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Comparative Study
. 2022 Jan 19;20(2):86.
doi: 10.3390/md20020086.

Antimicrobial and Antioxidant Activities of N-2-Hydroxypropyltrimethyl Ammonium Chitosan Derivatives Bearing Amino Acid Schiff Bases

Jingmin Cui  1   2   3 , Xia Ji  4 , Yingqi Mi  1   2   3 , Qin Miao  1   2   3 , Fang Dong  1   3 , Wenqiang Tan  1   3 , Zhanyong Guo  1   2   3
Affiliations
Comparative Study

Antimicrobial and Antioxidant Activities of N-2-Hydroxypropyltrimethyl Ammonium Chitosan Derivatives Bearing Amino Acid Schiff Bases

Jingmin Cui et al. Mar Drugs. .

Abstract

N-2-hydroxypropyltrimethyl ammonium chloride chitosan (HACC), a cationic quaternary ammonium salt polymer exhibiting good solubility in water, is widely used because of its low toxicity and good biocompatibility. Herein, through ion exchange reaction, we prepared N-2-hydroxypropyltrimethyl ammonium chitosan derivatives bearing amino acid Schiff bases with good biological activities. The accuracy of the structures was verified by FT-IR and 1H NMR. The antibacterial activity, antifungal activity, and scavenging ability of DPPH radical and superoxide radical of HACC derivatives were significantly improved compared with that of HACC. In particular, HACGM (HACC-potassium 2-((2-hydroxy-3-methoxybenzylidene)amino)acetate) and HACGB (HACC-potassium 2-((5-bromo-2-hydroxybenzylidene)amino)acetate) showed good inhibitory effect on bacteria and fungi, including Staphylococcus aureus, Escherichia coli, Botrytis cinerea, and Fusarium oxysporum f. sp. cubense. The inhibition rate of HACGB on Staphylococcus aureus and Escherichia coli could reach 100% at the concentration of 0.1 mg/mL, and the inhibition rate of HACGM and HACGB on Botrytis cinerea and Fusarium oxysporum f. sp. cubense could also reach 100% at the concentration of 0.5 mg/mL. Improving antimicrobial and antioxidant activities of HACC could provide ideas and experiences for the development and utilization of chitosan derivatives.

Keywords: N-2-hydroxypropyltrimethyl ammonium chloride chitosan; amino acid Schiff bases; antimicrobial activity; antioxidant activity.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Synthesis pathway of chitosan derivatives of HACC and HACC derivatives.
Figure 1
Figure 1
Fourier Transform Infrared (FT-IR) spectra of HACC and HACC derivatives.
Figure 2
Figure 2
1H NMR spectra of HACC and HACC derivatives.
Figure 3
Figure 3
The superoxide radical-scavenging capacity of HACC and HACC derivatives.
Figure 4
Figure 4
The DPPH-radical scavenging capacity of HACC and HACC derivatives.
Figure 5
Figure 5
The antibacterial activity of HACC and HACC derivatives against S. aureus.
Figure 6
Figure 6
The antibacterial activity of HACC and HACC derivatives against E. coli.
Figure 7
Figure 7
The antifungal activity of HACC and HACC derivatives against B. cinerea.
Figure 8
Figure 8
The antifungal activity of HACC and HACC derivatives against Foc.
See this image and copyright information in PMC

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