Synthesis and biological activity of the first cyclic biphalin analogues |
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Authors: | Mollica Adriano Davis Peg Ma Shou-Wu Porreca Frank Lai Josephine Hruby Victor J |
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Affiliation: | Department of Chemistry, University of Arizona, Tucson, AZ 85721, USA. |
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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. |
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