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Fluorinated Ferrocene Moieties as a Platform for Redox-Responsive Polymer 19F MRI Theranostics

  • Pavel Švec*
    Pavel Švec
    Institute of Macromolecular Chemistry, CAS, Heyrovského nám. 2, Prague 6 162 06, Czech Republic
    Department of Physical and Macromolecular Chemistry, Faculty of Science, Charles University, Hlavova 8, Prague 2 128 43, Czech Republic
    *Email: [email protected]
    More by Pavel Švec
  • Oleg V. Petrov
    Oleg V. Petrov
    Department of Low Temperature Physics, Faculty of Mathematics and Physics, Charles University, V Holešovičkách 2, Prague 8 180 00, Czech Republic
  • Jan Lang
    Jan Lang
    Department of Low Temperature Physics, Faculty of Mathematics and Physics, Charles University, V Holešovičkách 2, Prague 8 180 00, Czech Republic
    More by Jan Lang
  • Petr Štěpnička
    Petr Štěpnička
    Department of Inorganic Chemistry, Faculty of Science, Charles University, Hlavova 8, Prague 2 128 43, Czech Republic
  • Ondřej Groborz
    Ondřej Groborz
    Institute of Macromolecular Chemistry, CAS, Heyrovského nám. 2, Prague 6 162 06, Czech Republic
    Institute of Organic Chemistry and Biochemistry, CAS, Flemingovo nám. 2, Prague 6 160 00, Czech Republic
    Institute of Biophysics and Informatics, Charles University, Salmovská 3, Prague 2 120 00, Czech Republic
  • David Dunlop
    David Dunlop
    Department of Inorganic Chemistry, Faculty of Science, Charles University, Hlavova 8, Prague 2 128 43, Czech Republic
    Institute of Organic Chemistry and Biochemistry, CAS, Flemingovo nám. 2, Prague 6 160 00, Czech Republic
    J. Heyrovský Institute of Physical Chemistry, CAS, Dolejškova 2155/3, Prague 8 182 23, Czech Republic
    More by David Dunlop
  • Jan Blahut
    Jan Blahut
    Department of NMR Spectroscopy, Faculty of Science, Charles University, Hlavova 8, Prague 2 128 43, Czech Republic
    More by Jan Blahut
  • Kristýna Kolouchová
    Kristýna Kolouchová
    Institute of Macromolecular Chemistry, CAS, Heyrovského nám. 2, Prague 6 162 06, Czech Republic
  • Lenka Loukotová
    Lenka Loukotová
    Institute of Macromolecular Chemistry, CAS, Heyrovského nám. 2, Prague 6 162 06, Czech Republic
    Institute of Organic Chemistry and Biochemistry, CAS, Flemingovo nám. 2, Prague 6 160 00, Czech Republic
  • Ondřej Sedláček
    Ondřej Sedláček
    Department of Physical and Macromolecular Chemistry, Faculty of Science, Charles University, Hlavova 8, Prague 2 128 43, Czech Republic
    Supramolecular Chemistry Group, Centre of Macromolecular Chemistry (CMaC), Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281-S4, Ghent B-9000, Belgium
  • Tomáš Heizer
    Tomáš Heizer
    Center for Advanced Preclinical Imaging, First Faculty of Medicine, Charles University, Salmovská 3, Prague 2 120 00, Czech Republic
  • Zdeněk Tošner
    Zdeněk Tošner
    Department of NMR Spectroscopy, Faculty of Science, Charles University, Hlavova 8, Prague 2 128 43, Czech Republic
  • Miroslav Šlouf
    Miroslav Šlouf
    Institute of Macromolecular Chemistry, CAS, Heyrovského nám. 2, Prague 6 162 06, Czech Republic
  • Hynek Beneš
    Hynek Beneš
    Institute of Macromolecular Chemistry, CAS, Heyrovského nám. 2, Prague 6 162 06, Czech Republic
    More by Hynek Beneš
  • Richard Hoogenboom
    Richard Hoogenboom
    Supramolecular Chemistry Group, Centre of Macromolecular Chemistry (CMaC), Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281-S4, Ghent B-9000, Belgium
  • , and 
  • Martin Hrubý*
    Martin Hrubý
    Institute of Macromolecular Chemistry, CAS, Heyrovského nám. 2, Prague 6 162 06, Czech Republic
    *Email: [email protected]
Cite this: Macromolecules 2022, 55, 2, 658–671
Publication Date (Web):December 29, 2021
https://doi.org/10.1021/acs.macromol.1c01723
Copyright © 2021 American Chemical Society

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    Abstract

    Abstract Image

    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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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.macromol.1c01723.

    • Experimental procedures; copies of 1H, 13C, and 19F NMR spectra; SEC traces; DLS data; cryo-TEM images; cytotoxicity results; DSC data; in silico results; and additional 19F NMR/MRI data (PDF)

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    Cited By

    This article is cited by 3 publications.

    1. Haneul Kwon, Soohyun Kim, Mirim Ham, Yewon Park, Haekyoung Kim, Wonmok Lee, Hyunjung Lee. Enhanced Coloration Time of Electrochromic Device Using Integrated WO3@PEO Electrodes for Wearable Devices. Biosensors 2023, 13 (2) , 194. https://doi.org/10.3390/bios13020194
    2. Yongyi Mo, Chixiang Huang, Changjiang Liu, Ziwei Duan, Juan Liu, Dalin Wu. Recent Research Progress of 19 F Magnetic Resonance Imaging Probes: Principle, Design, and Their Application. Macromolecular Rapid Communications 2023, 242 , 2200744. https://doi.org/10.1002/marc.202200744
    3. 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

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