Helix-inducing α-aminoisobutyric acid in opioid mimetic deltorphin C analogues

…, R Guerrini, S Salvadori, C Bianchi…

Index: Bryant, Sharon D.; Guerrini, Remo; Salvadori, Severo; Bianchi, Clementina; Tomatis, Roberto; Attila, Martti; Lazarus, Lawrence H. Journal of Medicinal Chemistry, 1997 , vol. 40, # 16 p. 2579 - 2587

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Citation Number: 34

Abstract

The achiral symmetric α-aminoisobutyric acid (Aib) replaced the critical N-terminal residues of the amphibian skin opioid deltorphin C (H-Tyr-d-Ala-Phe-Asp-Val-Val-Gly-NH2) without detriment to the physicochemical requirements for δ opioid receptor recognition. Substitutions by the α, α-dialkyl amino acid in place of d-Ala2 or Phe3, or both, exhibited high δ receptor affinity (K iδ= 0.12-3.6 nM) and 5-9-fold greater selectivity (K iμ/K iδ= 5000- ...