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Fluorine-containing block and gradient copoly(2-oxazoline)s based on 2-(3,3,3-Trifluoropropyl)-2-oxazoline : a quest for the optimal self-assembled structure for F-19 imaging

I Kaberov, Leonid, Zhansaya Kaberova, Anastasiia Murmiliuk, Jiri Trousil, Ondrej Sedlacek, Rafal Konefal, Alexander Zhigunov, Ewa Pavlova, Martin Vit, Daniel Jirak, et al.
(2021) BIOMACROMOLECULES. 22(7). p.2963-2975
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Abstract
The use of fluorinated contrast agents in magnetic resonance imaging (MRI) facilitates improved image quality due to the negligible amount of endogenous fluorine atoms in the body. In this work, we present a comprehensive study of the influence of the amphiphilic polymer structure and composition on its applicability as contrast agents in F-19 MRI. Three series of novel fluorine-containing poly(2-oxazoline) copolymers and terpolymers, hydrophilic-fluorophilic, hydrophilic-lipophilic-fluorophilic, and hydrophilic-thermoresponsive-fluorophilic, with block and gradient distributions of the fluorinated units, were synthesized. It was discovered that the CF3 in the 2-(3,3,3-trifluoropropyl)-2-oxazoline (CF3EtOx) group activated the cationic chain end, leading to faster copolymerization kinetics, whereby spontaneous monomer gradients were formed with accelerated incorporation of 2-methyl-2-oxazoline or 2-n-propyl-2-oxazoline with a gradual change to the less-nucleophilic CF3EtOx monomer. The obtained amphiphilic copolymers and terpolymers form spherical or wormlike micelles in water, which was confirmed using transmission electron microscopy (TEM), while small-angle X-ray scattering (SAXS) revealed the core-shell or core-double-shell morphologies of these nanoparticles. The core and shell sizes obey the scaling laws for starlike micelles predicted by the scaling theory. Biocompatibility studies confirm that all copolymers obtained are noncytotoxic and, at the same time, exhibit high sensitivity during in vitro F-19 MRI studies. The gradient copolymers provide the best F-19 MRI signal-to-noise ratio in comparison with the analogue block copolymer structures, making them most promising as F-19 MRI contrast agents.
Keywords
MRI CONTRAST AGENTS, RING-OPENING POLYMERIZATION, IN-VITRO CYTOTOXICITY, COPOLYMERS, MICELLES, NANOPARTICLES, CHEMISTRY, POLY(2-OXAZOLINE)S, MACROMOLECULES, TRACKING

