On resin click-chemistry-mediated synthesis of novel enkephalin analogues with potent anti-nociceptive activity
Dimmito, Marilisa Pia
Streicher, John M
AffiliationUniv Arizona, Coll Med, Dept Pharmacol
MetadataShow full item record
PublisherNATURE PUBLISHING GROUP
CitationStefanucci, A., Lei, W., Pieretti, S., Novellino, E., Dimmito, M. P., Marzoli, F., ... & Mollica, A. (2019). On resin click-chemistry-mediated synthesis of novel enkephalin analogues with potent anti-nociceptive activity. Scientific reports, 9(1), 5771.
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AbstractHere, 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.
NoteOpen access journal
VersionFinal published version
SponsorsUniversity of Arizona