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Fluorinated ferrocene moieties as a platform for redox-responsive polymer F-19 MRI theranostics

Pavel Svec, V Petrov, Oleg, Jan Lang, Petr Stepnicka, Ondrej Groborz, David Dunlop, Jan Blahut, Kristyna Kolouchova, Lenka Loukotova, Ondrej Sedlacek (UGent) , et al.
(2022) MACROMOLECULES. 55(2). p.658-671
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Abstract
Fluorine-19 magnetic resonance imaging (F-19 MRI) stands out as a powerful tool for noninvasive diagnostics. In particular, polymer-based F-19 MRI tracers ofler tunable physicochemical properties, including solubility and thermoresponsive-ness, and enhanced F-19 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 F-19 nuclei distinguishable by F-19 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.
Keywords
MAGNETIC-RESONANCE, MOLECULAR-OXYGEN, ROS, DECOMPOSITION, REDUCTION, COMPLEX, CANCER, AGENTS, CELLS, POLY(2-OXAZOLINE)S

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MLA
Svec, Pavel, et al. “Fluorinated Ferrocene Moieties as a Platform for Redox-Responsive Polymer F-19 MRI Theranostics.” MACROMOLECULES, vol. 55, no. 2, 2022, pp. 658–71, doi:10.1021/acs.macromol.1c01723.
APA
Svec, P., Petrov, Oleg, V., Lang, J., Stepnicka, P., Groborz, O., Dunlop, D., … Hruby, M. (2022). Fluorinated ferrocene moieties as a platform for redox-responsive polymer F-19 MRI theranostics. MACROMOLECULES, 55(2), 658–671. https://doi.org/10.1021/acs.macromol.1c01723
Chicago author-date
Svec, Pavel, V Petrov, Oleg, Jan Lang, Petr Stepnicka, Ondrej Groborz, David Dunlop, Jan Blahut, et al. 2022. “Fluorinated Ferrocene Moieties as a Platform for Redox-Responsive Polymer F-19 MRI Theranostics.” MACROMOLECULES 55 (2): 658–71. https://doi.org/10.1021/acs.macromol.1c01723.
Chicago author-date (all authors)
Svec, Pavel, V Petrov, Oleg, Jan Lang, Petr Stepnicka, Ondrej Groborz, David Dunlop, Jan Blahut, Kristyna Kolouchova, Lenka Loukotova, Ondrej Sedlacek, Tomas Heizer, Zdenek Tosner, Miroslav Slouf, Hynek Benes, Richard Hoogenboom, and Martin Hruby. 2022. “Fluorinated Ferrocene Moieties as a Platform for Redox-Responsive Polymer F-19 MRI Theranostics.” MACROMOLECULES 55 (2): 658–671. doi:10.1021/acs.macromol.1c01723.
Vancouver
1.
Svec P, Petrov, Oleg V, Lang J, Stepnicka P, Groborz O, Dunlop D, et al. Fluorinated ferrocene moieties as a platform for redox-responsive polymer F-19 MRI theranostics. MACROMOLECULES. 2022;55(2):658–71.
IEEE
[1]
P. Svec et al., “Fluorinated ferrocene moieties as a platform for redox-responsive polymer F-19 MRI theranostics,” MACROMOLECULES, vol. 55, no. 2, pp. 658–671, 2022.
@article{8745946,
  abstract     = {{Fluorine-19 magnetic resonance imaging (F-19 MRI) stands out as a powerful tool for noninvasive diagnostics. In particular, polymer-based F-19 MRI tracers ofler tunable physicochemical properties, including solubility and thermoresponsive-ness, and enhanced F-19 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 F-19 nuclei distinguishable by F-19 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.}},
  author       = {{Svec, Pavel and Petrov, Oleg, V and Lang, Jan and Stepnicka, Petr and Groborz, Ondrej and Dunlop, David and Blahut, Jan and Kolouchova, Kristyna and Loukotova, Lenka and Sedlacek, Ondrej and Heizer, Tomas and Tosner, Zdenek and Slouf, Miroslav and Benes, Hynek and Hoogenboom, Richard and Hruby, Martin}},
  issn         = {{0024-9297}},
  journal      = {{MACROMOLECULES}},
  keywords     = {{MAGNETIC-RESONANCE,MOLECULAR-OXYGEN,ROS,DECOMPOSITION,REDUCTION,COMPLEX,CANCER,AGENTS,CELLS,POLY(2-OXAZOLINE)S}},
  language     = {{eng}},
  number       = {{2}},
  pages        = {{658--671}},
  title        = {{Fluorinated ferrocene moieties as a platform for redox-responsive polymer F-19 MRI theranostics}},
  url          = {{http://doi.org/10.1021/acs.macromol.1c01723}},
  volume       = {{55}},
  year         = {{2022}},
}
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