Solid phase synthesis and evaluation of Tyr-Tic-Phe-Phe(p-NHCOCH2Br) ([Phe(p-bromoacetamide)4]TIPP), a potent affinity label for δ opioid receptors

Vivek Kumar, Thomas F. Murray, Jane V. Aldrich

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Derivatives of the δ opioid receptor selective peptide Tyr-Tic-Phe-Phe-OH (TIPP) containing a p-bromoacetamide moiety on the phenyl ring of Phe3 or Phe4 were prepared by solid phase synthesis. [Phe(p-NHCOCH2Br)4]TIPP exhibited high affinity for cloned δ receptors (IC50 = 5.4 nM), and incubation with only 2.5 nM resulted in 85% wash resistant inhibition of radioligand binding to δ receptors. Therefore, this peptide is a potent affinity label for further study of δ opioid receptors.

Original languageEnglish
Pages (from-to)3820-3823
Number of pages4
JournalJournal of Medicinal Chemistry
Volume45
Issue number18
DOIs
StatePublished - Aug 29 2002
Externally publishedYes

Fingerprint

phenylalanylphenylalanine
Affinity Labels
Tics
Solid-Phase Synthesis Techniques
Opioid Receptors
Peptides
Inhibitory Concentration 50
Derivatives
tyrosyl-1,2,3,4-tetrahydroisoquinoline-3-carbonyl-phenylalanyl-4-bromoacetamidophenylalanine

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Solid phase synthesis and evaluation of Tyr-Tic-Phe-Phe(p-NHCOCH2Br) ([Phe(p-bromoacetamide)4]TIPP), a potent affinity label for δ opioid receptors. / Kumar, Vivek; Murray, Thomas F.; Aldrich, Jane V.

In: Journal of Medicinal Chemistry, Vol. 45, No. 18, 29.08.2002, p. 3820-3823.

Research output: Contribution to journalArticle

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abstract = "Derivatives of the δ opioid receptor selective peptide Tyr-Tic-Phe-Phe-OH (TIPP) containing a p-bromoacetamide moiety on the phenyl ring of Phe3 or Phe4 were prepared by solid phase synthesis. [Phe(p-NHCOCH2Br)4]TIPP exhibited high affinity for cloned δ receptors (IC50 = 5.4 nM), and incubation with only 2.5 nM resulted in 85{\%} wash resistant inhibition of radioligand binding to δ receptors. Therefore, this peptide is a potent affinity label for further study of δ opioid receptors.",
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