On resin click-chemistry-mediated synthesis of novel enkephalin analogues with potent anti-nociceptive activity

Azzurra Stefanucci, Wei Lei, Stefano Pieretti, Ettore Novellino, Marilisa Pia Dimmito, Francesca Marzoli, John M Streicher, Adriano Mollica

Research output: Contribution to journalArticlepeer-review

Abstract

Here, we report the chemical synthesis of two DPDPE analogues 7a (NOVA1) and 7b (NOVA2). This entailed the solid-phase synthesis of two enkephalin precursor chains followed by a CuI-catalyzed azide-alkyne cycloaddition, with the aim of improving in vivo analgesic efficacy versus DPDPE. NOVA2 showed good affinity and selectivity for the μ-opioid receptor (KI of 59.2 nM, EC50 of 12.9 nM, EMax of 87.3%), and long lasting anti-nociceptive effects in mice when compared to DPDPE.

Original languageEnglish
Pages (from-to)5771
JournalSci. Rep.
Volume9
Issue number1
DOIs
Publication statusPublished - Apr 8 2019

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