. 2018 Sep 5;16(9):315.

doi: 10.3390/md16090315.

Synthesis, Characterization, and Antifungal Property of Hydroxypropyltrimethyl Ammonium Chitosan Halogenated Acetates

Yingqi Mi^{1

2}, Wenqiang Tan^{3

4}, Jingjing Zhang^{5

6}, Lijie Wei^{7

8}, Yuan Chen^{9

10}, Qing Li¹¹, Fang Dong¹², Zhanyong Guo^{13

14}

Affiliations

¹ Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China. yqmi@yic.ac.cn.
² University of Chinese Academy of Sciences, Beijing 100049, China. yqmi@yic.ac.cn.
³ 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.
⁴ University of Chinese Academy of Sciences, Beijing 100049, China. wqtan@yic.ac.cn.
⁵ Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China. jingjingzhang@yic.ac.cn.
⁶ University of Chinese Academy of Sciences, Beijing 100049, China. jingjingzhang@yic.ac.cn.
⁷ Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China. ljwei@yic.ac.cn.
⁸ University of Chinese Academy of Sciences, Beijing 100049, China. ljwei@yic.ac.cn.
⁹ Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China. yuanchen@yic.ac.cn.
¹⁰ University of Chinese Academy of Sciences, Beijing 100049, China. yuanchen@yic.ac.cn.
¹¹ Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China. qli@yic.ac.cn.
¹² 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.
¹³ Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China. zhanyongguo@hotmail.com.
¹⁴ University of Chinese Academy of Sciences, Beijing 100049, China. zhanyongguo@hotmail.com.

PMID: 30189609
PMCID: PMC6165101
DOI: 10.3390/md16090315

Synthesis, Characterization, and Antifungal Property of Hydroxypropyltrimethyl Ammonium Chitosan Halogenated Acetates

Yingqi Mi et al. Mar Drugs. 2018.

. 2018 Sep 5;16(9):315.

doi: 10.3390/md16090315.

Authors

Yingqi Mi^{1

2}, Wenqiang Tan^{3

4}, Jingjing Zhang^{5

6}, Lijie Wei^{7

8}, Yuan Chen^{9

10}, Qing Li¹¹, Fang Dong¹², Zhanyong Guo^{13

14}

Affiliations

¹ Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China. yqmi@yic.ac.cn.
² University of Chinese Academy of Sciences, Beijing 100049, China. yqmi@yic.ac.cn.
³ 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.
⁴ University of Chinese Academy of Sciences, Beijing 100049, China. wqtan@yic.ac.cn.
⁵ Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China. jingjingzhang@yic.ac.cn.
⁶ University of Chinese Academy of Sciences, Beijing 100049, China. jingjingzhang@yic.ac.cn.
⁷ Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China. ljwei@yic.ac.cn.
⁸ University of Chinese Academy of Sciences, Beijing 100049, China. ljwei@yic.ac.cn.
⁹ Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China. yuanchen@yic.ac.cn.
¹⁰ University of Chinese Academy of Sciences, Beijing 100049, China. yuanchen@yic.ac.cn.
¹¹ Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China. qli@yic.ac.cn.
¹² 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.
¹³ Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China. zhanyongguo@hotmail.com.
¹⁴ University of Chinese Academy of Sciences, Beijing 100049, China. zhanyongguo@hotmail.com.

