Manufacturing 6-[<sup>18</sup>F]Fluoro-<i>L</i>-DOPA via Flow Chemistry-Enhanced Photoredox Radiofluorination

Wu, Xuedan; Chen, Wei; Deng, Huaifu; Wang, Li; Nicewicz, David A.; Li, Zibo; Wu, Zhanhong

doi:10.1021/acs.orglett.4c01114

Org. Lett.

2024

DOI: 10.1021/acs.orglett.4c01114

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Manufacturing 6-[¹⁸F]Fluoro-L-DOPA via Flow Chemistry-Enhanced Photoredox Radiofluorination

Xuedan Wu,

Wei Chen,

Huaifu Deng

et al.

Abstract: Detailed radiochemistry procedures, radiosynthesis setups, radiochemistry optimization and screening results, and quality control data (PDF)

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“…Precursor 1 was synthesized according to the previously reported method and characterized by 1 H NMR and 19 F NMR . The PRoBox was obtained from LED Radiofluidics Corp and was then connected to our automated module (model PET-MF-2 V-IT-I) . The automated synthesis of [ 18 F]FDOPA involves four steps: (1) azeotropic drying of 18 F-fluoride, (2) radiofluorination of 1 , (3) deprotection of the Boc-group and methyl-group, and (4) SPE purification.…”

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confidence: 99%

First-in-Human Evaluation of [¹⁸F]FDOPA Produced by Organo-Photoredox Reactions

Wang,

Lv,

Yang

et al. 2024

Bioconjugate Chem.

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Photoredox is a powerful synthetic tool in organic chemistry and has been widely used in various fields, including nuclear medicine and molecular imaging. In particular, acridinium-based organophotoredox radiolabeling has significantly impacted the production and discovery of positron emission tomography (PET) agents. Despite their extensive use in preclinical research, no PET agents synthesized by acridinium photoredox labeling have been tested in humans. [18F]FDOPA is clinically used for tumor diagnosis and the evaluation of neuropsychiatric disorders, but its application is limited by complex synthesis methods, the need for expensive modules, and/or the high cost of consumable materials/cassettes. In this report, we integrated a photoredox labeling unit with an automated module and produced [18F]FDOPA for human study. This research not only represents the first human study of a PET agent generated by acridinium-based organophotoredox reactions but also demonstrates the safety of this novel labeling method, serving as a milestone/reference for the clinical translation of other PET agents generated by this technique in the future.

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confidence: 99%

First-in-Human Evaluation of [¹⁸F]FDOPA Produced by Organo-Photoredox Reactions

Wang,

Lv,

Yang

et al. 2024

Bioconjugate Chem.

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Photoredox catalysis of acridinium and quinolinium ion derivatives

Fukuzumi,

Lee,

Nam

2024

Bulletin Korean Chem Soc

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Photoredox catalysis has attracted increasing attention because of wide range of synthetic transformations and solar energy conversion applications. Reviews on photoredox catalysis have so far focused predominantly on the synthetic applications. This review highlights how organic photoredox catalysts were developed and how they function as efficient photocatalysts in mechanistic point of views. In particular, 9‐mesityl‐10‐methylactidinium (Acr+–Mes) has been highlighted as one of the best organic photoredox catalysts. Acr+–Mes was originally developed as a model compound of the photosynthetic reaction center to mimic the long lifetime of the charge‐separated state in which the energy is converted to chemical energy in photosynthesis. The reason why Acr+–Mes acts as one of the most efficient photoredox catalyst is clarified in terms of the one‐electron redox potentials and long lifetimes of the electron‐transfer state (Acr•–Mes•+) produced upon photoexcitation of Acr+–Mes in different solvents. The reason why the mesityl substituent at the 9‐position of the Acr+ moiety is essential for the efficient photoredox catalysis is discussed in comparison with acridinium ions with different substituents R (Acr+–R) including 10‐methylacridinium ion with no substituent (AcrH+). The mechanisms of photoredox catalysis of Acr+–Mes are discussed in various synthetic transformations and solar energy conversion reactions mimicking photosynthesis. Photoredox catalysis of quinolinium ion and its derivatives is also discussed in comparison with that of Acr+–Mes. Finally, immobilization of Acr+–Mes and quinolinium ions to form the composite catalysts with redox catalyst is discussed to improve the photoredox catalytic activity and stability.

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Manufacturing 6-[¹⁸F]Fluoro-L-DOPA via Flow Chemistry-Enhanced Photoredox Radiofluorination

Abstract: Detailed radiochemistry procedures, radiosynthesis setups, radiochemistry optimization and screening results, and quality control data (PDF)

Cited by 2 publications

References 40 publications

First-in-Human Evaluation of [¹⁸F]FDOPA Produced by Organo-Photoredox Reactions

First-in-Human Evaluation of [¹⁸F]FDOPA Produced by Organo-Photoredox Reactions

Photoredox catalysis of acridinium and quinolinium ion derivatives

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Manufacturing 6-[18F]Fluoro-L-DOPA via Flow Chemistry-Enhanced Photoredox Radiofluorination

Abstract: Detailed radiochemistry procedures, radiosynthesis setups, radiochemistry optimization and screening results, and quality control data (PDF)

Cited by 2 publications

References 40 publications

First-in-Human Evaluation of [18F]FDOPA Produced by Organo-Photoredox Reactions

First-in-Human Evaluation of [18F]FDOPA Produced by Organo-Photoredox Reactions

Photoredox catalysis of acridinium and quinolinium ion derivatives

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Product

Resources

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Manufacturing 6-[¹⁸F]Fluoro-L-DOPA via Flow Chemistry-Enhanced Photoredox Radiofluorination

First-in-Human Evaluation of [¹⁸F]FDOPA Produced by Organo-Photoredox Reactions

First-in-Human Evaluation of [¹⁸F]FDOPA Produced by Organo-Photoredox Reactions