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Self-Assembly, Drug Encapsulation, and Cellular Uptake of Block and Gradient Copolymers of 2-Methyl-2-oxazine and 2-n-Propyl/butyl-2-oxazoline

  • David Babuka
    David Babuka
    Institute of Macromolecular Chemistry, Czech Academy of Sciences, Heyrovskeho sq. 2, Prague 6 162 06, Czech Republic
    Department of Biophysics, Institute of Physics, Faculty of Mathematics and Physics, Charles University, Ke Karlovu 3, Prague 2 121 16, Czech Republic
    More by David Babuka
  • Kristyna Kolouchova
    Kristyna Kolouchova
    Institute of Macromolecular Chemistry, Czech Academy of Sciences, Heyrovskeho sq. 2, Prague 6 162 06, Czech Republic
    Department of Physical and Macromolecular Chemistry, Faculty of Science, Charles University, Hlavova 8, Prague 2 128 00, Czech Republic
  • Lenka Loukotova
    Lenka Loukotova
    Institute of Macromolecular Chemistry, Czech Academy of Sciences, Heyrovskeho sq. 2, Prague 6 162 06, Czech Republic
  • Ondrej Sedlacek
    Ondrej Sedlacek
    Department of Physical and Macromolecular Chemistry, Faculty of Science, Charles University, Hlavova 8, Prague 2 128 00, Czech Republic
    Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281-S4, 9000 Ghent, Belgium
  • Ondrej Groborz
    Ondrej Groborz
    Institute of Macromolecular Chemistry, Czech Academy of Sciences, Heyrovskeho sq. 2, Prague 6 162 06, Czech Republic
    Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Flemingovo sq. 542, Prague 6 162 06, Czech Republic
    Institute of Biophysics and Informatics, Charles University, First Faculty of Medicine, Salmovská 1, Prague 2 120 00, Czech Republic
  • Aneta Skarkova
    Aneta Skarkova
    Department of Cell Biology, Charles University, Vinicna 7, Prague 12843, Czech Republic
    Biotechnology and Biomedicine Centre of the Academy of Sciences and Charles University (BIOCEV), Prumyslova 595, Vestec u Prahy 25242, Czech Republic
  • Alexander Zhigunov
    Alexander Zhigunov
    Institute of Macromolecular Chemistry, Czech Academy of Sciences, Heyrovskeho sq. 2, Prague 6 162 06, Czech Republic
  • Ewa Pavlova
    Ewa Pavlova
    Institute of Macromolecular Chemistry, Czech Academy of Sciences, Heyrovskeho sq. 2, Prague 6 162 06, Czech Republic
    More by Ewa Pavlova
  • Richard Hoogenboom*
    Richard Hoogenboom
    Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281-S4, 9000 Ghent, Belgium
    *Email: [email protected]
  • Martin Hruby*
    Martin Hruby
    Institute of Macromolecular Chemistry, Czech Academy of Sciences, Heyrovskeho sq. 2, Prague 6 162 06, Czech Republic
    *Email: [email protected]
    More by Martin Hruby
  • , and 
  • Petr Stepanek
    Petr Stepanek
    Institute of Macromolecular Chemistry, Czech Academy of Sciences, Heyrovskeho sq. 2, Prague 6 162 06, Czech Republic
Cite this: Macromolecules 2021, 54, 23, 10667–10681
Publication Date (Web):December 2, 2021
https://doi.org/10.1021/acs.macromol.1c01794
Copyright © 2021 American Chemical Society

