Synthesis and characterization of chitosan quaternary ammonium salt and its application as drug carrier for ribavirin

Drug Deliv. 2014 Nov;21(7):548-52. doi: 10.3109/10717544.2013.853708. Epub 2013 Nov 12.

Abstract

N-(2-hydroxyl) propyl-3-trimethyl ammonium chitosan chloride (HTCC) is hydro-soluble chitosan (CS) derivative, which can be obtained by the reaction between epoxypropyl trimethyl ammonium chloride (ETA) and CS. The preparation parameters for the synthesis of HTCC were optimized by orthogonal experimental design. ETA was successfully grafted into the free amino group of CS. Grafting of ETA with CS had great effect on the crystal structure of HTCC, which was confirmed by the XRD results. HTCC displayed higher capability to form nanoparticles by crosslinking with negatively charged sodium tripolyphosphate (TPP). Ribavrin- (RIV-) loaded HTCC nanoparticles were positively charged and were spherical in shape with average particle size of 200 nm. More efficient drug encapsulation efficiency and loading capacity were obtained for HTCC in comparison with CS, however, HTCC nanoparticles displayed faster release rate due to its hydro-soluble properties. The results suggest that HTCC is a promising CS derivative for the encapsulation of hydrophilic drugs in obtaining sustained release of drugs.

Keywords: Chemical modification; chitosan; drug delivery system; nanoparticles; ribavirin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiviral Agents / administration & dosage
  • Antiviral Agents / chemical synthesis
  • Chemistry, Pharmaceutical / methods*
  • Chitosan / administration & dosage
  • Chitosan / chemical synthesis*
  • Drug Carriers / administration & dosage
  • Drug Carriers / chemical synthesis*
  • Nanoparticles / administration & dosage
  • Nanoparticles / chemistry*
  • Ribavirin / administration & dosage
  • Ribavirin / chemical synthesis*
  • X-Ray Diffraction

Substances

  • Antiviral Agents
  • Drug Carriers
  • N-trimethyl chitosan chloride
  • Ribavirin
  • Chitosan