Solid phase synthesis and evaluation of Tyr-Tic-Phe-Phe(p-NHCOCH(2)Br) ([Phe(p-bromoacetamide)(4)]TIPP), a potent affinity label for delta opioid receptors

J Med Chem. 2002 Aug 29;45(18):3820-3. doi: 10.1021/jm020290p.

Abstract

Derivatives of the delta opioid receptor selective peptide Tyr-Tic-Phe-Phe-OH (TIPP) containing a p-bromoacetamide moiety on the phenyl ring of Phe(3) or Phe(4) were prepared by solid phase synthesis. [Phe(p-NHCOCH(2)Br)(4)]TIPP exhibited high affinity for cloned delta receptors (IC(50) = 5.4 nM), and incubation with only 2.5 nM resulted in 85% wash resistant inhibition of radioligand binding to delta receptors. Therefore, this peptide is a potent affinity label for further study of delta opioid receptors.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Affinity Labels / chemical synthesis*
  • Affinity Labels / chemistry
  • Affinity Labels / pharmacology
  • Animals
  • Guinea Pigs
  • Ileum / drug effects
  • Ileum / physiology
  • In Vitro Techniques
  • Ligands
  • Male
  • Mice
  • Oligopeptides / chemical synthesis*
  • Oligopeptides / chemistry
  • Oligopeptides / pharmacology
  • Radioligand Assay
  • Receptors, Opioid, delta / agonists
  • Receptors, Opioid, delta / antagonists & inhibitors
  • Receptors, Opioid, delta / drug effects*
  • Tetrahydroisoquinolines*
  • Vas Deferens / drug effects
  • Vas Deferens / physiology

Substances

  • Affinity Labels
  • Ligands
  • Oligopeptides
  • Receptors, Opioid, delta
  • Tetrahydroisoquinolines
  • tyrosyl-1,2,3,4-tetrahydroisoquinoline-3-carbonyl-phenylalanyl-4-bromoacetamidophenylalanine