Synthesis of (E)-5-(2-radioiodovinyl)arabinosyl uridine analog for probing HSV-1 thymidine kinase gene

Abstract

The genetic probe labeled with positron emitter for monitoring tumor cells transfacted by herpes simplex virus thymidine kinase gene has been intensively studied. A useful synthetic methodology was developed to synthesize (E)-5-[2-(tributylstannyl)vinyl]arabinosyl uridine (TSVAU) and to radiolabel (E)-5-{2-[125I]iodovinyl}arabinosyl uridine (IVAU) substrate for herpes simplex virus type-1 thymidine kinase gene. The synthesis started from arabinosyl uridine via six steps to provide TSVAU in 18% yield. The subsequent radiolabeling with Na-[125I]I under oxidation provided [ 125I]IVAU in 80% radiochemical yield. Copyright © 2005 The Chemical Society of Japan.