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| Home > Publications database > Efforts toward PET-Activatable Red-Shifted Silicon Rhodamines and Silicon Pyronine Dyes |
| Home > Publications database > Efforts toward PET-Activatable Red-Shifted Silicon Rhodamines and Silicon Pyronine Dyes |
| Journal Article | DKFZ-2023-00641 |
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2023
MDPI
Basel
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Please use a persistent id in citations: doi:10.3390/ph16030401
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.
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