This title appears in the Scientific Report :
2023
Please use the identifier:
http://dx.doi.org/10.1021/acs.jmedchem.3c01310 in citations.
Please use the identifier: http://dx.doi.org/10.34734/FZJ-2023-03411 in citations.
7-[18F]Fluoro-8-azaisatoic Anhydrides: Versatile Prosthetic Groups for the Preparation of PET Tracers
7-[18F]Fluoro-8-azaisatoic Anhydrides: Versatile Prosthetic Groups for the Preparation of PET Tracers
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...
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Personal Name(s): | Gröner, Benedikt |
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Willmann, Michael / Donnerstag, Lisa / Urusova, Elizaveta / Neumaier, Felix / Humpert, Swen / Endepols, Heike / Neumaier, Bernd (Corresponding author) / Zlatopolskiy, Boris D. | |
Contributing Institute: |
Nuklearchemie; INM-5 |
Published in: | Journal of medicinal chemistry, 66 (2023) 17, S. 12629−12644 |
Imprint: |
Washington, DC
ACS
2023
|
DOI: |
10.1021/acs.jmedchem.3c01310 |
DOI: |
10.34734/FZJ-2023-03411 |
Document Type: |
Journal Article |
Research Program: |
Neuroimaging |
Link: |
OpenAccess OpenAccess |
Publikationsportal JuSER |
Please use the identifier: http://dx.doi.org/10.34734/FZJ-2023-03411 in citations.
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. |