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

• Published in: Russian chemical bulletin Vol. 72; no. 6; pp. 1349 - 1365
• Main Authors: Kurmaz, S. V., Ivanova, I. I., Fadeeva, N. V., Ignatiev, V. M., Emelyanova, N. S., Lapshina, M. A., Balakina, A. A., Terentiev, A. A.
• Format: Journal Article
• Language: English
• Published: New York Springer US 01-06-2023; Springer Nature B.V
• Subjects: Absorption spectroscopy; Acids; Aqueous solutions; Biocompatibility; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Composition; Copolymers; Fluorescent dyes; Folic acid; Full Articles; Glycol dimethacrylates; Hydrogen atoms; Hydrogen bonds; Infrared spectroscopy; Inorganic Chemistry; Methacrylic acid; NMR; Nuclear magnetic resonance; Organic Chemistry; Oxygen atoms; Polymers; Quantum chemistry; Spectrum analysis; Toxicity; Triethylene glycol dimethacrylate; Vitamin B; triethylene glycol dimethacrylate; amphiphilic copolymers; quantum chemical modeling; fluorescence; vinylpyrrolidone; cellular accumulation; folic acid; methacrylic acid; cytotoxicity
• ISSN: 1066-5285; 1573-9171
• DOI: 10.1007/s11172-023-3910-2

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,
1
H 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.