Synthesis of the positron-emitting radiotracer [(18)F]-2-fluoro-2-deoxy-D-glucose from resin-bound perfluoroalkylsulfonates.
ABSTRACT A new approach to the synthesis of 2-fluoro-2-deoxy-d-glucose (FDG, [(19/18)F]-) is described, which employs supported perfluoroalkylsulfonate precursors , where the support consists of insoluble polystyrene resin beads. Treatment of these resins with [(19)F]fluoride ion afforded protected FDG [(19)F]- as the major product, and the identities of the main byproducts were determined. Acidic removal of the acetal protecting groups from [(19)F]- was shown to produce [(19)F]FDG. The method has been applied to the efficient radiosynthesis of the imaging agent [(18)F]FDG, and was shown to produce the radiochemical tracer in good radiochemical yield (average 73%, decay corrected).
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ABSTRACT: This review covers published literature describing the synthesis of labeled carbohydrates for use in molecular imaging, with a particular focus on the use of nuclear techniques (PET, SPECT). Recent advances in the radiosynthesis of [18F]FDG (electrophilic vs. nucleophilic radiofluorinations), a PET radiotracer based on glucose and the most widely PET tracer currently in use for cancer and inflammatory disease diagnosis, is considered. The powerful impact of [18F]FDG in the clinic has prompted intensive research efforts into glucose-based radiotracers for PET and SPECT imaging. These achievements are also reviewed, along with the use of glycopeptides for nuclear molecular imaging. Finally, recent work on the radionuclide labeling of nucleosides and glycoconjugates is discussed.European Journal of Organic Chemistry 03/2013; 2013(8). DOI:10.1002/ejoc.201201457 · 3.15 Impact Factor
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ABSTRACT: Microscale radiosynthesis of [F-18]FDG using a miniaturized device has been reported as a promising tool for positron emission tomography. However, small scale [F-18]FDG radiosynthesis on micro fluidic devices need to be studied further to evaluate its usefulness. This paper analyzes several micro-scale reactions of [F-18]FDG with various reaction conditions to achieve a higher radiochemical yield of [F-18]FDG. Synthesis of [F-18]FDG was carried out using mannose triflate on a microchip, and the crude product was purified via cartridge purification. The reaction conditions were optimized by examining several factors including reaction solvents, bases and their concentrations, that influence microscale radio synthesis of [F-18]FDG. Based on the investigation of several variables and their effects on the radio-synthetic reaction, [F-18]FDG was successfully synthesized on a micro-scale level with a radiochemical yield of 71% and within shorter time frame than that of the traditional method. Moreover, purity of the product was greater than 99%. These results show that the new guideline provides a more efficient and effective method of microscale [F-18]FDG radiosynthesis.Chemical Engineering Journal 12/2014; 258:62–68. DOI:10.1016/j.cej.2014.07.077 · 4.06 Impact Factor
Article: SolidPhase Nucleophilic Fluorination[Show abstract] [Hide abstract]
ABSTRACT: This study demonstrates solid-phase nucleophilic fluorination. Polymer-bound 1-phenoxy-2-sulfonyloxyethane, as a model compound, is converted to a fluorinated compound in a short time. Furthermore, this method is applied to synthesize a precursor of 2-deoxy-2-fluoro-D-glucose by solid-phase synthesis using a microwave oven.Synthetic Communications 06/2012; 42(12):1724-1730. DOI:10.1080/00397911.2010.535950 · 0.98 Impact Factor