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Volume 22
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10.3390/molecules22122231
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Article

A Practical Method for the Preparation of 18F-Labeled Aromatic Amino Acids from Nucleophilic [18F]Fluoride and Stannyl Precursors for Electrophilic Radiohalogenation

by
Fadi Zarrad
1,2,
Boris D. Zlatopolskiy
1,2,3,*,
Philipp Krapf
1,2,
Johannes Zischler
1,2 and
Bernd Neumaier
1,2,3,*
1
Institute of Neuroscience and Medicine, Nuclear Chemistry (INM-5), Forschungszentrum Jülich GmbH, 52428 Jülich, Germany
2
Institute of Radiochemistry and Experimental Molecular Imaging, University Clinic Cologne, 50931 Cologne, Germany
3
Max Planck Institute for Metabolism Research, Cologne 50931, Germany
*
Authors to whom correspondence should be addressed.
Molecules 2017, 22(12), 2231; https://doi.org/10.3390/molecules22122231
Submission received: 6 November 2017 / Revised: 5 December 2017 / Accepted: 12 December 2017 / Published: 15 December 2017
(This article belongs to the Section Medicinal Chemistry)
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Abstract

In a recent contribution of Scott et al., the substrate scope of Cu-mediated nucleophilic radiofluorination with [18F]KF for the preparation of 18F-labeled arenes was extended to aryl- and vinylstannanes. Based on these findings, the potential of this reaction for the production of clinically relevant positron emission tomography (PET) tracers was investigated. To this end, Cu-mediated radiofluorodestannylation using trimethyl(phenyl)tin as a model substrate was re-evaluated with respect to different reaction parameters. The resulting labeling protocol was applied for 18F-fluorination of different electron-rich, -neutral and -poor arylstannyl substrates in RCCs of 16–88%. Furthermore, this method was utilized for the synthesis of 18F-labeled aromatic amino acids from additionally N-Boc protected commercially available stannyl precursors routinely applied for electrophilic radiohalogenation. Finally, an automated synthesis of 6-[18F]fluoro-l-m-tyrosine (6-[18F]FMT), 2-[18F]fluoro-l-tyrosine (2-[18F]F-Tyr), 6-[18F]fluoro-l-3,4-dihydroxyphenylalanine (6-[18F]FDOPA) and 3-O-methyl-6-[18F]FDOPA ([18F]OMFD) was established furnishing these PET probes in isolated radiochemical yields (RCYs) of 32–54% on a preparative scale. Remarkably, the automated radiosynthesis of 6-[18F]FDOPA afforded an exceptionally high RCY of 54 ± 5% (n = 5).
Keywords: 18F; radiofluorination; destannylation; positron emission tomography 18F; radiofluorination; destannylation; positron emission tomography
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MDPI and ACS Style

Zarrad, F.; Zlatopolskiy, B.D.; Krapf, P.; Zischler, J.; Neumaier, B. A Practical Method for the Preparation of 18F-Labeled Aromatic Amino Acids from Nucleophilic [18F]Fluoride and Stannyl Precursors for Electrophilic Radiohalogenation. Molecules 2017, 22, 2231. https://doi.org/10.3390/molecules22122231

AMA Style

Zarrad F, Zlatopolskiy BD, Krapf P, Zischler J, Neumaier B. A Practical Method for the Preparation of 18F-Labeled Aromatic Amino Acids from Nucleophilic [18F]Fluoride and Stannyl Precursors for Electrophilic Radiohalogenation. Molecules. 2017; 22(12):2231. https://doi.org/10.3390/molecules22122231

Chicago/Turabian Style

Zarrad, Fadi, Boris D. Zlatopolskiy, Philipp Krapf, Johannes Zischler, and Bernd Neumaier. 2017. "A Practical Method for the Preparation of 18F-Labeled Aromatic Amino Acids from Nucleophilic [18F]Fluoride and Stannyl Precursors for Electrophilic Radiohalogenation" Molecules 22, no. 12: 2231. https://doi.org/10.3390/molecules22122231

APA Style

Zarrad, F., Zlatopolskiy, B. D., Krapf, P., Zischler, J., & Neumaier, B. (2017). A Practical Method for the Preparation of 18F-Labeled Aromatic Amino Acids from Nucleophilic [18F]Fluoride and Stannyl Precursors for Electrophilic Radiohalogenation. Molecules, 22(12), 2231. https://doi.org/10.3390/molecules22122231

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