Universität zu Köln

Walter, Nils ORCID: 0000-0003-3727-3750, Bertram, Jan, Drewes, Birte ORCID: 0000-0002-6849-1438, Bahutski, Victor, Timmer, Marco, Schuetz, Markus B., Kraemer, Felicia, Neumaier, Felix, Endepols, Heike, Neumaier, Bernd and Zlatopolskiy, Boris D. (2022). Convenient PET-tracer production via SuFEx F-18-fluorination of nanomolar precursor amounts. Eur. J. Med. Chem., 237. ISSY-LES-MOULINEAUX: ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER. ISSN 1768-3254

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Abstract

Recently, a protocol for radiolabeling of aryl fluorosulfates ( SuFEx click radiolabeling ) using ultrafast F-18/F-19 isotopic exchange has been reported. Although promising, the original procedure turned out to be rather inefficient. However, systematic optimization of the reaction parameters allowed for development of a robust method for SuFEx radiolabeling which obviates the need for azeotropic drying, base addition and HPLC purification. The developed protocol enabled efficient F-18-fluorination of low nanomolar amounts of aryl fluorosulfates in highly diluted solution (micromolar concentrations). It was successfully used to prepare a series of 29 F-18-fluorosulfurylated phenols -including modified ezetimibe, alpha- tocopherol and etoposide, the two tyrosine derivatives Boc-Tyr([F-18]FS)-OMe and H-Tyr([F-18]FS)-OMe, the FAP-specific ligand [F-18]FS-UAMC1110, and the DPA-714 analog [F-18]FS-DPA -in fair to excellent yields. Preliminary evaluation demonstrated sufficient in vivo stability of radiofluorinated electron rich or neutral {Boc-Tyr([F-18]FS)-OMe), H-Tyr([F-18]FS)-OMe and [F-18]FS-DPA} aryl fluorosulfates. Furthermore, [F-18]FS-DPA was identified as a promising tracer for visualization of TSPO expression.(c) 2022 Elsevier Masson SAS. All rights reserved.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Walter, Nils UNSPECIFIED orcid.org/0000-0003-3727-3750 UNSPECIFIED Bertram, Jan UNSPECIFIED UNSPECIFIED UNSPECIFIED Drewes, Birte UNSPECIFIED orcid.org/0000-0002-6849-1438 UNSPECIFIED Bahutski, Victor UNSPECIFIED UNSPECIFIED UNSPECIFIED Timmer, Marco UNSPECIFIED UNSPECIFIED UNSPECIFIED Schuetz, Markus B. UNSPECIFIED UNSPECIFIED UNSPECIFIED Kraemer, Felicia UNSPECIFIED UNSPECIFIED UNSPECIFIED Neumaier, Felix UNSPECIFIED UNSPECIFIED UNSPECIFIED Endepols, Heike UNSPECIFIED UNSPECIFIED UNSPECIFIED Neumaier, Bernd UNSPECIFIED UNSPECIFIED UNSPECIFIED Zlatopolskiy, Boris D. UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-675501
DOI:	10.1016/j.ejmech.2022.114383
Journal or Publication Title:	Eur. J. Med. Chem.
Volume:	237
Date:	2022
Publisher:	ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER
Place of Publication:	ISSY-LES-MOULINEAUX
ISSN:	1768-3254
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language POSITRON-EMISSION-TOMOGRAPHY; AROMATIC-AMINO-ACIDS; METABOLISM; CHEMISTRY Multiple languages Chemistry, Medicinal Multiple languages
URI:	http://kups.ub.uni-koeln.de/id/eprint/67550