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

doi:10.1016/j.bmcl.2006.05.060

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 journal › Article › peer-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 language	English
Pages (from-to)	4291-4295
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	16
Issue number	16
DOIs	https://doi.org/10.1016/j.bmcl.2006.05.060
State	Published - 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).

Funding

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

Funders	Funder number
National Institute on Drug Abuse	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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10.1016/j.bmcl.2006.05.060

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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.",

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AU - Crooks, Peter A.

AU - Kottayil, Santosh G.

AU - Al-Ghananeem, Abeer M.

AU - Byrn, Stephen R.

AU - Allan Butterfield, D.

N1 - Funding Information: This research was supported by a Grant from National Institute on Drug Abuse (Medications Development Division Contract No. 271-89-8159).

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AB - 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.

KW - Morphine analogs

KW - Opiate receptors

KW - Sulfate conjugates

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

Abstract

Bibliographical note

Funding

Keywords

ASJC Scopus subject areas

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