title: Novel 1,2,3-triazolium-functionalized starch derivatives: Synthesis, characterization, and evaluation of antifungal property.
abstract: Four novel 1,2,3-triazolium-functionalized starch derivatives were synthesized by N-alkylating the precursor starch derivatives with 1,2,3-triazole with iodomethane based on cuprous-catalyzed azide-alkyne cycloaddition (CuAAC). The detailed structural characterization was investigated by means of FTIR, UV-vis,1H NMR, and13C NMR spectra. The antifungal activities of starch derivatives against Colletotrichum lagenarium, Fusarium oxysporum, and Watermelon fusarium, were then assayed by hypha measurement in vitro. The fungicidal assessment revealed that compared with starch and starch derivatives with 1,2,3-triazole, 1,2,3-triazolium-functionalized starch derivatives displayed tremendously enhanced antifungal activity. Especially, the inhibitory indices of 6-(4-hydroxymethyl-3-methyl-1,2,3-triazolium-1-yl)-6-deoxy starch iodine (2a) with against the tested plant threatening fungi attained 70% above at 1.0mg/mL. It was also found that their antifungal activity profiles were dependent on the variation in alkyl chain length. As novel 1,2,3-triazolium-functionalized starch derivatives could be prepared efficiently and exhibited superduper antifungal activity, this synthetic strategy might provide an effective way and notion to prepare novel antifungal biomaterials.
authors.affiliation: Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China; University of Chinese Academy of Sciences, Beijing 100049, China.
authors.forename: Wenqiang
authors.initials: W
authors.lastname: Tan
authors.affiliation: Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China.
authors.forename: Qing
authors.initials: Q
authors.lastname: Li
authors.affiliation: Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China.
authors.forename: Fang
authors.initials: F
authors.lastname: Dong
authors.affiliation: College of Life Sciences, Yantai University, Yantai 264005, China.
authors.forename: Shuai
authors.initials: S
authors.lastname: Qiu
authors.affiliation: Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China; University of Chinese Academy of Sciences, Beijing 100049, China.
authors.forename: Jingjing
authors.initials: J
authors.lastname: Zhang
authors.affiliation: Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China; University of Chinese Academy of Sciences, Beijing 100049, China. Electronic address: zhanyongguo@hotmail.com.
authors.forename: Zhanyong
authors.initials: Z
authors.lastname: Guo
mesh_terms: D020231:Colletotrichum / Q000187:drug effects; D005659:Fungicides, Industrial / Q000737:chemistry*; D005670:Fusarium / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D013213:Starch / Q000737:chemistry*; D014230:Triazoles / Q000737:chemistry*
chemical_list: D005659:Fungicides, Industrial; D014230:Triazoles; D013213:Starch
keywords: 1,2,3-Triazolium; 2-Propyn-1-ol (PubChemCID: 7859); 3-Butyn-1-ol (PubChemCID: 13566); 4-Pentyn-1-ol (PubChemCID: 79346); 5-Hexyn-1-ol (PubChemCID: 70234); Antifungal activity; Characterization; Chemical modification; Click chemistry; Iodomethane (PubChemCID: 6328); N-Bromosuccinimide (PubChem CID: 67184); Sodium azide (PubChem CID: 33557); Soluble starch (PubChem CID: 439341); Starch; Triphenylphosphine (PubChem CID: 11776)