Opiate receptor binding properties of morphine-, dihydromorphine-, and codeine 6-O-sulfate ester congeners.
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.
Crooks
Peter A
PA
Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, 40536-0082, USA. pcrooks@email.uky.edu
Kottayil
Santosh G
SG
Al-Ghananeem
Abeer M
AM
Byrn
Stephen R
SR
Butterfield
D Allan
DA
D000818:Animals; D003061:Codeine / Q000737:chemistry*; D004090:Dihydromorphine / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D006168:Guinea Pigs; D020128:Inhibitory Concentration 50; D007700:Kinetics; D008024:Ligands; D008956:Models, Chemical; D009020:Morphine / Q000737:chemistry*; D011485:Protein Binding; D013431:Sulfates / Q000737:chemistry*
D004952:Esters; D008024:Ligands; D013431:Sulfates; D009020:Morphine; D004090:Dihydromorphine; D003061:Codeine