Synthesis of water soluble chitosan derivatives with halogeno-1,2,3-triazole and their antifungal activity.
Chitosan is an abundant and renewable polysaccharide, which exhibits attractive bioactivities and natural properties. Improvement such as chemical modification of chitosan is often performed prior to further utilization. Three novel water soluble chitosan derivatives containing 1,2,3- triazole with or without halogen was designed and synthesized. Their antifungal activity against three kinds of phytopathogens was estimated by hyphal measurement in vitro. The inhibitory property and water solubility of the synthesized chitosan derivatives exhibited a remarkable improvement over chitosan. It is hypothesized that thiazolyl groups enable the synthesized chitosan to possess obviously better antifungal activity. Moreover, CTCTS and BTCTS, which have halogens at the periphery of polymers, inhibited the growth of tested phytopathogens more effectively with inhibitory indices of 81-93% at 1.0mg/mL. The halogens could have a synergistic effect with triazole as they exhibited antifungal activity and electron-withdrawing capacity, which improve the antifungal activity of chitosan derivatives.
Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai, Shangdong 264003, China.
Qing
Q
Li
Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai, Shangdong 264003, China; Graduate School of Chinese Academy of Sciences, Beijing 100039, China.
Wenqiang
W
Tan
School of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, China.
Caili
C
Zhang
Alliance Pharma, Inc. 17 Lee Boulevard Malvern, PA 19355, USA.
Guodong
G
Gu
Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai, Shangdong 264003, China. Electronic address: zhanyongguo@hotmail.com.
Zhanyong
Z
Guo
D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D048271:Chitosan / Q000138:chemical synthesis* / Q000494:pharmacology*; D005658:Fungi / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D012995:Solubility; D017550:Spectroscopy, Fourier Transform Infrared; D014230:Triazoles / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
D000935:Antifungal Agents; D014230:Triazoles; D014867:Water; D048271:Chitosan
1,2,3-Triazole; Antifungal activity; Chitosan derivatives; Electron-withdrawing capacity; Halogens