Prostaglandin photoaffinity probes: synthesis and binding affinity of aryl azide-substituted C-1 esters of prostaglandin F2 alpha.
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.
Golinski
M
M
Department of Chemistry, University of Kentucky, Lexington 40506.
Heine
M
M
Orlicky
D J
DJ
Fitz
T A
TA
Watt
D S
DS
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
D000345:Affinity Labels; D001386:Azides; D004952:Esters; D005461:Fluorine; D015237:Dinoprost