o-naphthalenedicarboxaldehyde derivative of 7′-aminonaltrindole as a selective δ-opioid receptor affinity label

Sarika Prabhu Haris, Yan Zhang, Bertrand Le Bourdonnec, Christopher R. McCurdy, Philip S. Portoghese

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

Incorporation of a naphthalene-dialdehyde moiety into the δ antagonist, 6′-aminonaltrindole afforded a potent, selective, irreversible δ-agonist 1. However, flow cytometry studies revealed no time-dependent specific fluorescence, suggesting that both Lys214 and Cys216 at the recognition site are not involved in covalent binding. Molecular simulation studies suggest that compound 1 may form a Schiff base with the ε-amino group of Lys214, which could explain its irreversibility and transformation into a δ-agonist through a conformational change of TM5.

Original languageEnglish (US)
Pages (from-to)3392-3396
Number of pages5
JournalJournal of medicinal chemistry
Volume50
Issue number14
DOIs
StatePublished - Jul 12 2007

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