5'-Fluorosulfonylbenzoyl derivatives of therapeutic nucleoside analogs

Several fluorosulfonylbenzoyl /FSB/ purine and pyrimidine nucleoside analogs of the clinically useful antimetabolites which belong to endo affinity labeling compounds were synthetized. Structures were confirmed by both 1H NMR and UV spectroscopy and by elemental analysis. Procedure for preparation of microamount of [3H] FSB-araC was developed. Bonding of radioactive FSB-araC to nucleotide utilizing enzymes in K562 myeloblasts soluble protein extract was compared with araCTP-degradating activities in this extract after DEAE-cellulose column chromatography. There was found that five major peaks of the radioactivity bound to the protein coincident with peaks of araCTP degradation. Bonding of [3H] FSB-araC in CCRF-CEM lymphoblasts exhibits only 3 major peaks of the bound radioactivity. This result correlates with the higher sensitivity of the CEM cells to araC.