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t-Bu2SiF-Derivatized D2-Receptor Ligands: The First SiFA-Containing Small Molecule Radiotracers for Target-Specific PET-Imaging

Department of Inorganic Chemistry II, Faculty of Chemistry, TU Dortmund, Otto-Hahn-Str. 6, 44221 Dortmund, Germany
Department of Nuclear Medicine, Ludwig-Maximilians-University, Marchioninistr. 15, 81377 Munich, Germany
Department of Pharmacy, Center for Drug Research, Ludwig-Maximilians-University, Butenandtstr. 7, 81377 Munich, Germany
GE Global Research, 85748 Garching, Germany
McConnell Brain Imaging Centre, Montreal Neurological Institute, McGill University, 3801 University St., Montreal H3A 2B4, QC, Canada
Authors to whom correspondence should be addressed.
Molecules 2011, 16(9), 7458-7479;
Received: 28 July 2011 / Revised: 19 August 2011 / Accepted: 31 August 2011 / Published: 2 September 2011
(This article belongs to the Special Issue Fluorine Chemistry 2016)
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The synthesis, radiolabeling and in vitro evaluation of new silicon-fluoride acceptor (SiFA) derivatized D2-receptor ligands is reported. The SiFA-technology simplifies the introduction of fluorine-18 into target specific biomolecules for Positron-Emission-Tomography (PET). However, one of the remaining challenges, especially for small molecules such as receptor-ligands, is the bulkiness of the SiFA-moiety. We therefore synthesized four Fallypride SiFA-conjugates derivatized either directly at the benzoic acid ring system (SiFA-DMFP, SiFA-FP, SiFA-DDMFP) or at the butyl-side chain (SiFA-M-FP) and tested their receptor affinities. We found D2-receptor affinities for all compounds in the nanomolar range (Ki(SiFA-DMFP) = 13.6 nM, Ki(SiFA-FP) = 33.0 nM, Ki(SiFA-DDMFP) = 62.7 nM and Ki(SiFA-M-FP) = 4.21 nM). The radiofluorination showed highest yields when 10 nmol of the precursors were reacted with [18F]fluoride/TBAHCO3 in acetonitrile. After a reversed phased cartridge purification the desired products could be isolated as an injectable solution after only 10 min synthesis time with radiochemical yields (RCY) of more than 40% in the case of SiFA-DMFP resulting in specific activities >41 GBq/µmol (>1,100 Ci/mmol). Furthermore, the radiolabeled products were shown to be stable in the injectable solutions, as well as in human plasma, for at least 90 min. View Full-Text
Keywords: fluorine; isotopic labeling; positron emission tomography; radiopharmaceuticals; silicon fluorine; isotopic labeling; positron emission tomography; radiopharmaceuticals; silicon

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Iovkova-Berends, L.; Wängler, C.; Zöller, T.; Höfner, G.; Wanner, K.T.; Rensch, C.; Bartenstein, P.; Kostikov, A.; Schirrmacher, R.; Jurkschat, K.; Wängler, B. t-Bu2SiF-Derivatized D2-Receptor Ligands: The First SiFA-Containing Small Molecule Radiotracers for Target-Specific PET-Imaging. Molecules 2011, 16, 7458-7479.

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