Dextran-based nanoparticles with 5-FU-conjugated polymethacrylate segments for drug delivery: Synthesis of amphiphilic graft copolymers by mechanochemical solid-state polymerization and characterization

Int J Biol Macromol. 2024 Aug;274(Pt 2):132950. doi: 10.1016/j.ijbiomac.2024.132950. Epub 2024 Jun 5.

Abstract

Dextran (Dx) is a biodegradable and biocompatible polysaccharide, thus promising as a drug delivery carrier for tumor therapy. Herein, we applied mechanical energy to a high molecular weight Dx to control its molecular weight and simultaneously generate mechanoradicals. The solid-state polymerization of methacrylate- or methacrylamide derivatives initiated with Dx mechanoradicals showed polymer conversion of >95%, yielding Dx-based graft copolymers with molecular weights of approximately 30,000 g mol-1. The Dx-based graft copolymers with hydrophobic segments formed nanoparticles with a particle size of 25-35 nm in an aqueous solution. The anti-pancreatic tumor drug 5-fluorouracil (5-FU) was covalently conjugated onto the hydrophobic segments of the amphiphilic Dx, and the nanoparticles were also prepared. The drug release profile from 5-FU-conjugated nanoparticles corresponded well to the Korsmeyer-Peppas model applied to drug release from matrix substrates, and was also immensely predicted by the Logistic and Gompertz curves. The 5-FU-conjugated nanoparticles showed cytotoxicity against the pancreatic adenocarcinoma cell lines (BxPC-3) that were not significantly inferior to the 5-FU positive group. Furthermore, the fluorescein-labeled nanoparticles internalized into BxPC-3 within 6 h and actively migrated into the cytosol. These results suggest that Dx-based graft copolymers with hydrophobic segments might be used to enhance therapeutic activity.

Keywords: Cancer; Dextran; Drug delivery; Drug release; Graft copolymer; Solid-state polymerization.

MeSH terms

  • Cell Line, Tumor
  • Dextrans* / chemistry
  • Drug Carriers* / chemical synthesis
  • Drug Carriers* / chemistry
  • Drug Delivery Systems
  • Drug Liberation
  • Fluorouracil* / chemistry
  • Fluorouracil* / pharmacology
  • Humans
  • Hydrophobic and Hydrophilic Interactions
  • Nanoparticles* / chemistry
  • Particle Size
  • Polymerization*
  • Polymethacrylic Acids / chemical synthesis
  • Polymethacrylic Acids / chemistry

Substances

  • Fluorouracil
  • Dextrans
  • Drug Carriers
  • Polymethacrylic Acids
  • polymethacrylic acid