New Amphiphilic Terpolymers of N-Vinylpyrrolidone with Acrylic Acid and Triethylene Glycol Dimethacrylate as Promising Drug Delivery: Design, Synthesis and Biological Properties In Vitro

Int J Mol Sci. 2024 Aug 1;25(15):8422. doi: 10.3390/ijms25158422.

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 molar composition (98:2:2, 95:5: 2 and 98:2:5) and their monomer composition, absolute molecular masses and hydrodynamic radii in aqueous media were determined. Using the MTT test, these terpolymers were established to be low toxic for non-tumor Vero cells and HeLa tumor cells. Polymer compositions of hydrophobic dye methyl pheophorbide a (MPP) based on studied terpolymers and linear polyvinylpyrrolidone (PVP) were obtained and characterized in water solution. Quantum-chemical modeling of the MPP-copolymer structures was conducted, and the possibility of hydrogen bond formation between terpolymer units and the MPP molecule was shown. 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 found.

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

MeSH terms

  • Acrylates* / chemistry
  • Animals
  • Cell Survival / drug effects
  • Chlorocebus aethiops
  • Drug Delivery Systems
  • HeLa Cells
  • Humans
  • Methacrylates / chemistry
  • Polyethylene Glycols / chemistry
  • Polymers / chemical synthesis
  • Polymers / chemistry
  • Pyrrolidinones / chemistry
  • Vero Cells

Substances

  • acrylic acid
  • Acrylates
  • N-vinyl-2-pyrrolidinone
  • Pyrrolidinones
  • Methacrylates
  • Polyethylene Glycols
  • Polymers