Synthesis of enkephalin-based affinity labels for delta opioid receptors

DY Maeda, Thomas F. Murray, JE Roth, JV Aldrich

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Affinity labels (irreversible ligands) are useful pharmacological tools to study receptor structure and function. As part of a program to prepare affinity labels based on opioid peptides, we developed a general synthetic strategy to introduce different electrophilic labeling moieties (i.e. isothiocyanate and bromoacetamide) via a p-amino functionality on a phenylalanine residue. The affinity labelling groups were incorporated into the Phe4 position of the delta opioid receptor antagonists ICI-174,864 (1) and N,N-dibenzyl leucine enkephalin (2). Using an orthogonal Boc/Fmoc protection strategy, the common peptide precursors were assembled in solution, the affinity labels introduced and the peptides deprotected. In cloned δ receptors expressed in CHO cells (3), only the isothiocyanate derivative of N,N-dibenzyl leucine enkephalin exhibited wash-resistant inhibition of [3H]DPDPE binding.

Original languageEnglish
Pages (from-to)171-172
Number of pages2
JournalRegulatory Peptides
Volume54
Issue number1
DOIs
StatePublished - Nov 10 1994
Externally publishedYes

Fingerprint

Affinity Labels
delta Opioid Receptor
Enkephalins
Leucine Enkephalin
Labeling
D-Penicillamine (2,5)-Enkephalin
Peptides
Opioid Peptides
Narcotic Antagonists
CHO Cells
Phenylalanine
Pharmacology
Ligands
Derivatives
isothiocyanic acid

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Endocrinology
  • Physiology
  • Neuroscience(all)

Cite this

Synthesis of enkephalin-based affinity labels for delta opioid receptors. / Maeda, DY; Murray, Thomas F.; Roth, JE; Aldrich, JV.

In: Regulatory Peptides, Vol. 54, No. 1, 10.11.1994, p. 171-172.

Research output: Contribution to journalArticle

Maeda, DY ; Murray, Thomas F. ; Roth, JE ; Aldrich, JV. / Synthesis of enkephalin-based affinity labels for delta opioid receptors. In: Regulatory Peptides. 1994 ; Vol. 54, No. 1. pp. 171-172.
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