Fluorinated Ferrocene Moieties as a Platform for Redox-Responsive Polymer 19F MRI Theranostics
- Pavel Švec*Pavel Švec*Email: [email protected]Institute of Macromolecular Chemistry, CAS, Heyrovského nám. 2, Prague 6 162 06, Czech RepublicDepartment of Physical and Macromolecular Chemistry, Faculty of Science, Charles University, Hlavova 8, Prague 2 128 43, Czech RepublicMore by Pavel Švec
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- Oleg V. PetrovOleg V. PetrovDepartment of Low Temperature Physics, Faculty of Mathematics and Physics, Charles University, V Holešovičkách 2, Prague 8 180 00, Czech RepublicMore by Oleg V. Petrov
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- Jan LangJan LangDepartment of Low Temperature Physics, Faculty of Mathematics and Physics, Charles University, V Holešovičkách 2, Prague 8 180 00, Czech RepublicMore by Jan Lang
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- Petr ŠtěpničkaPetr ŠtěpničkaDepartment of Inorganic Chemistry, Faculty of Science, Charles University, Hlavova 8, Prague 2 128 43, Czech RepublicMore by Petr Štěpnička
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- Ondřej GroborzOndřej GroborzInstitute of Macromolecular Chemistry, CAS, Heyrovského nám. 2, Prague 6 162 06, Czech RepublicInstitute of Organic Chemistry and Biochemistry, CAS, Flemingovo nám. 2, Prague 6 160 00, Czech RepublicInstitute of Biophysics and Informatics, Charles University, Salmovská 3, Prague 2 120 00, Czech RepublicMore by Ondřej Groborz
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- David DunlopDavid DunlopDepartment of Inorganic Chemistry, Faculty of Science, Charles University, Hlavova 8, Prague 2 128 43, Czech RepublicInstitute of Organic Chemistry and Biochemistry, CAS, Flemingovo nám. 2, Prague 6 160 00, Czech RepublicJ. Heyrovský Institute of Physical Chemistry, CAS, Dolejškova 2155/3, Prague 8 182 23, Czech RepublicMore by David Dunlop
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- Jan BlahutJan BlahutDepartment of NMR Spectroscopy, Faculty of Science, Charles University, Hlavova 8, Prague 2 128 43, Czech RepublicMore by Jan Blahut
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- Kristýna KolouchováKristýna KolouchováInstitute of Macromolecular Chemistry, CAS, Heyrovského nám. 2, Prague 6 162 06, Czech RepublicMore by Kristýna Kolouchová
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- Lenka LoukotováLenka LoukotováInstitute of Macromolecular Chemistry, CAS, Heyrovského nám. 2, Prague 6 162 06, Czech RepublicInstitute of Organic Chemistry and Biochemistry, CAS, Flemingovo nám. 2, Prague 6 160 00, Czech RepublicMore by Lenka Loukotová
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- Ondřej SedláčekOndřej SedláčekDepartment of Physical and Macromolecular Chemistry, Faculty of Science, Charles University, Hlavova 8, Prague 2 128 43, Czech RepublicSupramolecular Chemistry Group, Centre of Macromolecular Chemistry (CMaC), Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281-S4, Ghent B-9000, BelgiumMore by Ondřej Sedláček
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- Tomáš HeizerTomáš HeizerCenter for Advanced Preclinical Imaging, First Faculty of Medicine, Charles University, Salmovská 3, Prague 2 120 00, Czech RepublicMore by Tomáš Heizer
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- Zdeněk TošnerZdeněk TošnerDepartment of NMR Spectroscopy, Faculty of Science, Charles University, Hlavova 8, Prague 2 128 43, Czech RepublicMore by Zdeněk Tošner
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- Miroslav ŠloufMiroslav ŠloufInstitute of Macromolecular Chemistry, CAS, Heyrovského nám. 2, Prague 6 162 06, Czech RepublicMore by Miroslav Šlouf
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- Hynek BenešHynek BenešInstitute of Macromolecular Chemistry, CAS, Heyrovského nám. 2, Prague 6 162 06, Czech RepublicMore by Hynek Beneš
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- Richard HoogenboomRichard HoogenboomSupramolecular Chemistry Group, Centre of Macromolecular Chemistry (CMaC), Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281-S4, Ghent B-9000, BelgiumMore by Richard Hoogenboom
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- Martin Hrubý*Martin Hrubý*Email: [email protected]Institute of Macromolecular Chemistry, CAS, Heyrovského nám. 2, Prague 6 162 06, Czech RepublicMore by Martin Hrubý
Abstract
Fluorine-19 magnetic resonance imaging (19F MRI) stands out as a powerful tool for noninvasive diagnostics. In particular, polymer-based 19F MRI tracers offer tunable physicochemical properties, including solubility and thermoresponsiveness, and enhanced 19F MRI performance. However, these tracers do not detectably respond to redox changes or do so in only one redox state, thereby preventing potential applications to reactive oxygen species (ROS) bioimaging. Herein, we report the first amphiphilic redox-responsive, poly(2-oxazoline)-based polymers bearing fluorinated ferrocene moieties. Their hydrophobicity and redox responsiveness were tailored by changing the monomer ratio and substitution pattern of the fluorinated ferrocene units. Converting the diamagnetic fluorinated ferrocene moieties into paramagnetic ferrocenium markedly changed the chemical shift and relaxation times of the 19F nuclei distinguishable by 19F MRI. In turn, the statistical–diblock copolymers formed nanoparticles that disassemble upon oxidation, with no toxicity to cultured cells. Therefore, these polymers may be used to release lipophilic drugs in ROS-rich malignancies.
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- Kristyna Kolouchova, Zulfiya Cernochova, Ondrej Groborz, Vit Herynek, Filip Koucky, Radek Jaksa, Jiri Benes, Miroslav Slouf, Martin Hruby. Multiresponsive fluorinated polymers as a theranostic platform using 19F MRI. European Polymer Journal 2022, 175 , 111381. https://doi.org/10.1016/j.eurpolymj.2022.111381