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Citation

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MLA
Kaberov, Leonid, I., et al. “Fluorine-Containing Block and Gradient Copoly(2-Oxazoline)s Based on 2-(3,3,3-Trifluoropropyl)-2-Oxazoline : A Quest for the Optimal Self-Assembled Structure for F-19 Imaging.” BIOMACROMOLECULES, vol. 22, no. 7, 2021, pp. 2963–75, doi:10.1021/acs.biomac.1c00367.
APA
Kaberov, Leonid, I., Kaberova, Z., Murmiliuk, A., Trousil, J., Sedlacek, O., Konefal, R., … Filippov, S. K. (2021). Fluorine-containing block and gradient copoly(2-oxazoline)s based on 2-(3,3,3-Trifluoropropyl)-2-oxazoline : a quest for the optimal self-assembled structure for F-19 imaging. BIOMACROMOLECULES, 22(7), 2963–2975. https://doi.org/10.1021/acs.biomac.1c00367
Chicago author-date
Kaberov, Leonid, I, Zhansaya Kaberova, Anastasiia Murmiliuk, Jiri Trousil, Ondrej Sedlacek, Rafal Konefal, Alexander Zhigunov, et al. 2021. “Fluorine-Containing Block and Gradient Copoly(2-Oxazoline)s Based on 2-(3,3,3-Trifluoropropyl)-2-Oxazoline : A Quest for the Optimal Self-Assembled Structure for F-19 Imaging.” BIOMACROMOLECULES 22 (7): 2963–75. https://doi.org/10.1021/acs.biomac.1c00367.
Chicago author-date (all authors)
Kaberov, Leonid, I, Zhansaya Kaberova, Anastasiia Murmiliuk, Jiri Trousil, Ondrej Sedlacek, Rafal Konefal, Alexander Zhigunov, Ewa Pavlova, Martin Vit, Daniel Jirak, Richard Hoogenboom, and Sergey K. Filippov. 2021. “Fluorine-Containing Block and Gradient Copoly(2-Oxazoline)s Based on 2-(3,3,3-Trifluoropropyl)-2-Oxazoline : A Quest for the Optimal Self-Assembled Structure for F-19 Imaging.” BIOMACROMOLECULES 22 (7): 2963–2975. doi:10.1021/acs.biomac.1c00367.
Vancouver
1.
Kaberov, Leonid I, Kaberova Z, Murmiliuk A, Trousil J, Sedlacek O, Konefal R, et al. Fluorine-containing block and gradient copoly(2-oxazoline)s based on 2-(3,3,3-Trifluoropropyl)-2-oxazoline : a quest for the optimal self-assembled structure for F-19 imaging. BIOMACROMOLECULES. 2021;22(7):2963–75.
IEEE
[1]
I. Kaberov, Leonid et al., “Fluorine-containing block and gradient copoly(2-oxazoline)s based on 2-(3,3,3-Trifluoropropyl)-2-oxazoline : a quest for the optimal self-assembled structure for F-19 imaging,” BIOMACROMOLECULES, vol. 22, no. 7, pp. 2963–2975, 2021.
@article{8724364,
  abstract     = {{The use of fluorinated contrast agents in magnetic resonance imaging (MRI) facilitates improved image quality due to the negligible amount of endogenous fluorine atoms in the body. In this work, we present a comprehensive study of the influence of the amphiphilic polymer structure and composition on its applicability as contrast agents in F-19 MRI. Three series of novel fluorine-containing poly(2-oxazoline) copolymers and terpolymers, hydrophilic-fluorophilic, hydrophilic-lipophilic-fluorophilic, and hydrophilic-thermoresponsive-fluorophilic, with block and gradient distributions of the fluorinated units, were synthesized. It was discovered that the CF3 in the 2-(3,3,3-trifluoropropyl)-2-oxazoline (CF3EtOx) group activated the cationic chain end, leading to faster copolymerization kinetics, whereby spontaneous monomer gradients were formed with accelerated incorporation of 2-methyl-2-oxazoline or 2-n-propyl-2-oxazoline with a gradual change to the less-nucleophilic CF3EtOx monomer. The obtained amphiphilic copolymers and terpolymers form spherical or wormlike micelles in water, which was confirmed using transmission electron microscopy (TEM), while small-angle X-ray scattering (SAXS) revealed the core-shell or core-double-shell morphologies of these nanoparticles. The core and shell sizes obey the scaling laws for starlike micelles predicted by the scaling theory. Biocompatibility studies confirm that all copolymers obtained are noncytotoxic and, at the same time, exhibit high sensitivity during in vitro F-19 MRI studies. The gradient copolymers provide the best F-19 MRI signal-to-noise ratio in comparison with the analogue block copolymer structures, making them most promising as F-19 MRI contrast agents.}},
  author       = {{Kaberov, Leonid, I and Kaberova, Zhansaya and Murmiliuk, Anastasiia and Trousil, Jiri and Sedlacek, Ondrej and Konefal, Rafal and Zhigunov, Alexander and Pavlova, Ewa and Vit, Martin and Jirak, Daniel and Hoogenboom, Richard and Filippov, Sergey K.}},
  issn         = {{1525-7797}},
  journal      = {{BIOMACROMOLECULES}},
  keywords     = {{MRI CONTRAST AGENTS,RING-OPENING POLYMERIZATION,IN-VITRO CYTOTOXICITY,COPOLYMERS,MICELLES,NANOPARTICLES,CHEMISTRY,POLY(2-OXAZOLINE)S,MACROMOLECULES,TRACKING}},
  language     = {{eng}},
  number       = {{7}},
  pages        = {{2963--2975}},
  title        = {{Fluorine-containing block and gradient copoly(2-oxazoline)s based on 2-(3,3,3-Trifluoropropyl)-2-oxazoline : a quest for the optimal self-assembled structure for F-19 imaging}},
  url          = {{http://doi.org/10.1021/acs.biomac.1c00367}},
  volume       = {{22}},
  year         = {{2021}},
}
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