Reference : Production at the Curie Level of No-Carrier-Added 6-18F-Fluoro-L-Dopa
Scientific journals : Article
Physical, chemical, mathematical & earth Sciences : Chemistry
Production at the Curie Level of No-Carrier-Added 6-18F-Fluoro-L-Dopa
Libert, Lionel mailto [Université de Liège - ULiège > > > Doct. sc. (chimie - Bologne)]
Franci, Xavier []
Plenevaux, Alain mailto [Université de Liège - ULiège > > Centre de recherches du cyclotron >]
OOi, Takashi mailto []
Maruoka, Keiji mailto []
Luxen, André mailto [Université de Liège - ULiège > Département de chimie (sciences) > Chimie organique de synthèse >]
Lemaire, Christian mailto [Université de Liège - ULiège > > Centre de recherches du cyclotron >]
Journal of Nuclear Medicine
Society of Nuclear Medicine
Yes (verified by ORBi)
[en] 18F-FDOPA ; 18F-Fluoride ; enantioselective ; SPE ; phase-transfer catalysis
[en] 6-18F-fluoro-L-dopa (18F-FDOPA) has proven to be a useful radiopharmaceutical for the evaluation of presynaptic dopaminergic function using PET. In comparison to electrophilic synthesis, the no-carrier-added (NCA) nucleophilic method has several advantages.
These include much higher available activity and specific activity. Recently, we have described an NCA enantioselective synthesis using a chiral phase-transfer catalyst. However, some chemicals were difficult to implement into a commercially available synthesizer, restricting access to this radiopharmaceutical to only a few PET centers. Methods: In this paper, 2 important chemical improvements are proposed to simplify production of 18F-FDOPA, resulting in straightforward automation of the synthesis in a commercially available module. Results: First, a fast, simple, and reliable synthesis of 2-18F-fluoro-4,5-dimethoxybenzyl iodide on a solid phase support was developed. Second, a phase-transfer catalyst alkylation of a glycine derivative at room temperature was used to enable enantioselective carbon–carbon bond formation. After hydrolysis and high-performance liquid chromatography purification, a high enantiomeric excess of 18F-FDOPA (~97%) was obtained using a chiral catalyst available from a biphenyl 3 substrate. The total synthesis time was 63 min, and the decay-corrected radiochemical yield was 36% +/- 3% (n = 8). Conclusion: By exploiting the advantages of this NCA approach, using a starting activity of 185 GBq of NCA 18F-fluoride, high activities of 18F-FDOPA (> 45 GBq) with high specific activity (>753 GBq/mmol) are now available at the end of synthesis for use in clinical investigations.
Centre de Recherches du Cyclotron - CRC

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