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: 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
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ABSTRACT: A Resin-linker-vector (RLV) strategy is described for the radiosynthesis of tracer molecules containing the radionuclide (18) F, which releases the labelled vector into solution upon nucleophilic substitution of a polystyrene-bound arylsulfonate linker with [(18) F]-fluoride ion. Three model linker-vector molecules 7 a-c containing different alkyl spacer groups were assembled in solution from (4-chlorosulfonylphenyl)alkanoate esters, exploiting a lipase-catalysed chemoselective carboxylic ester hydrolysis in the presence of the sulfonate ester as a key step. The linker-vector systems were attached to aminomethyl polystyrene resin through amide bond formation to give RLVs 8 a-c with acetate, butyrate and hexanoate spacers, which were characterised by using magic-angle spinning (MAS) NMR spectroscopy. On fluoridolysis, the RLVs 8 a, b containing the longer spacers were shown to be more effective in the release of the fluorinated model vector (4-fluorobutyl)phenylcarbamic acid tert-butyl ester (9) in NMR kinetic studies and gave superior radiochemical yields (RCY≈60 %) of the (18) F-labelled vector. The approach was applied to the synthesis of the radiopharmaceutical O-(2-[(18) F]-fluoroethyl)-L-tyrosine ([(18) F]-FET), delivering protected [(18) F]-FET in >90 % RCY. Acid deprotection gave [(18) F]-FET in an overall RCY of 41 % from the RLV.Chemistry - A European Journal 01/2013; 19(5). DOI:10.1002/chem.201202474 · 5.70 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