Universität zu Köln

Modemann, Daniel J., Zlatopolskiy, Boris D., Urusova, Elizaveta A., Zischler, Johannes, Craig, Austin, Ermert, Johannes ORCID: 0000-0002-2561-7766, Guliyev, Mehrab, Endepols, Heike ORCID: 0000-0002-6166-4818 and Neumaier, Bernd ORCID: 0000-0001-5425-3116 (2019). 2-[F-18] Fluorophenylalanine: Synthesis by Nucleophilic F-18-Fluorination and Preliminary Biological Evaluation. Synthesis, 51 (3). S. 664 - 677. STUTTGART: GEORG THIEME VERLAG KG. ISSN 1437-210X

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Abstract

2-[F-18]Fluorophenylalanine (2-[F-18]FPhe), a promising PET tracer for imaging of cerebral infarction and tumors, was efficiently prepared from an easily accessible iodonium salt precursor using Cu-mediated radiofluorination under 'low base' or 'minimalist' conditions. Whereas significant racemization was initially observed if the 'minimalist' protocol was applied for radiolabeling, it was completely suppressed by the careful adjustment of F-18(-) preprocessing. The initial biological study revealed a higher uptake of 2-[F-18]FPhe in different tumor cells in comparison to that of [F-18]FET. In contrast to 4-[F-18]FPhe, which suffered from rapid defluorination in vivo, 2-[F-18]FPhe demonstrated a sufficient in vivo stability. Conclusively, 2-[F-18]FPhe is a promising PET probe that is now readily available using Cu-mediated radiofluorination under 'minimalist' or 'low base' conditions. The simplicity of the translation of the proposed procedures to automated synthesis modules allows a broad biological evaluation of 2-[F-18]FPhe. Notably, a novel protocol for the preparation of N-Boc protected amino acids from the respective Ni-Schiff base complexes was developed that avoided application of strongly acidic conditions.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Modemann, Daniel J. UNSPECIFIED UNSPECIFIED UNSPECIFIED Zlatopolskiy, Boris D. UNSPECIFIED UNSPECIFIED UNSPECIFIED Urusova, Elizaveta A. UNSPECIFIED UNSPECIFIED UNSPECIFIED Zischler, Johannes UNSPECIFIED UNSPECIFIED UNSPECIFIED Craig, Austin UNSPECIFIED UNSPECIFIED UNSPECIFIED Ermert, Johannes UNSPECIFIED orcid.org/0000-0002-2561-7766 UNSPECIFIED Guliyev, Mehrab UNSPECIFIED UNSPECIFIED UNSPECIFIED Endepols, Heike UNSPECIFIED orcid.org/0000-0002-6166-4818 UNSPECIFIED Neumaier, Bernd UNSPECIFIED orcid.org/0000-0001-5425-3116 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-158517
DOI:	10.1055/s-0037-1611370
Journal or Publication Title:	Synthesis
Volume:	51
Number:	3
Page Range:	S. 664 - 677
Date:	2019
Publisher:	GEORG THIEME VERLAG KG
Place of Publication:	STUTTGART
ISSN:	1437-210X
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language ALPHA-AMINO-ACIDS; ASYMMETRIC-SYNTHESIS; NI(II) COMPLEXES; ADDITION-REACTIONS; HOMOLOGATION; TRANSPORT; PET; RADIOFLUORINATION; ESTERS; BASES Multiple languages Chemistry, Organic Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/15851