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@ARTICLE{Kramer:180487,
author = {C. S. Kramer$^*$ and L. Greiner$^*$ and K. Kopka and M.
Schäfer$^*$},
title = {{F}luorination of silyl prosthetic groups by fluorine
mediated silyl ether linker cleavage: a concept study with
conditions applicable in radiofluorination.},
journal = {EJNMMI radiopharmacy and chemistry},
volume = {7},
number = {1},
issn = {2365-421X},
address = {[Heidelberg]},
publisher = {SpringerOpen},
reportid = {DKFZ-2022-01366},
pages = {15},
year = {2022},
note = {#EA:E030#LA:E030#},
abstract = {Positron emission tomography (PET) is a powerful tool in
medical imaging, especially in combination with the PET
radionuclide fluorine-18 that possesses optimal
characteristics. For labelling of biomolecules and
low-molecular weight tracers, fluorine-18 can be covalently
bound to silicon by either nucleophilic replacements of
leaving groups (like ethers) or by isotope exchange of
fluorine-19. While nucleophilic substitutions require
additional purification steps for the removal of
contaminants, isotope exchange with fluorine-18 results in
low molar activity. Both challenges can be addressed with a
detagging-fluorination of an immobilized silyl ether
motif.By overcoming the susceptibility towards hydrolysis,
optimized detagging conditions (improved reaction time,
fluorination reagent, linker, and resin) could afford the
highly sterically hindered silyl fluoride motifs, that are
commonly applied in radiochemistry in small and
semipreparative scales. The described reaction conditions
with fluorine-19 are transferrable to conditions with
[18F]fluoride and silyl fluorides were obtained after
approx. 10 min reaction time and in high-purity after
mechanical filtration.We present a proof-of-concept study
for a detagging-fluorination of two silyl ethers that are
bound to an optimized amino alcohol resin. We show with our
model substrate that our solid-phase linker combination is
capable of yielding the desired silicon fluoride in amounts
sufficient for biological studies in animals or humans under
standard fluorination conditions that may also be
transferred to a radiolabelling setting. In conclusion, our
presented approach could optimize the molar activity and
simplify the preparation of radiofluorinated silyl
fluorides.},
keywords = {Detagging (Other) / Fluorine-18 (Other) / PET (Other) /
Radiofluorination (Other) / SiFA (Other) / Silyl fluorides
(Other) / Solid phase synthesis (Other) / Solid support
(Other)},
cin = {E030},
ddc = {610},
cid = {I:(DE-He78)E030-20160331},
pnm = {315 - Bildgebung und Radioonkologie (POF4-315)},
pid = {G:(DE-HGF)POF4-315},
typ = {PUB:(DE-HGF)16},
pubmed = {pmid:35751707},
doi = {10.1186/s41181-022-00167-y},
url = {https://inrepo02.dkfz.de/record/180487},
}