Universität zu Köln

Zarrad, Fadi, Zlatopolskiy, Boris D., Krapf, Philipp ORCID: 0000-0003-1671-2443, Zischler, Johannes ORCID: 0000-0003-3996-7473 and Neumaier, Bernd (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). BASEL: MDPI. ISSN 1420-3049

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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).

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Zarrad, Fadi UNSPECIFIED UNSPECIFIED UNSPECIFIED Zlatopolskiy, Boris D. UNSPECIFIED UNSPECIFIED UNSPECIFIED Krapf, Philipp UNSPECIFIED orcid.org/0000-0003-1671-2443 UNSPECIFIED Zischler, Johannes UNSPECIFIED orcid.org/0000-0003-3996-7473 UNSPECIFIED Neumaier, Bernd UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-208712
DOI:	10.3390/molecules22122231
Journal or Publication Title:	Molecules
Volume:	22
Number:	12
Date:	2017
Publisher:	MDPI
Place of Publication:	BASEL
ISSN:	1420-3049
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language COPPER-MEDIATED RADIOFLUORINATION; LATE-STAGE FLUORINATION; AUTOMATED SYNTHESIS; PARKINSONS-DISEASE; NEUROENDOCRINE TUMORS; IN-VITRO; PET; PALLADIUM; F-18; 3-O-METHYL-6-F-18-FLUORO-L-DOPA Multiple languages Biochemistry & Molecular Biology; Chemistry, Multidisciplinary Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/20871