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

University of Kentucky
Purdue University

Research output: Contribution to journal › Article › peer-review

29 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 - 15 Aug 2006
Externally published	Yes

Keywords

Morphine analogs
Opiate receptors
Sulfate conjugates

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10.1016/j.bmcl.2006.05.060

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

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.",

keywords = "Morphine analogs, Opiate receptors, Sulfate conjugates",

author = "Crooks, \{Peter A.\} and Kottayil, \{Santosh G.\} and Al-Ghananeem, \{Abeer M.\} and Byrn, \{Stephen R.\} and \{Allan Butterfield\}, D.",

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doi = "10.1016/j.bmcl.2006.05.060",

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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.

PY - 2006/8/15

Y1 - 2006/8/15

N2 - 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.

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

UR - https://www.scopus.com/pages/publications/33745713206

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DO - 10.1016/j.bmcl.2006.05.060

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AN - SCOPUS:33745713206

SN - 0960-894X

VL - 16

SP - 4291

EP - 4295

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 16

ER -

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

Abstract

Keywords

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