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@ARTICLE{Grner:1014721,
author = {Gröner, Benedikt and Willmann, Michael and Donnerstag,
Lisa and Urusova, Elizaveta and Neumaier, Felix and Humpert,
Swen and Endepols, Heike and Neumaier, Bernd and
Zlatopolskiy, Boris D.},
title = {7-[18{F}]{F}luoro-8-azaisatoic {A}nhydrides: {V}ersatile
{P}rosthetic {G}roups for the {P}reparation of {PET}
{T}racers},
journal = {Journal of medicinal chemistry},
volume = {66},
number = {17},
issn = {0095-9065},
address = {Washington, DC},
publisher = {ACS},
reportid = {FZJ-2023-03411},
pages = {12629−12644},
year = {2023},
abstract = {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.},
cin = {INM-5},
ddc = {610},
cid = {I:(DE-Juel1)INM-5-20090406},
pnm = {5253 - Neuroimaging (POF4-525)},
pid = {G:(DE-HGF)POF4-5253},
typ = {PUB:(DE-HGF)16},
pubmed = {37625106},
UT = {WOS:001063590800001},
doi = {10.1021/acs.jmedchem.3c01310},
url = {https://juser.fz-juelich.de/record/1014721},
}