Water-Soluble Quaternary and Protonable Basic Chitotriazolans: Synthesis by Click Chemistry Conversion of Chitosan Azides and Investigation of Antibacterial Activity

被引:4
作者
Rathinam, Sankar [1 ]
Magdadaro, Romano [1 ]
Hjalmarsdottir, Martha A. [2 ]
Masson, Mar [1 ]
机构
[1] Univ Iceland, Fac Pharmaceut Sci, Sch Hlth Sci, Hofsvallagata 53, IS-107 Reykjavik, Iceland
[2] Univ Iceland, Fac Med, Sch Hlth Sci, Dept Biomed Sci, Hringbraut 31, IS-101 Reykjavik, Iceland
关键词
chitosan; click chemistry; triazole; antibacterial activity; DERIVATIVES; LIGATION; DESIGN; CHITIN;
D O I
10.3390/jfb15030063
中图分类号
R318 [生物医学工程];
学科分类号
0831 ;
摘要
The azide transfer reaction and copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) can be used to convert the amino groups in chitosan to triazole 1,2,3-moieties. The resulting polymer has been named chitotriazolan. This synthesis was performed with six different quaternary ammonium alkynes and three amine alkynes to obtain a series of nine water-soluble chitotriazolan derivatives. The structure and complete conversion of the azide were confirmed by FT-IR and proton NMR spectroscopy. The derivatives were investigated for antibacterial activity against S. aureus, E. faecalis, E. coli, and P. aeruginosa. The activity of the quaternized chitotriazolan derivatives varied depending on the structure of the quaternary moiety and the species of bacteria. The basic protonable derivatives were less active or inactive against the bacteria.
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页数:14
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