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    Abstract

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    Self-assembled amphiphilic polymers have been extensively studied for various biomedical applications, as they show advantageous properties for diagnosis and therapy. In this work, we extensively compared amphiphilic copolymers of the hydrophilic monomer 2-methyl-2-oxazine (MeOzi) and the thermoresponsive or hydrophobic monomers 2-propyl-2-oxazoline (PrOx) or 2-butyl-2-oxazoline (BuOx) in both block and gradient monomer distributions. Such a head-to-head comparison between block and gradient copolymers, which has thus far been mostly missing in the available literature, should provide important insight into the differences and similarities between these two architectures. We investigated the properties of our polymers using a wide array of analytical methods, including dynamic light scattering (DLS), small-angle neutron (SANS) and X-ray scattering (SAXS), one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR) spectroscopy, transmission electron microscopy (TEM), drug loading (DL), cellular uptake, and cytotoxicity studies. Most of the studied polymers formed self-assembled nanoparticles, but their properties varied with the monomer ratio, polymer length, and polymer architecture, and these factors could be used to fine-tune the properties of the polymer to meet the demands of the desired application. Both block and gradient copolymers showed similar critical association concentrations and DL properties for the antituberculosis drug rifampicin. Finally, we confirmed that the nanoparticles could be internalized by macrophages, which indicates great potential for the utilization of these nanoparticles in drug delivery.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.macromol.1c01794.

    • Detailed descriptions of polymer synthesis, SEC summary, 1H NMR spectra, 1H–13C HSQC spectra, 1H–1H COSY spectra, 1H–1H NOESY spectra, DLS measurements, SANS measurements, chart showing the CACs, evaluated CACs, evaluated DL data, and a summary of the cytotoxicity assays (PDF)

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    Cited By

    This article is cited by 7 publications.

    1. Kedafi Belkhir, Orélia Cerlati, Diana Heaugwane, Alice Tosi, Belkacem Tarek Benkhaled, Pierre-Louis Brient, Camille Chatard, Alain Graillot, Sylvain Catrouillet, Stéphanie Balor, Dominique Goudounèche, Bruno Payré, Pascale Laborie, Jia-Hui Lim, Jean-Luc Putaux, Patricia Vicendo, Laure Gibot, Barbara Lonetti, Anne-Françoise Mingotaud, Vincent Lapinte. Synthesis and Self-Assembly of UV-Cross-Linkable Amphiphilic Polyoxazoline Block Copolymers: Importance of Multitechnique Characterization. Langmuir 2022, 38 (51) , 16144-16155. https://doi.org/10.1021/acs.langmuir.2c02896
    2. Jungyeon Kim, Beatrice Cattoz, Alice H. M. Leung, James D. Parish, C. Remzi Becer. Enabling Reversible Addition-Fragmentation Chain-Transfer Polymerization for Brush Copolymers with a Poly(2-oxazoline) Backbone. Macromolecules 2022, 55 (11) , 4411-4419. https://doi.org/10.1021/acs.macromol.2c00497
    3. Liuxin Yang, Faming Wang, Pengfei Ren, Tianzhu Zhang, Qianli Zhang. Poly(2-oxazoline)s: synthesis and biomedical applications. Macromolecular Research 2023, 4 https://doi.org/10.1007/s13233-023-00116-x
    4. Shubhashis Datta, Veronika Huntošová, Annamária Jutková, Róbert Seliga, Juraj Kronek, Adriána Tomkova, Lenka Lenkavská, Mariana Máčajová, Boris Bilčík, Barbora Kundeková, Ivan Čavarga, Ewa Pavlova, Miroslav Šlouf, Pavol Miškovský, Daniel Jancura. Influence of Hydrophobic Side-Chain Length in Amphiphilic Gradient Copoly(2-oxazoline)s on the Therapeutics Loading, Stability, Cellular Uptake and Pharmacokinetics of Nano-Formulation with Curcumin. Pharmaceutics 2022, 14 (12) , 2576. https://doi.org/10.3390/pharmaceutics14122576
    5. Richard Hoogenboom. The future of poly(2-oxazoline)s. European Polymer Journal 2022, 179 , 111521. https://doi.org/10.1016/j.eurpolymj.2022.111521
    6. Jiwon Jeong, Jungju Ryu, Younhee Jeong, Zuzana Kroneková, Juraj Kronek, Daewon Sohn. Aggregation behaviors of gradient and diblock copoly(2-oxazoline) monolayers at the air-water interface. Polymer 2022, 259 , 125352. https://doi.org/10.1016/j.polymer.2022.125352
    7. 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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