Synthesis and in vitro antimicrobial and antioxidant activities of quaternary ammonium chitosan modified with nisin

J Biomater Sci Polym Ed. 2017 Dec;28(17):2034-2052. doi: 10.1080/09205063.2017.1368615. Epub 2017 Aug 30.

Abstract

Nisin had been grafted onto quaternary ammonium chitosan (QCS) through an enzyme-catalyzed reaction to enhance its limited antimicrobial activity. QCS was synthesized by incorporating N-(3-chloro-2-hydroxypropyl) trimethyl ammonium chloride (CHPTAC) onto chitosan's primary amine group. The modification had been confirmed by FT-IR and 1H NMR spectroscopy. Degree of substitution (DS) of QCS-nisin could be controlled by adjusting the reaction conditions. The synthesized compounds were screened in vitro to evaluate their antimicrobial and antioxidant activities. The results suggested that QCS-nisin significantly suppressed the growth of both gram-positive bacteria and gram-negative bacteria; The antioxidant effects on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical, hydroxyl radical and hydrogen peroxide (H2O2) proved to be enhanced with increasing DS and concentration. In addition, QCS-nisin showed excellent moisture absorption and retention properties; MTT assay exhibited that QCS-nisin revealed low cytotoxicity effects on cultured NIH-3T3 fibroblasts. These results suggest that QCS-nisin would appear to be a promising candidate for wound dressing application.

Keywords: Quaternary ammonium chitosan; antimicrobial; antioxidant; nisin.

MeSH terms

  • 3T3 Cells
  • Animals
  • Anti-Infective Agents* / chemical synthesis
  • Anti-Infective Agents* / chemistry
  • Anti-Infective Agents* / pharmacology
  • Antioxidants* / chemical synthesis
  • Antioxidants* / chemistry
  • Antioxidants* / pharmacology
  • Cell Survival / drug effects
  • Chitosan* / analogs & derivatives
  • Chitosan* / chemical synthesis
  • Chitosan* / pharmacology
  • Escherichia coli / drug effects
  • Humans
  • Mice
  • Nisin
  • Proton Magnetic Resonance Spectroscopy
  • Quaternary Ammonium Compounds* / chemical synthesis
  • Quaternary Ammonium Compounds* / pharmacology
  • Spectroscopy, Fourier Transform Infrared
  • Staphylococcus aureus / drug effects

Substances

  • Anti-Infective Agents
  • Antioxidants
  • Quaternary Ammonium Compounds
  • Nisin
  • Chitosan