7-Spiroindanyl derivatives of naltrexone and oxymorphone as selective ligands for δ opioid receptors

S. Ohkawa, B. DiGiacomo, D. L. Larson, A. E. Takemori, P. S. Portoghese

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

A series consisting of spiroindanyl (5-7), benzospiroindanyl (8-10), and spiroperinaphthyl (11) derivatives of naltrexone and oxymorphone were synthesized in order to investigate the role of an orthogonal-oriented 'address' for δ opioid receptors. All of the ligands exhibited a preference for δ receptors in vitro. The 7-benzospiroindanyl derivative 8 (BSINTX) was the most selective δ opioid receptor antagonist in vitro. In mice BSINTX antagonized the δ1-selective agonist, [D-Pen2,D-Pen5]enkephalin without significantly affecting the antinociceptive potency of δ2, μ, and κ agonists. The results of this study are consistent with an orthogonally- oriented address favoring δ1 activity.

Original languageEnglish (US)
Pages (from-to)1720-1725
Number of pages6
JournalJournal of medicinal chemistry
Volume40
Issue number11
DOIs
StatePublished - May 23 1997

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