A solid-phase route to (18)F-labeled tracers, exemplified by the synthesis of [(18)F]2-fluoro-2-deoxy-D-glucose

Brown, Lynda J., Bouvet, Denis R., Champion, Sue, Gibson, Alex M., Hu, Yulai, Jackson, Alex, Khan, Imtiaz, Ma, Nianchun, Millot, Nicholas, Wadsworth, Harry and Brown, Richard C.D. (2007) A solid-phase route to (18)F-labeled tracers, exemplified by the synthesis of [(18)F]2-fluoro-2-deoxy-D-glucose. Angewandte Chemie International Edition, 46 (6), 941-944. (doi:10.1002/anie.200603394). (PMID:17183499)

Abstract

Due to the short half-life of [18F] (half-life = 110min), the synthesis and purification ofradiotracers incorporating this positron-emitting radionuclide needs to be carried out as rapidly aspossible for applications in imaging using positron emission tomography (PET). Here we describe a conceptually new strategy for the synthesis of [18F]-containing molecules, which releases theradiotracer from a solid-supported precursor using limiting [18F]-fluoride. A major advantage overexisting solution methods lies in the fact that incorporation of the radionuclide occurs by means of nucleophilic displacement of a sulfonate ester linkage to the solid-phase, which occurs withconcomitant release of the radiotracer into solution. The vast excess of precursor that istraditionally employed remains attached to the solid-phase and is removed by simple filtration. The potential of the methodology is illustrated by the synthesis of the most important and widelyused [18F]-radiotracer 2-[18F]-fluoro-2-deoxyglucose (FDG) with good radiochemical yield (73%,decay corrected) and superior chemical purity.

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Contributors

Author: Lynda J. Brown

Author: Richard C.D. Brown

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