18F-Labeled azaisatoic anhydrides as versatile prosthetic groups for indirect radiofluorination

Abstract

To enable ¹⁸F-labeling of sensitive molecules under mild conditions, 1-alkylamino-7-[¹⁸F]fluoro-8-azaisatoic anhydrides ([¹⁸F]AFAs) were developed as new prosthetic groups for indirect radiofluorination. The [¹⁸F]AFAs were efficiently prepared within 15 min using readily accessible precursors and could be conjugated with a range of amines and alkyne- or azide-functionalized precursors to afford the corresponding ¹⁸F-labeled conjugates in high radiochemical conversions of up to 98%. The practical utility of the new prosthetic groups was confirmed by successful radiosynthesis of three ¹⁸F-labeled PSMA ligands with excellent in vivo stability and, in one case, promising imaging properties.

Gröner, B.; Willmann, M.; Donnerstag, L.; Urusova, E.; Neumaier, F.; Humpert, S.; Endepols, H.; Neumaier, B.; Zlatopolskiy, B. D.

7-[¹⁸F]Fluoro-8-azaisatoic Anhydrides: Versatile Prosthetic Groups for the Preparation of PET Tracers

Journal of medicinal chemistry 2023, 66 (17), 12629-12644.