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@ARTICLE{Kramer:274564,
author = {C. S. Kramer$^*$ and T. Kanagasundaram$^*$ and J.
Matthias$^*$ and K. Kopka$^*$},
title = {{E}fforts toward {PET}-{A}ctivatable {R}ed-{S}hifted
{S}ilicon {R}hodamines and {S}ilicon {P}yronine {D}yes},
journal = {Pharmaceuticals},
volume = {16},
number = {3},
issn = {1424-8247},
address = {Basel},
publisher = {MDPI},
reportid = {DKFZ-2023-00641},
pages = {401},
year = {2023},
note = {#EA:E030#LA:E030#},
abstract = {Tracers for bimodal optical imaging and positron emission
tomography unite multipleadvantages in a single molecule.
Their tumor-specific uptake can be visualized after their
PETactivation by radiofluorination via PET/CT or PET/MRI
allowing for staging or therapy planning,while their
non-radioactive moiety additionally facilitates the
visualization of malignant tissueduring intraoperative
fluorescence-guided surgery or in histological assessments.
The silicon-bridgedxanthene core offers the opportunity for
radiofluorination with SiFA isotope exchange to obtaina
small-molecule, PET-activatable NIR dye that can be linked
to different target vectors. Herein,we demonstrate for the
first time the PET-activation of a fluorinated silicon
pyronine, belongingto a class of low-molecular-weight
fluorescence dyes with a large Stokes shift (up to 129 nm)
andsolvent-dependent NIR dye properties, with a successful
radiochemical conversion of $70\%.$ Thenon-fluorinated
pyronine precursor is easily accessible by a three-step
sequence from commerciallystarting material with a $12\%$
overall yield. Moreover, a library of seven unusually
functionalized(by approximately 15 nm), red-shifted silicon
rhodamines were synthesized in three- to four-stepsequences
and the optical properties of the novel dyes were
characterized. It was also shownthat the synthesized silicon
rhodamine dyes can be easily conjugated by amide bond
formation or‘click-reaction’ approaches.},
cin = {E030 / DD01},
ddc = {610},
cid = {I:(DE-He78)E030-20160331 / I:(DE-He78)DD01-20160331},
pnm = {315 - Bildgebung und Radioonkologie (POF4-315)},
pid = {G:(DE-HGF)POF4-315},
typ = {PUB:(DE-HGF)16},
pubmed = {pmid:36986500},
doi = {10.3390/ph16030401},
url = {https://inrepo02.dkfz.de/record/274564},
}