X-ray Crystal Structure of the Opioid Ligand Naltrexonazine

Z. Urbanczyk-Lipkowska, A. W. Lipkowski, M. C. Etter, E. F. Hahn, G. W. Pasternak, P. S. Portoghese

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

The anti-anti isomer of naltrexonazine (1) was synthesized, and its configuration was confirmed by X-ray crystallography. The syn-anti isomer is readily converted to 1 under acidic conditions. The apparent equal receptor binding of 1 and syn-anti isomer indicates that isomerization of the azine moiety may take place under the conditions of biological evaluation. Two possible explanations for wash-resistant binding of 1 to opioid receptors are presented. The first possibility involves a noncovalent interaction of the ligand with the opioid receptor, and the second considers covalent binding by a receptor-based sulfhydryl group.

Original languageEnglish (US)
Pages (from-to)1489-1494
Number of pages6
JournalJournal of medicinal chemistry
Volume30
Issue number8
DOIs
StatePublished - Aug 1 1987

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