Synthesis and biological evaluation of new biphalin analogues with non-hydrazine linkers

Adriano Mollica, Peg Davis, Shou Wu Ma, Josephine Lai, Frank Porreca, Victor J. Hruby

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

Abstract

Biphalin is a potent opioid peptide agonist, with a palandromic structure, composed of two enkephalin-like active fragments connected tail to tail by a hydrazine linker (Tyr-D-Ala-Gly-Phe-NH-NH<-Phe<-Gly<-D-Ala<-Tyr). This study presents the synthesis and in vitro bioassays of six new biphalin analogues with three different non-hydrazine linkers, some of which have higher binding affinity and bioactivity than biphalin.

Original languageEnglish (US)
Pages (from-to)2471-2475
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume15
Issue number10
DOIs
StatePublished - May 16 2005

Keywords

  • Biphalin analogues
  • Linkers
  • Opioid agonists
  • Structure-activity relationship

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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