Opiate receptor binding properties of morphine-, dihydromorphine-, and codeine 6-O-sulfate ester congeners

Peter A. Crooks, Santosh G. Kottayil, Abeer M. Al-Ghananeem, Stephen R. Byrn, D. Allan Butterfield

Research output: Contribution to journalArticlepeer-review

27 Scopus citations

Abstract

A series of 3-O-acyl-6-O-sulfate esters of morphine, dihydromorphine, N-methylmorphinium iodide, codeine, and dihydrocodeine were prepared and evaluated for their ability to bind to μ-, δ-, κ1-, κ2-, and κ3-opiate receptors. Several compounds exhibited good affinity for the μ-opiate receptor. Morphine-3-O-propionyl-6-O-sulfate had four times greater affinity than morphine at the μ-opiate receptor and was the most selective compound at this receptor subtype.

Original languageEnglish
Pages (from-to)4291-4295
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume16
Issue number16
DOIs
StatePublished - Aug 15 2006

Bibliographical note

Funding Information:
This research was supported by a Grant from National Institute on Drug Abuse (Medications Development Division Contract No. 271-89-8159).

Keywords

  • Morphine analogs
  • Opiate receptors
  • Sulfate conjugates

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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