New radiolabelling chemistry: synthesis of phosphorus–[¹⁸F]fluorine compounds

Abstract

Abstract The feasibility of synthesizing compounds containing the P– 18 F bond has been demonstrated by labelling the pesticide, cholinesterase inhibitor Dimefox ( N , N , N ′ N ′‐tetramethylphosphorodiamidic fluoride) with F‐18. Radiolabelling was achieved in high radiochemical yield (96%) by nucleophilic substitution of the chloro group attached to phosphorus, in the oxidation state P(V), by 18 F − (activated with tetrabutylammonium carbonate in acetonitrile). Given the large number of important biological molecules possessing phosphorus such as oligonucleotides, phospholipids as well as phosphorylated proteins, sugars and steroids, this new labelling chemistry may provide an additional route to radiolabelling these biologically important compounds for use in PET. Copyright © 2005 John Wiley & Sons, Ltd.