Synthesis of Quaternary Ammonium Salts of Chitosan Bearing Halogenated Acetate for Antifungal and Antibacterial Activities.

Journal: Polymers
Published Date: May 15, 2018

Abstract

In this paper, quaternary ammonium salts of chitosan bearing halogenated acetate, including ,,-trimethyl chitosan chloroacetate (TMCSC), ,,-trimethyl chitosan dichloroacetate (TMCSDC), ,,-trimethyl chitosan trichloroacetate (TMCSTC), and ,,-trimethyl chitosan trifluoroacetate (TMCSTF), were prepared via ,,-trimethyl chitosan iodide (TMCSI). The obtained chitosan derivatives were characterized by FT-IR, ¹H NMR spectra, C NMR spectra, and elemental analysis. Their antifungal property against f. sp. cucumebrium Owen ( f. sp. cucumebrium Owen), (), and () were evaluated by hyphal measurement method at concentrations ranging from 0.08 mg/mL to 0.8 mg/mL. Meanwhile, two common bacteria, () and (), were selected as the model Gram-negative and Gram-positive bacteria to evaluate the antibacterial property of the chitosan derivatives by agar well diffusion method. The results showed that TMCSC, TMCSDC, TMCSTC, and TMCSTF had better antifungal and antibacterial activities than chitosan and TMCSI. In particular, a rule showed that the inhibitory activity decreased in the order: TMCSTF > TMCSTC > TMCSDC > TMCSC > TMCSI > chitosan, which was consistent with the electron-withdrawing property of different halogenated acetate. Apparently, the quaternary ammonium salts of chitosan with stronger electron withdrawing ability possessed relatively greater antifungal and antibacterial activities. This experiment provides a potentially feasible method for the further utilization of chitosan in fields of antifungal and antibacterial biomaterials.

Authors

  • Jingjing Zhang
    Department of Epidemiology and Medical Statistics School of Public Health, Guangdong Medical University, Dongguan, Guangdong, China.
  • Wenqiang Tan
    Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China. wqtan@yic.ac.cn.
  • Fang Luan
    Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China. fluan@yic.ac.cn.
  • Xiuli Yin
    Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China. xlyin@yic.ac.cn.
  • Fang Dong
    Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China. fdong@yic.ac.cn.
  • Qing Li
    Department of Internal Medicine, University of Michigan Ann Arbor, MI 48109, USA.
  • Zhanyong Guo
    Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China. zhanyongguo@hotmail.com.

Keywords

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