158873-14-4

Basic information

• Product Name: (N-ME-D-PHE7)-BRADYKININ
• Synonyms: (N-ME-D-PHE7)-BRADYKININ;H-ARG-PRO-PRO-GLY-PHE-SER-N-ME-D-PHE-PHE-ARG-OH
• CAS NO: 158873-14-4
• Molecular Formula: C55H77N15O11
• Molecular Weight: 1124.29
• Mol File: 158873-14-4.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Density: 1.42±0.1 g/cm3(Predicted)
• Storage Temp.: -15°C
• PKA: 3.33±0.10(Predicted)
• CAS DataBase Reference: (N-ME-D-PHE7)-BRADYKININ(CAS DataBase Reference)
• NIST Chemistry Reference: (N-ME-D-PHE7)-BRADYKININ(158873-14-4)
• EPA Substance Registry System: (N-ME-D-PHE7)-BRADYKININ(158873-14-4)

Safety Data

• Hazardous Substances Data: 158873-14-4(Hazardous Substances Data)

Usage

General Description

(N-Me-D-Phe7)-bradykinin is a synthetic peptide that is derived from bradykinin, a vasoactive nonapeptide. This chemical is a potent agonist for the B1 receptor and is used in research to study the physiological effects of bradykinin and its related peptides. It has been shown to induce vasodilation, hypotension, and smooth muscle contraction, and is also involved in pain sensation and inflammation. Additionally, (N-Me-D-Phe7)-bradykinin has been investigated for its potential therapeutic applications in conditions such as diabetes, hypertension, and asthma.

Upstream product

• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 37553-65-4 Boc-N-Me-Phe-OH 
• 59524-02-6 N-tert-butoxycarbonyl-L-serine benzyl ester 
• 37553-65-4 N-tert-butoxycarbonyl-N-methyl-D-phenylalanine 

Relevant articles and documents

Highly selective bradykinin agonists and antagonists with replacement of proline residues by N-methyl-D- and L-phenylalanine

For further studies on the structural and conformational requirements of positions 2, 3, and 7 in the bradykinin sequence, we replaced the proline residues by the more hydrophobic and conformationally restricted N-methyl-L- and D-phenylalanine (NMF). The biological activities of the new analogs were evaluated on rat uterus, guinea pig ileum, and guinea pig lung strip. Receptor binding of the analogs was studied in membranes from rat uterus and guinea pig ileum. Influence of bradykinin analogs on the release of cytokines from mouse spleen cell cultures was also measured. Bradykinin analogs were synthesized by the solid phase method, using Boc strategy on PAM or Merrifield resins. The best results in the formation of the N-methylamide bond were obtained with the coupling reagent PyBrop. In position 7 the substitution of D-Phe by D-NMF, retaining the configuration of the amino acid, converts bradykinin antagonists into agonists. The bradykinin analogs with D-NMF at position 7 gave the highest known tissue selectivity for rat uterus among agonists. [L-NMF2]bradykinin has moderate agonist activity on rat uterus but antagonist activity on guinea pig lung strip. It represents a new antagonist for B2 receptors without any replacement at position 7. The same analog completely inhibits bradykinin-evoked cytokine expression by mononuclear cells.