Quaternary Ammonium Chitosans: The Importance of the Positive Fixed Charge of the Drug Delivery Systems

Int J Mol Sci. 2020 Sep 10;21(18):6617. doi: 10.3390/ijms21186617.

Abstract

As a natural polysaccharide, chitosan has good biocompatibility, biodegradability and biosecurity. The hydroxyl and amino groups present in its structure make it an extremely versatile and chemically modifiable material. In recent years, various synthetic strategies have been used to modify chitosan, mainly to solve the problem of its insolubility in neutral physiological fluids. Thus, derivatives with negative or positive fixed charge were synthesized and used to prepare innovative drug delivery systems. Positively charged conjugates showed improved properties compared to unmodified chitosan. In this review the main quaternary ammonium derivatives of chitosan will be considered, their preparation and their applications will be described to evaluate the impact of the positive fixed charge on the improvement of the properties of the drug delivery systems based on these polymers. Furthermore, the performances of the proposed systems resulting from in vitro and ex vivo experiments will be taken into consideration, with particular attention to cytotoxicity of systems, and their ability to promote drug absorption.

Keywords: N-2-hydroxypropyl trimethyl ammonium chitosan; diethylmethyl chitosan; dimethylethyl chitosan; ex vivo studies; in vitro studies; quaternary carboxymethyl chitosan derivatives; trimethyl chitosan.

Publication types

  • Review

MeSH terms

  • Chitosan / analogs & derivatives*
  • Drug Delivery Systems*
  • Quaternary Ammonium Compounds / chemistry*

Substances

  • Quaternary Ammonium Compounds
  • Chitosan