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 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.
authors.affiliation: Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, 40536-0082, USA. pcrooks@email.uky.edu
authors.forename: Peter A
authors.initials: PA
authors.lastname: Crooks
authors.forename: Santosh G
authors.initials: SG
authors.lastname: Kottayil
authors.forename: Abeer M
authors.initials: AM
authors.lastname: Al-Ghananeem
authors.forename: Stephen R
authors.initials: SR
authors.lastname: Byrn
authors.forename: D Allan
authors.initials: DA
authors.lastname: Butterfield
mesh_terms: 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*
chemical_list: D004952:Esters; D008024:Ligands; D013431:Sulfates; D009020:Morphine; D004090:Dihydromorphine; D003061:Codeine