Cyclization Reaction of Acyl Thiourea Chitosan: Enhanced Antifungal Properties via Structural Optimization

In this study, 3-methyl-1,2,4-triazolyl chitosan (MTACS) and 3-chloromethyl-1,2,4-triazolyl chitosan (CMTACS) were prepared via cyclization of acyl thiourea chitosan (TUCS). Their structures were confirmed by FT-IR, (1)H-NMR, elemental analysis, DSC, XRD, and SEM. The conformations were predicted us...

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Autores principales: Qin, Yukun, Liu, Weixiang, Xing, Ronge, Liu, Song, Li, Kecheng, Li, Pengcheng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6017949/
https://www.ncbi.nlm.nih.gov/pubmed/29509712
http://dx.doi.org/10.3390/molecules23030594
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author Qin, Yukun
Liu, Weixiang
Xing, Ronge
Liu, Song
Li, Kecheng
Li, Pengcheng
author_facet Qin, Yukun
Liu, Weixiang
Xing, Ronge
Liu, Song
Li, Kecheng
Li, Pengcheng
author_sort Qin, Yukun
collection PubMed
description In this study, 3-methyl-1,2,4-triazolyl chitosan (MTACS) and 3-chloromethyl-1,2,4-triazolyl chitosan (CMTACS) were prepared via cyclization of acyl thiourea chitosan (TUCS). Their structures were confirmed by FT-IR, (1)H-NMR, elemental analysis, DSC, XRD, and SEM. The conformations were predicted using the Gaussian 09 program. Additionally, the antifungal properties of MTACS and CMTACS against Stemphylium solani weber (S. solani), Alternaria porri (A. porri), and Gloeosporium theae-sinensis (G. theae-sinensis) were assayed in vitro and ranged from 250 μg/mL to 1000 μg/mL. The results showed that MTACS and CMTACS exhibited enhanced inhibitory effect on the selected fungi compared to the original chitosan and TUCS. In particular, they displayed better antifungal activities against A. porri and G. theae-sinensis than that of the positive control, Triadimefon. The findings described here may lead to them being used as antifungal agents for crop protection.
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spelling pubmed-60179492018-11-13 Cyclization Reaction of Acyl Thiourea Chitosan: Enhanced Antifungal Properties via Structural Optimization Qin, Yukun Liu, Weixiang Xing, Ronge Liu, Song Li, Kecheng Li, Pengcheng Molecules Article In this study, 3-methyl-1,2,4-triazolyl chitosan (MTACS) and 3-chloromethyl-1,2,4-triazolyl chitosan (CMTACS) were prepared via cyclization of acyl thiourea chitosan (TUCS). Their structures were confirmed by FT-IR, (1)H-NMR, elemental analysis, DSC, XRD, and SEM. The conformations were predicted using the Gaussian 09 program. Additionally, the antifungal properties of MTACS and CMTACS against Stemphylium solani weber (S. solani), Alternaria porri (A. porri), and Gloeosporium theae-sinensis (G. theae-sinensis) were assayed in vitro and ranged from 250 μg/mL to 1000 μg/mL. The results showed that MTACS and CMTACS exhibited enhanced inhibitory effect on the selected fungi compared to the original chitosan and TUCS. In particular, they displayed better antifungal activities against A. porri and G. theae-sinensis than that of the positive control, Triadimefon. The findings described here may lead to them being used as antifungal agents for crop protection. MDPI 2018-03-06 /pmc/articles/PMC6017949/ /pubmed/29509712 http://dx.doi.org/10.3390/molecules23030594 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
Qin, Yukun
Liu, Weixiang
Xing, Ronge
Liu, Song
Li, Kecheng
Li, Pengcheng
Cyclization Reaction of Acyl Thiourea Chitosan: Enhanced Antifungal Properties via Structural Optimization
title Cyclization Reaction of Acyl Thiourea Chitosan: Enhanced Antifungal Properties via Structural Optimization
title_full Cyclization Reaction of Acyl Thiourea Chitosan: Enhanced Antifungal Properties via Structural Optimization
title_fullStr Cyclization Reaction of Acyl Thiourea Chitosan: Enhanced Antifungal Properties via Structural Optimization
title_full_unstemmed Cyclization Reaction of Acyl Thiourea Chitosan: Enhanced Antifungal Properties via Structural Optimization
title_short Cyclization Reaction of Acyl Thiourea Chitosan: Enhanced Antifungal Properties via Structural Optimization
title_sort cyclization reaction of acyl thiourea chitosan: enhanced antifungal properties via structural optimization
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6017949/
https://www.ncbi.nlm.nih.gov/pubmed/29509712
http://dx.doi.org/10.3390/molecules23030594
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