A novel N-terminal cyclic dynorphin A analogue cycloN,5[Trp3,Trp4,Glu5] dynorphin A-(1-11)NH2 that lacks the basic N-terminus

Balvinder S. Vig, Thomas F. Murray, Jane V. Aldrich

Research output: Contribution to journalArticle

31 Scopus citations

Abstract

A novel N-terminal-to-side chain cyclic dynorphin A analogue lacking the basic N-terminus was designed based on Ac[Lys2,Trp3,Trp4,D-Ala8] dynorphin A-(1-11)NH2 (Wan et al. J. Med. Chem. 1999, 42, 3011-3013). cycloN,5- [Trp3,Trp4, Glu5]dynorphin A-(1-11)NH2 showed similar κ opioid receptor affinity (Ki = 27 nM) and selectivity (Ki ratio (κ/μ/δ) = 1/12/330) to the linear peptide and antagonized dynorphin A-(1-13)NH2 at κ opioid receptors. This is the first opioid peptide cyclized through the N-terminus that retains high opioid receptor affinity.

Original languageEnglish (US)
Pages (from-to)1279-1282
Number of pages4
JournalJournal of Medicinal Chemistry
Volume46
Issue number8
DOIs
StatePublished - Apr 10 2003
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Molecular Medicine
  • Drug Discovery

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