F-18 labeling of ether-linked analogs of diacylglycerol

Article abstract of DOI:10.1002/(SICI)1099-1344(199903)42:3<245::AID-JLCR184>3.0.CO;2-G

Ether-linked analogs of fluorine-18 labeled diacylglycerol were synthesized in order to improve their bioavailability in vivo. Compounds were designed to have long chain (having sixteen carbons) alkyl substituent on 1-O-position and short alkyl or acyl group (eight carbons) on 2-O-position of glycerol. Introduction of ¹⁸F into each chain resulted in four labeled tracers. Precursors having tosyloxy or bromo moiety as leaving group were obtained step wise alkylations and/or acylations of 3-O-benzylglycerol. Nucleophilic radiofluorination of the precursors thus obtained gave labeled intermediates in up to 40% radiochemical yield. Ether-linked diacylglycerol analogs were afforded through their deprotection with H₂ and Pd/C. Catalytic transfer hydrogenation was also attempted, however, insufficient result was achieved in spite of its usefulness as labeling procedure.