Cyclic hexapeptide endothelin receptor antagonists highly potent for both receptor subtypes ETA and ETB

Biochem Biophys Res Commun. 1994 May 16;200(3):1708-12. doi: 10.1006/bbrc.1994.1649.

Abstract

A cyclic hexapeptide, cyclo(-D-Asp-Trp-Asp-D-Leu-Leu-D-Trp-), designed from cyclo(-D-Glu-Ala-D-alloisoleucyl-Leu-D-Trp-), an ETA receptor-selective antagonist, possessed not only affinity similar to that of BQ-123 for ETA but also higher affinity for ETB than BQ-123. Further modification led to the discovery of cyclo(-D-Asp-Asp(Php)-Asp-D-Thg-Leu-D-Trp-) (Asp(Php): 1-beta-aspartyl-4-phenylpiperazine; Thg: 2-(2-thienyl)glycine) that inhibited [125I]ET-1 binding to the ETA and ETB receptors with IC50 values of 0.082 nM and 120 nM, respectively. Although this compound possesses 1470-fold less affinity for ETB than for ETA, it behaves as a non-selective antagonist that equipotently inhibits vasoconstriction mediated by both receptor subtypes ETA and ETB.

MeSH terms

  • Amino Acid Sequence
  • Animals
  • Cattle
  • Cell Membrane / drug effects
  • In Vitro Techniques
  • Molecular Sequence Data
  • Muscle Relaxation / drug effects
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / pharmacology*
  • Receptors, Endothelin / drug effects*
  • Swine

Substances

  • Peptides, Cyclic
  • Receptors, Endothelin