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Nanoscale systems folic acid—amphiphilic copolymer of N-vinylpyrrolidone with methacrylic acid, branched with triethylene glycol dimethacrylate

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Abstract

Polymer compositions of folic acid based on an amphiphilic copolymer of N-vinylpyrrolidone with methacrylic acid, branched with triethylene glycol dimethacrylate, were developed and characterized by DLS, 1H NMR, IR spectroscopy, DSC, and TGA in solutions and in the solid state. Electron absorption spectroscopy was used to determine the effective binding constant of folic acid and the copolymer in isopropanol and in aqueous media. The behavior of nanoscale systems in water depending on the medium temperature and pH was studied, and their hydrodynamic radii were determined. Quantum chemical modeling of the structure of the intermolecular complexes was carried out, and it was shown that the hydrogen bonds formed by oxygen atoms of carboxy groups of either folic acid or methacrylic acid units and hydrogen atoms are weak. The cytotoxicity of polymer compositions with different contents of folic acid (0.5–4 wt.%) was studied on normal (FetMSC, Vero) and tumor cell cultures, namely, HeLa (human cervical adenocarcinoma, clone M-HeLa) and HepG2 (human liver carcinoma), and their high biocompatibility was demonstrated. Fluorescence microscopy was used to study the accumulation dynamics of polymer particles loaded with folic acid and a fluorescent dye, namely, zinc tetraphenylporphyrinate, in Vero and HeLa cells. Inferences were made about the prospects of the obtained compositions as targeted delivery systems.

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Author information

Authors and Affiliations

  1. Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences, 1 prosp. Akad. Semenova, 142432, Chernogolovka, Moscow Region, Russian Federation

    S. V. Kurmaz, I. I. Ivanova, N. V. Fadeeva, V. M. Ignatiev, N. S. Emelyanova, A. A. Balakina & A. A. Terentiev

  2. Faculty of Fundamental Physical and Chemical Engineering, Lomonosov Moscow State University, Build. 51, 1 Leninskie Gory, 119991, Moscow, Russian Federation

    V. M. Ignatiev & A. A. Terentiev

  3. Institute of Physiologically Active Compounds of the Federal State Budgetary Institution of Science of the Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences, 1 Severnyi proezd, 142432, Chernogolovka, Moscow Region, Russian Federation

    M. A. Lapshina

  4. Research and Education Center of the Moscow State Regional University, 24 ul. Very Voloshinoy, 141014, Mytishchi, Moscow Region, Russian Federation

    A. A. Terentiev

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  1. S. V. Kurmaz
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  2. I. I. Ivanova
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  3. N. V. Fadeeva
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  4. V. M. Ignatiev
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  5. N. S. Emelyanova
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  6. M. A. Lapshina
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  7. A. A. Balakina
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  8. A. A. Terentiev
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Corresponding author

Correspondence to S. V. Kurmaz.

Additional information

This work was carried out according to the Topics of the Russian state assignment (State registration AAAA-A19-119071890015-6 and AAAA-A19-119041090087-4). The work was performed using the equipment of the Analytical Center for Collective Use of the Federal Research Center of Problems of Chemical Physics of the Russian Academy of Sciences.

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 6, pp. 1349–1365, June, 2023.

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Kurmaz, S.V., Ivanova, I.I., Fadeeva, N.V. et al. Nanoscale systems folic acid—amphiphilic copolymer of N-vinylpyrrolidone with methacrylic acid, branched with triethylene glycol dimethacrylate. Russ Chem Bull 72, 1349–1365 (2023). https://doi.org/10.1007/s11172-023-3910-2

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