Abstract
Two partially modified retro-inverso analogues of Leu-enkephalin in which the peptide bond between Gly3-Phe4 was reversed resulted from the incorporation of the Gly3ψ(NH-CO)Phe4 unit. The presence of racemic 2-benzylmalonyl residue led to diastereomeric mixtures of analogues; H-Tyr-D-Ala-gGly-(RS)-mPhe-Leu-NH2 (I) and H-Tyr-Gly-gGly-(RS)-mPhe-Leu-NH2 (II). Analogue I was more potent than analogue II in the binding assay, induced guinea pig ileum assay as well as in antinociceptive tests. Both activities were naloxone reversible. No analgesia was observed after subcutaneous (SC) administration of 100 mg/kg of either I or II. The problems related to configurational lability of the 2-alkylmalonyl residues in partially modified retro-inverso analogues is addressed.
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