Bioorganic & Medicinal Chemistry Letters 2006-08-15

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

Index: Bioorg. Med. Chem. Lett. 16(16) , 4291-5, (2006)

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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 mu-, delta-, kappa(1)-, kappa(2)-, and kappa(3)-opiate receptors. Several compounds exhibited good affinity for the mu-opiate receptor. Morphine-3-O-propionyl-6-O-sulfate had four times greater affinity than morphine at the mu-opiate receptor and was the most selective compound at this receptor subtype.