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001014721 1001_ $$0P:(DE-Juel1)180812$$aGröner, Benedikt$$b0
001014721 245__ $$a7-[18F]Fluoro-8-azaisatoic Anhydrides: Versatile Prosthetic Groups for the Preparation of PET Tracers
001014721 260__ $$aWashington, DC$$bACS$$c2023
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001014721 520__ $$a18F-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.
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001014721 7001_ $$0P:(DE-Juel1)173964$$aWillmann, Michael$$b1
001014721 7001_ $$0P:(DE-HGF)0$$aDonnerstag, Lisa$$b2
001014721 7001_ $$0P:(DE-Juel1)176705$$aUrusova, Elizaveta$$b3$$ufzj
001014721 7001_ $$0P:(DE-Juel1)175142$$aNeumaier, Felix$$b4
001014721 7001_ $$0P:(DE-Juel1)132740$$aHumpert, Swen$$b5$$ufzj
001014721 7001_ $$0P:(DE-Juel1)180330$$aEndepols, Heike$$b6$$ufzj
001014721 7001_ $$0P:(DE-Juel1)166419$$aNeumaier, Bernd$$b7$$eCorresponding author
001014721 7001_ $$0P:(DE-Juel1)176188$$aZlatopolskiy, Boris D.$$b8
001014721 773__ $$0PERI:(DE-600)1491411-6$$a10.1021/acs.jmedchem.3c01310$$gp. acs.jmedchem.3c01310$$n17$$p12629−12644$$tJournal of medicinal chemistry$$v66$$x0095-9065$$y2023
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