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Synthesis, characterization, and antibacterial activity of N,O-quaternary ammonium chitosan
Authors:Xu Tao  Xin Meihua  Li Mingchun  Huang Huili  Zhou Shengquan  Liu Juezhao
Affiliation:aCollege of Material Science and Engineering, Huaqiao University, Xiamen 361021, China;bCollege of Chemical Engineering, Huaqiao University, Xiamen 361021, China
Abstract:N,N,N-Trimethyl O-(2-hydroxy-3-trimethylammonium propyl) chitosans (TMHTMAPC) with different degrees of O-substitution were synthesized by reacting O-methyl-free N,N,N-trimethyl chitosan (TMC) with 3-chloro-2-hydroxy-propyl trimethyl ammonium chloride (CHPTMAC). The products were characterized by 1H NMR, FTIR and TGA, and investigated for antibacterial activity against Staphylococcus aureus and Escherichia coli under weakly acidic (pH 5.5) and weakly basic (pH 7.2) conditions. TMHTMAPC exhibited enhanced antibacterial activity compared with TMC, and the activity of TMHTMAPC increased with an increase in the degree of substitution. Divalent cations (Ba2+ and Ca2+) strongly reduced the antibacterial activity of chitosan, O-carboxymethyl chitosan and N,N,N-trimethyl-O-carboxymethyl chitosan, but the repression on the antibacterial activity of TMC and TMHTMAPC was weaker. This indicates that the free amino group on chitosan backbone is the main functional group interacting with divalent cations. The existence of 100 mM Na+ slightly reduced the antibacterial activity of both chitosan and its derivatives.
Keywords:Chitosan   N,N,N-Trimethyl chitosan   Quaternary ammonium chitosan   Antibacterial activity
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