Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

New Amphiphilic Terpolymers of N-Vinylpyrrolidone with Acrylic Acid and Triethylene Glycol Dimethacrylate: Design, Synthesis and Biomedical Applications

Version 1 : Received: 4 June 2024 / Approved: 5 June 2024 / Online: 5 June 2024 (15:22:37 CEST)

How to cite: Kurmaz, S. V.; Komendant, R. I.; Perepelitsina, E. O.; Kurmaz, V. A.; Emelyanova, N. S.; Filatova, N. V.; Amozova, V. I.; Balakina, A. A.; Terentyev, A. A. New Amphiphilic Terpolymers of N-Vinylpyrrolidone with Acrylic Acid and Triethylene Glycol Dimethacrylate: Design, Synthesis and Biomedical Applications. Preprints 2024, 2024060303. https://doi.org/10.20944/preprints202406.0303.v1 Kurmaz, S. V.; Komendant, R. I.; Perepelitsina, E. O.; Kurmaz, V. A.; Emelyanova, N. S.; Filatova, N. V.; Amozova, V. I.; Balakina, A. A.; Terentyev, A. A. New Amphiphilic Terpolymers of N-Vinylpyrrolidone with Acrylic Acid and Triethylene Glycol Dimethacrylate: Design, Synthesis and Biomedical Applications. Preprints 2024, 2024060303. https://doi.org/10.20944/preprints202406.0303.v1

Abstract

The terpolymers of N-vinylpyrrolidone (VP) with acrylic acid and triethylene glycol methacrylate were synthesized with more than 90% yield by radical copolymerization in ethanol from monomeric mixtures of different composition (98 : 2 : 2, 95 : 5: 2 and 98 : 2: 5). Their physical and chemical characteristics such as monomer composition, absolute molecular masses and hy-drodynamic radii in aqueous media at different temperature were determined. The temperature effect on the behavior of terpolymers in water and aqueous saline buffer solution with pH 7.4 has been studied and the ability of a copolymer enriched with dimethacrylates units was discovered to respond to a temperature change in these media. On the basis of terpolymers and linear polyvi-nylpyrrolidone (PVP), polymer compositions of hydrophobic dye methyl pheophorbide a, MPP, that is fluorescent in the red region of the spectrum, were obtained; the sizes of the polymer nanostructures of MPP in water were determined. The structures based on terpolymers were demonstrated to be more stable than MPP-PVP ones. It was carried out the quantum-chemical modelling of the possible structures of MPP-copolymer that formed as a result of intermolecular interaction between MPP and terpolymer’s chains; the possibility of the formation of hydrogen bonds between the donors of the electrons of terpolymer units and the proton donors of the MPP molecule was shown. Using the MTT test, it was established that copolymers of various compositions are low toxic for non-tumor Vero cells and HeLa tumor cells. It was shown that the cytotoxicity of polymer particles loaded with MPP for FetMSC and HeLa cells increased. Using fluorescence microscopy, the accumulation and distribution of polymer particles in non-tumor (FetMSC) and tumor (HeLa) cells was studied and an increase in the accumulation of MPP with both types of particles was shown.

Keywords

N-vinylpyrrolidone; acrylic acid; triethylene glycol dimethacrylate; radical terpolymerization; amphiphilic terpolymers; functional compound; methylphemophide a; biological activity; cell accumulation; medicinal chemistry

Subject

Chemistry and Materials Science, Materials Science and Technology

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