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

001     1014721
005     20240624130345.0
024 7 _ |a 10.1021/acs.jmedchem.3c01310
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024 7 _ |a 0022-2623
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024 7 _ |a 1520-4804
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024 7 _ |a 1943-2992
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024 7 _ |a 10.34734/FZJ-2023-03411
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024 7 _ |a 37625106
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082 _ _ |a 610
100 1 _ |a Gröner, Benedikt
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245 _ _ |a 7-[18F]Fluoro-8-azaisatoic Anhydrides: Versatile Prosthetic Groups for the Preparation of PET Tracers
260 _ _ |a Washington, DC
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520 _ _ |a 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.
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700 1 _ |a Willmann, Michael
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700 1 _ |a Donnerstag, Lisa
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700 1 _ |a Urusova, Elizaveta
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700 1 _ |a Neumaier, Felix
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700 1 _ |a Endepols, Heike
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700 1 _ |a Neumaier, Bernd
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700 1 _ |a Zlatopolskiy, Boris D.
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773 _ _ |a 10.1021/acs.jmedchem.3c01310
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