title: Prostaglandin photoaffinity probes: synthesis and binding affinity of aryl azide-substituted C-1 esters of prostaglandin F2 alpha.
abstract: In seeking prostaglandin F2 alpha (PGF2 alpha) photoaffinity probes possessing both an efficient, photoactive cross-linking substituent and a radiolabel of high specific activity, the synthesis and binding affinity of PGF2 alpha C-1 esters in which the alcohol component possessed either an aryl azide or a perfluorinated aryl azide was investigated. These derivatives showed great promise due to their ability to compete for the binding of [3H]-PGF2 alpha in both a luteal membrane binding assay and in a whole luteal cell binding assay. Identification of the C-1 site in PGF2 alpha as a site for modification of the PGF2 alpha molecule with photoactive alcohol derivatives represented a logical step toward the goal of developing a useful PGF2 alpha photoaffinity probe.
authors.affiliation: Department of Chemistry, University of Kentucky, Lexington 40506.
authors.forename: M
authors.initials: M
authors.lastname: Golinski
authors.forename: M
authors.initials: M
authors.lastname: Heine
authors.forename: D J
authors.initials: DJ
authors.lastname: Orlicky
authors.forename: T A
authors.initials: TA
authors.lastname: Fitz
authors.forename: D S
authors.initials: DS
authors.lastname: Watt
mesh_terms: D000345:Affinity Labels / Q000138:chemical synthesis* / Q000378:metabolism; D000818:Animals; D001386:Azides / Q000737:chemistry*; D001667:Binding, Competitive; D002417:Cattle; D003338:Corpus Luteum / Q000378:metabolism; D015237:Dinoprost / Q000737:chemistry* / Q000378:metabolism; D004952:Esters / Q000138:chemical synthesis / Q000378:metabolism; D005260:Female; D005461:Fluorine / Q000737:chemistry*; D008184:Luteal Cells / Q000378:metabolism; D015394:Molecular Structure; D010777:Photochemistry; D012756:Sheep
chemical_list: D000345:Affinity Labels; D001386:Azides; D004952:Esters; D005461:Fluorine; D015237:Dinoprost