74-41(57(91)92)22-12-26-70-60(66)67/h1-9,14-19,38-47,80-81H,10-13,20-34,61H2,(H,71,88)(H,72,82)(H,73,83)(H,74,85)(H,75,86)(H,76,87)(H,77,84)(H,91,92)(H4,62,63,68)(H4,64,65,69)(H4,66,67,70)/t38-,39-,40+,41+,42+,43+,44-,45+,46+,47+/m1/s1

Upstream product

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Relevant articles and documents

A New Class of Bradykinin Antagonists: Synthesis and in Vitro Activity of Bissuccinimidoalkane Peptide Dimers

A systematic study on the dimerization of the bradykinin (BK) antagonist D-Arg0-Arg1-Pro2-Hyp3-Gly4-Phe5-Ser6-D-Phe7-Leu8-Arg9 has been performed.The first part of this study involved compounds wherein dimerization was carried out by sequentially replacing each amino acid with cysteine and cross-linking with bismaleimidohexane.The second part of this study utilized a series of bissuccinimidoalkane dimers wherein the intervening methylene chain was varied systematically from n = 2 to n = 12 while the point of dimerization was held constant at position 6.The biological activities of these dimers were then evaluated on BK-induced smooth muscle contraction in two different isolated tissue preparations: guinea pig ileum (GPI) and rat uterus (RU).Several of the dimeric BK antagonists displayed remarkable activites and long durations of action.In addition, dimerization at position 4, 7, 8, or 9 produced dimeric analogues with markedly reduced potency.Rank order of antagonist potency as a function of dimerization position is as follows: rat uterus, 6 > 5 > 0 > 2 > 1 >3 >> 4, 7, 8, 9; guinea pig ileum, 6 > 5 > 3 > 2 > 1 > 0 >> 4, 7, 8, 9.Evaluation of the linker length as represented by the number of methylene units indicated an optimal distance between the two monomeric peptides of six to eight methylene moieties.These studies also revealed that the carbon-chain length significantly affected the duration of action in vitro and resulted in partial agonism effects when n > 8.The optimum activity in vitro was achieved with dimerization at position 6 and n = 6 (designated herein as compound 25; alternatively, CP-0127).Similar effects in potency were also seen when the monomeric antagonist D-Arg0-Arg1-Pro2-Hyp3-Gly4-Phe5-Ser6-D-Phe7-Phe8-Arg9 (NPC-567) was dimerized using similar chemistry.These results suggest that the development of BK antagonists of significant therapeutic potential may be possible using a dimerization strategy that can overcome the heretofore limiting problems of potency and in vivo duration of action found with many of the BK antagonists in the literature.