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

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), w...

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Autores principales: Zhang, Jingjing, Tan, Wenqiang, Luan, Fang, Yin, Xiuli, Dong, Fang, Li, Qing, Guo, Zhanyong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6415387/
https://www.ncbi.nlm.nih.gov/pubmed/30966564
http://dx.doi.org/10.3390/polym10050530
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author Zhang, Jingjing
Tan, Wenqiang
Luan, Fang
Yin, Xiuli
Dong, Fang
Li, Qing
Guo, Zhanyong
author_facet Zhang, Jingjing
Tan, Wenqiang
Luan, Fang
Yin, Xiuli
Dong, Fang
Li, Qing
Guo, Zhanyong
author_sort Zhang, Jingjing
collection PubMed
description 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, (1)H NMR spectra, (13)C 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.
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spelling pubmed-64153872019-04-02 Synthesis of Quaternary Ammonium Salts of Chitosan Bearing Halogenated Acetate for Antifungal and Antibacterial Activities Zhang, Jingjing Tan, Wenqiang Luan, Fang Yin, Xiuli Dong, Fang Li, Qing Guo, Zhanyong Polymers (Basel) Article 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, (1)H NMR spectra, (13)C 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. MDPI 2018-05-15 /pmc/articles/PMC6415387/ /pubmed/30966564 http://dx.doi.org/10.3390/polym10050530 Text en © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Zhang, Jingjing
Tan, Wenqiang
Luan, Fang
Yin, Xiuli
Dong, Fang
Li, Qing
Guo, Zhanyong
Synthesis of Quaternary Ammonium Salts of Chitosan Bearing Halogenated Acetate for Antifungal and Antibacterial Activities
title Synthesis of Quaternary Ammonium Salts of Chitosan Bearing Halogenated Acetate for Antifungal and Antibacterial Activities
title_full Synthesis of Quaternary Ammonium Salts of Chitosan Bearing Halogenated Acetate for Antifungal and Antibacterial Activities
title_fullStr Synthesis of Quaternary Ammonium Salts of Chitosan Bearing Halogenated Acetate for Antifungal and Antibacterial Activities
title_full_unstemmed Synthesis of Quaternary Ammonium Salts of Chitosan Bearing Halogenated Acetate for Antifungal and Antibacterial Activities
title_short Synthesis of Quaternary Ammonium Salts of Chitosan Bearing Halogenated Acetate for Antifungal and Antibacterial Activities
title_sort synthesis of quaternary ammonium salts of chitosan bearing halogenated acetate for antifungal and antibacterial activities
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6415387/
https://www.ncbi.nlm.nih.gov/pubmed/30966564
http://dx.doi.org/10.3390/polym10050530
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