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. 2018 May 15;10(5):530.
doi: 10.3390/polym10050530.

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

Jingjing Zhang  1   2 , Wenqiang Tan  3   4 , Fang Luan  5   6 , Xiuli Yin  7 , Fang Dong  8 , Qing Li  9 , Zhanyong Guo  10   11
Affiliations

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

Jingjing Zhang et al. Polymers (Basel). .

Abstract

In this paper, quaternary ammonium salts of chitosan bearing halogenated acetate, including N,N,N-trimethyl chitosan chloroacetate (TMCSC), N,N,N-trimethyl chitosan dichloroacetate (TMCSDC), N,N,N-trimethyl chitosan trichloroacetate (TMCSTC), and N,N,N-trimethyl chitosan trifluoroacetate (TMCSTF), were prepared via N,N,N-trimethyl chitosan iodide (TMCSI). The obtained chitosan derivatives were characterized by FT-IR, ¹H NMR spectra, 13C NMR spectra, and elemental analysis. Their antifungal property against Fusarium oxysporum f. sp. cucumebrium Owen (F. oxysporum f. sp. cucumebrium Owen), Botrytis cinerea (B. cinerea), and Phomopsis asparagi (P. asparagi) were evaluated by hyphal measurement method at concentrations ranging from 0.08 mg/mL to 0.8 mg/mL. Meanwhile, two common bacteria, Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus), 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.

Keywords: antibacterial activity; antifungal activity; characterization; halogenated acetate; quaternary ammonium salts of chitosan.

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Conflict of interest statement

The authors declare that there is no conflict of interest.

Figures

Scheme 1
Scheme 1
Synthesis pathway of chitosan derivatives.
Figure 1
Figure 1
FT-IR spectra of chitosan, TMCSI, TMCSC, TMCSDC, TMCSTC, and TMCSTF.
Figure 2
Figure 2
1H NMR spectra of TMCSI, TMCSC, TMCSDC, TMCSTC, and TMCSTF.
Figure 3
Figure 3
13C NMR spectra of TMCSI, TMCSC, TMCSDC, TMCSTC, and TMCSTF.
Figure 4
Figure 4
The antifungal activity of chitosan and chitosan derivatives against F. oxysporum f. sp. cucumebrium Owen.
Figure 5
Figure 5
The antifungal activity of chitosan and chitosan derivatives against B. cinerea.
Figure 6
Figure 6
The antifungal activity of chitosan and chitosan derivatives against P. asparagi.
See this image and copyright information in PMC

References

    1. Zhang J., Tan W., Zhang Z., Song Y., Li Q., Dong F., Guo Z. Synthesis, characterization, and the antifungal activity of chitosan derivatives containing urea groups. Int. J. Biol. Macromol. 2018;109:1061–1067. doi: 10.1016/j.ijbiomac.2017.11.092. - DOI - PubMed
    1. Asghar M.A., Zahir E., Shahid S.M., Khan M.N., Asghar M.A., Iqbal J., Walker G. Iron, copper and silver nanoparticles: Green synthesis using green and black tea leaves extracts and evaluation of antibacterial, antifungal and aflatoxin B 1 adsorption activity. LWT. 2018;90:98–107. doi: 10.1016/j.lwt.2017.12.009. - DOI
    1. Yang G., Jin Q., Xu C., Fan S., Wang C., Xie P. Synthesis, characterization and antifungal activity of coumarin-functionalized chitosan derivatives. Int. J. Biol. Macromol. 2018;106:179–184. doi: 10.1016/j.ijbiomac.2017.08.009. - DOI - PubMed
    1. Lagrouh F., Dakka N., Bakri Y. The antifungal activity of Moroccan plants and the mechanism of action of secondary metabolites from plants. J. Mycol. Med. 2017;27:303–311. doi: 10.1016/j.mycmed.2017.04.008. - DOI - PubMed
    1. Lukowska-Chojnacka E., Mierzejewska J., Milner-Krawczyk M., Bondaryk M., Staniszewska M. Synthesis of novel tetrazole derivatives and evaluation of their antifungal activity. Bioorg. Med. Chem. 2016;24:6058–6065. doi: 10.1016/j.bmc.2016.09.066. - DOI - PubMed

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