Synthesis and biological activity of the first cyclic biphalin analogues

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

Research output: Contribution to journalArticle

37 Scopus citations

Abstract

Biphalin is a linear octapeptide with strong opioid activity. Its structure is based on two identical sequences derived from enkephalins joined C-terminal to C-terminal by an hydrazide bridge (Tyr-D-Ala-Gly-Phe-NH-NH ← Phe ← Gly ← D-Ala ← Tyr). In this study we present the design, synthesis, and biological evaluation of the first cyclic biphalin analogues. d-Alanine residues in positions 2, 2′ of the parent peptide were replaced by d- and l-cysteine and an intramolecular disulfide bond between the cysteine thiol groups was introduced. We obtained two cyclic analogues with quite different biological profiles.

Original languageEnglish (US)
Pages (from-to)367-372
Number of pages6
JournalBioorganic and Medicinal Chemistry Letters
Volume16
Issue number2
DOIs
StatePublished - Jan 15 2006

Keywords

  • Biphalin
  • Cyclic peptides

ASJC Scopus subject areas

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

Fingerprint Dive into the research topics of 'Synthesis and biological activity of the first cyclic biphalin analogues'. Together they form a unique fingerprint.

  • Cite this