PMID: 30189609
PMCID: PMC6165101
DOI: 10.3390/md16090315

Abstract

Hydroxypropyltrimethyl ammonium chitosan halogenated acetates were successfully synthesized from six different haloacetic acids and hydroxypropyltrimethyl ammonium chloride chitosan (HACC) with high substitution degree, which are hydroxypropyltrimethyl ammonium chitosan bromacetate (HACBA), hydroxypropyltrimethyl ammonium chitosan chloroacetate (HACCA), hydroxypropyltrimethyl ammonium chitosan dichloroacetate (HACDCA), hydroxypropyltrimethyl ammonium chitosan trichloroacetate (HACTCA), hydroxypropyltrimethyl ammonium chitosan difluoroacetate (HACDFA), and hydroxypropyltrimethyl ammonium chitosan trifluoroacetate (HACTFA). These chitosan derivatives were synthesized by two steps: first, the hydroxypropyltrimethyl ammonium chloride chitosan was synthesized by chitosan and 3-chloro-2-hydroxypropyltrimethyl ammonium chloride. Then, hydroxypropyltrimethyl ammonium chitosan halogenated acetates were synthesized via ion exchange. The structures of chitosan derivatives were characterized by Fourier transform infrared spectroscopy (FTIR), ¹H Nuclear magnetic resonance spectrometer (¹H NMR), ¹³C Nuclear magnetic resonance spectrometer (¹³C NMR), and elemental analysis. Their antifungal activities against Colletotrichum lagenarium, Fusarium graminearum, Botrytis cinerea, and Phomopsis asparagi were investigated by hypha measurement in vitro. The results revealed that hydroxypropyltrimethyl ammonium chitosan halogenated acetates had better antifungal activities than chitosan and HACC. In particular, the inhibitory activity decreased in the order: HACTFA > HACDFA > HACTCA > HACDCA > HACCA > HACBA > HACC > chitosan, which was consistent with the electron-withdrawing property of different halogenated acetates. This experiment provides a potential idea for the preparation of new antifungal drugs by chitosan.

Keywords: antifungal activity; electronegativity; halogenated acetate; hydroxypropyltrimethyl ammonium chloride chitosan.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

**Scheme 1**
Synthesis routes for chitosan derivatives.

**Figure 1**
Fourier transform infrared spectroscopy (FTIR) spectra of chitosan and chitosan derivatives.

**Figure 2**
¹H Nuclear magnetic resonance spectrometer (¹H NMR) spectra of chitosan derivatives.

**Figure 3**
¹³C Nuclear magnetic resonance spectrometer (¹³C NMR) spectra of chitosan derivatives.

**Figure 4**
The antifungal activity of chitosan and chitosan derivatives against *Colletotrichum lagenarium*.

**Figure 5**
The antifungal activity of chitosan and chitosan derivatives against *Fusarium oxysporum*.

**Figure 6**
The antifungal activity of chitosan and chitosan derivatives against *Botrytis cinerea*.

**Figure 7**
The antifungal activity of chitosan and chitosan derivatives against *Phomopsis asparagi*.

See this image and copyright information in PMC

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References

1. Jones D.A., Bertazzoni S., Turo C.J., Syme R.A., Hane J.K. Bioinformatic prediction of plant-pathogenicity effector proteins of fungi. Curr. Opin. Microbiol. 2018;46:43–49. doi: 10.1016/j.mib.2018.01.017. - DOI - PubMed
1. Fan Z., Qin Y., Liu S., Xing R., Yu H., Chen X., Li K., Li P. Synthesis, characterization, and antifungal evaluation of diethoxyphosphoryl polyaminoethyl chitosan derivatives. Carbohydr. Polym. 2018;190:1–11. doi: 10.1016/j.carbpol.2018.02.056. - DOI - PubMed
1. Costa A.E.S., da Cunha F.S., Honorato A., Capucho A.S., Dias R., Borel J.C., Ishikawa F.H. Resistance to Fusarium Wilt in watermelon accessions inoculated by chlamydospores. Sci. Hortic. 2018;228:181–186. doi: 10.1016/j.scienta.2017.10.007. - DOI
1. Garmendia G., Umpierrez-Failache M., Ward T.J., Vero S. Development of a PCR-RFLP method based on the transcription elongation factor 1-alpha gene to differentiate Fusarium graminearum from other species within the Fusarium graminearum species complex. Int. J. Food. Microbiol. 2018;70:28–32. doi: 10.1016/j.fm.2017.08.020. - DOI - PubMed
1. Sevastos A., Kalampokis I.F., Panagiotopoulou A., Pelecanou M., Aliferis K.A. Implication of Fusarium graminearum primary metabolism in its resistance to benzimidazole fungicides as revealed by 1H NMR metabolomics. Pestic. Biochem. Phys. 2018;148:50–61. doi: 10.1016/j.pestbp.2018.03.015. - DOI - PubMed

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Synthesis, Characterization, and Antifungal Property of Hydroxypropyltrimethyl Ammonium Chitosan Halogenated Acetates

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Synthesis, Characterization, and Antifungal Property of Hydroxypropyltrimethyl Ammonium Chitosan Halogenated Acetates

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