136553-81-6

Basic information

• Product Name: BQ-123 SODIUM SALT
• Synonyms: BQ-123;BQ-123 SODIUM SALT;ETA-RECEPTOR ANTAGONIST;C(DTRP-DASP-PRO-DVAL-LEU);CYCLO (D-ALPHA-ASPARTYL-L-PROLYL-D-VALYL-L-LEUCYL-D-TRYPTOPHYL);CYCLO(D-ASP-PRO-D-VAL-LEU-D-TRP);CYCLO(D-ASP-PRO-D-VAL-LEU-DTRP NA);CYCLO(-D-TRP-D-ASP-PRO-D-VAL-LEU)
• CAS NO: 136553-81-6
• Molecular Formula: C₃₁H₄₂N₆O₇
• Molecular Weight: 610.71
• Product Categories: Antagonists;Endothelins;Peptides for Cell Biology;Endothelin receptor
• Mol File: 136553-81-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 978.3°Cat760mmHg
• Flash Point: 545.5°C
• Appearance: /lyophilized powder
• Density: 1.282g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.621
• Storage Temp.: −20°C
• Solubility: Soluble to 0.40 mg/ml in sterile
• PKA: 4.04±0.10(Predicted)
• CAS DataBase Reference: BQ-123 SODIUM SALT(CAS DataBase Reference)
• NIST Chemistry Reference: BQ-123 SODIUM SALT(136553-81-6)
• EPA Substance Registry System: BQ-123 SODIUM SALT(136553-81-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 136553-81-6(Hazardous Substances Data)

Usage

Uses

BQ-123 has been used as a selective endothelin-A receptor antagonist to study its effects on tumor necrosis factor α (TNFα)-induced human airway smooth muscle cells (HASMCs) proliferation. It is also used as endothelin-A receptor antagonist to study its effects on TNFα-induced granulocyte–macrophage colony-stimulating factor (GM-CSF) expression.

Biological Activity

bq-123 is a potent and selective antagonist of eta endothelin receptor with ki values of 1.4 and 1500 nm for eta and etb receptors, respectively.endothelin receptor is a g protein-coupled receptor. eta receptor increases intracellular-free ca2+. also, activation of eta receptor increases vasoconstriction and blood pressure.bq-123 is a selective eta receptor antagonist. in the eta-expressing cells, bq123 (10-6 m) inhibited endothelin-1 (et-1) (10-6 m)-induced [ca2+]i increase by 95% [1]. in rat vascular smooth muscle cells (vsmc), bq-123 inhibited et-1 receptor binding, cellular contraction, [ca2+ ]i mobilization, [3h]thymidine incorporation, map kinase activation and mtt reduction induced by et-1. however, bq-123 didn’t inhibit angiotensin ii (ang ii)- and arginine vasopressin (avp)-induced increases in map kinase activity and [ca2+]i mobilization [2].in spontaneously hypertensive rats (shr), renin hypertensive rats and normotensive rats, bq-123 (16 nm/kg/min) reduced mean arterial pressure in a dose-dependent way in shr. also, bq-123 lowered blood pressure in both renin hypertensive rats and normotensive rats [3]. in a kidney transplantation rat model with reperfusion injury, bq-123 prevented reperfusion injury and inhibited the synthesis and release of et-1,2 [4].

Biochem/physiol Actions

Selective ETA endothelin receptor antagonist.

references

[1]. sakamoto a, yanagisawa m, sawamura t, et al. distinct subdomains of human endothelin receptors determine their selectivity to endothelina-selective antagonist and endothelinb-selective agonists. j biol chem, 1993, 268(12): 8547-8553.[2]. guo x, okada k, fujita n, et al. inhibitory effect of bq-123 on endothelin-1-stimulated mitogen-activated protein kinase and cell growth of rat vascular smooth muscle cells. hypertens res, 1996, 19(1): 23-30.[3]. douglas sa, gellai m, ezekiel m, et al. bq-123, a selective endothelin subtype a-receptor antagonist, lowers blood pressure in different rat models of hypertension. j hypertens, 1994, 12(5): 561-567.[4]. büyükgebiz o, aktan ao, haklar g, et al. bq-123, a specific endothelin (eta) receptor antagonist, prevents ischemia-reperfusion injury in kidney transplantation. transpl int, 1996, 9(3): 201-207.

InChI:InChI=1/C31H42N6O7/c1-16(2)12-21-27(40)33-22(13-18-15-32-20-9-6-5-8-19(18)20)28(41)35-23(14-25(38)39)31(44)37-11-7-10-24(37)29(42)36-26(17(3)4)30(43)34-21/h5-6,8-9,15-17,21-24,26,32H,7,10-14H2,1-4H3,(H,33,40)(H,34,43)(H,35,41)(H,36,42)(H,38,39)

Upstream product

• 166760-86-7 H-D-Trp-D-Asp(O-t-Bu)-Pro-D-Val-Leu-NHNH₂ 
• 13139-15-6 N-tert-butoxycarbonyl-L-leucine 
• 22838-58-0 Boc-D-Val-OH 
• 5241-64-5 Boc-D-Trp-OH 
• 214630-04-3 (R)-2-tert-Butoxycarbonylamino-succinic acid 1-(9H-fluoren-9-ylmethyl) ester 
• 160195-16-4 cyclo-(D-Trp-D-Asp(O-t-Bu)-Pro-D-Val-Leu-) 

Relevant articles and documents

Rediscovering an endothelin antagonist (BQ-123): A self-deconvoluting cyclic pentapeptide library

A 'self-deconvoluting' cyclic pentapeptide library, designed to produce 82 944 head-to-tail-linked peptides in 48 vials, has been prepared. The mixture included amine acids found in a recently optimized endothelin antagonist, BQ-123, originally isolated from microbial sources by Banyu investigators. Using a positional scan approach, the most potent of 12 residues at each of the four variable positions uniquely rediscovered the BQ- 123 sequence or cyclo(L-Pro-D-Val-L-Leu-D-Trp-D-Asp). Resynthesis of the four most potent amine acid combinations gave the following values of relative potency: cyclo(L-Pro-D-Val-L-Leu-D-Trp-D-Asp) or BQ-123 = 1.0, cyclo(L-Pro- D-Pro-L-Leu-D-Trp-D-Asp) = 0.0, cyclo(L-Pro-D-Pro-L-Trp-D-Trp-D-Asp) = 0.0, and cyclo(L-Pro-D-Val-L-Trp-D-Trp-D-Asp) = 0.1. This study reflects the first time that the positional scan approach has been applied to cyclic peptide libraries using a known target. Although no analogs more potent than BQ-123 were discovered, our results provide verification of our synthetic methods for preparing head-to-tail cyclic peptide libraries and also lend support to the use of carefully designed sublibraries for the rapid elucidation of potential leads within a relatively constrained set of peptide macrocycles.

Cyclic Pentapeptide Endothelin Antagonists with High ETA Selectivity. Potency- and Solubility-Enhancing Modifications

-