Studies on analgesic oligopeptides. VI. Further studies of synthesis and biological properties of tripeptide alkylamides, Tyr-D-Arg-Phe-X.

DOI Web Site PubMed 2 Citations

Abstract

Nine analogs based on a structure of Tyr-D-Arg-Phe-X (X=alkylamides or alkylhydrazide containing electoron-withdrawing atoms or groups) were newly synthesized and their biological properties were examined by the opioid receptor binding properties of μ-, δ- and κ-receptors, guinea-pig ileum (GPI) assay and analgesic activity in the tail pinch test after subcutaneous administration in mice. Analogs with X=NHCH2CF3, Sar-ol, or NH(CH2)2CN showed potent activities in the GPI and analgesic assays and high affinity for μ-receptor. An analog with X=taurinamide was found to possess 4-fold higher μ-receptor selectivity than that of [D-Ala2, MePhe4, Gly-ol5]enkephalin (DAGO). The receptor binding properties of previously reported analogs [Chem. Pharm. Bull., 33, 1528 (1985); ibid., 33, 4865 (1985); ibid., 36, 4834 (1988)] were also examined for overall discussion of the structure-activity relationships of this series of tripeptide amides.

Journal

Citations (2)*help

See more

Keywords

Details 詳細情報について

Report a problem

Back to top