%0 Journal Article
%A Gröner, Benedikt
%A Willmann, Michael
%A Donnerstag, Lisa
%A Urusova, Elizaveta
%A Neumaier, Felix
%A Humpert, Swen
%A Endepols, Heike
%A Neumaier, Bernd
%A Zlatopolskiy, Boris D.
%T 7-[18F]Fluoro-8-azaisatoic Anhydrides: Versatile Prosthetic Groups for the Preparation of PET Tracers
%J Journal of medicinal chemistry
%V 66
%N 17
%@ 0095-9065
%C Washington, DC
%I ACS
%M FZJ-2023-03411
%P 12629−12644
%D 2023
%X 18F-Fluorination of sensitive molecules is often challenging, but can be accomplished under suitably mild conditions using radiofluorinated prosthetic groups (PGs). Herein, 1-alkylamino-7-[18F]fluoro-8-azaisatoic anhydrides ([18F]AFAs) are introduced as versatile 18F-labeled building blocks that can be used as amine-reactive or “click chemistry” PGs. [18F]AFAs were efficiently prepared within 15 min by “on cartridge” radiolabeling of readily accessible trimethylammonium precursors. Conjugation with a range of amines afforded the corresponding 2-alkylamino-6-[18F]fluoronicotinamides in radiochemical conversions (RCCs) of 15−98%. In addition, radiolabeling of alkyne- or azide-functionalized precursors with azidopropyl- or propargyl-substituted [18F]AFAs using Cu-catalyzed click cycloaddition afforded the corresponding conjugates in RCCs of 44−88%. The practical utility of the PGs was confirmed by the preparation of three 18F-labeled PSMA ligands in radiochemical yields of 28−42%. Biological evaluation in rats demonstrated excellent in vivo stability of all three conjugates. In addition, one conjugate ([18F]JK-PSMA-15) showed favorable imaging properties for high-contrast visualization of small PSMA-positive lesions.
%F PUB:(DE-HGF)16
%9 Journal Article
%$ 37625106
%U <Go to ISI:>//WOS:001063590800001
%R 10.1021/acs.jmedchem.3c01310
%U https://juser.fz-juelich.de/record/1014721