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Nucleophilic Synthesis of 6-l-[F]FDOPA. Is Copper-Mediated Radiofluorination the Answer?

Overview
Journal Molecules
Publisher MDPI
Specialty Biology
Date 2020 Sep 26
PMID 32977512
Citations 8
Authors
Affiliations
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Abstract

Positron emission tomography employing 6-l-[F]fluoro-3,4-dihydroxyphenylalanine (6-l-[F]FDOPA) is currently a highly relevant clinical tool for detection of gliomas, neuroendocrine tumors and evaluation of Parkinson's disease progression. Yet, the deficiencies of electrophilic synthesis of 6-l-[F]FDOPA hold back its wider use. To fulfill growing clinical demands for this radiotracer, novel synthetic strategies via direct nucleophilic F-radiloabeling starting from multi-Curie amounts of [F]fluoride, have been recently introduced. In particular, Cu-mediated radiofluorination of arylpinacol boronates and arylstannanes show significant promise for introduction into clinical practice. In this short review these current developments will be discussed with a focus on their applicability to automation.

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References
1.
Jacobson O, Kiesewetter D, Chen X . Fluorine-18 radiochemistry, labeling strategies and synthetic routes. Bioconjug Chem. 2014; 26(1):1-18. PMC: 4306521. DOI: 10.1021/bc500475e. View

2.
Mossine A, Tanzey S, Brooks A, Makaravage K, Ichiishi N, Miller J . One-pot synthesis of high molar activity 6-[F]fluoro-l-DOPA by Cu-mediated fluorination of a BPin precursor. Org Biomol Chem. 2019; 17(38):8701-8705. PMC: 6812483. DOI: 10.1039/c9ob01758e. View

3.
Libert L, Franci X, Plenevaux A, Ooi T, Maruoka K, Luxen A . Production at the Curie level of no-carrier-added 6-18F-fluoro-L-dopa. J Nucl Med. 2013; 54(7):1154-61. DOI: 10.2967/jnumed.112.112284. View

4.
Orlovskaya V, Modemann D, Kuznetsova O, Fedorova O, Urusova E, Kolks N . Alcohol-Supported Cu-Mediated F-Fluorination of Iodonium Salts under "Minimalist" Conditions. Molecules. 2019; 24(17). PMC: 6749259. DOI: 10.3390/molecules24173197. View

5.
Pretze M, Franck D, Kunkel F, Fosshag E, Wangler C, Wangler B . Evaluation of two nucleophilic syntheses routes for the automated synthesis of 6-[F]fluoro-l-DOPA. Nucl Med Biol. 2016; 45:35-42. DOI: 10.1016/j.nucmedbio.2016.10.007. View