酚基壳聚糖季铵盐的结构对抗菌和抗生物被膜活性的影响

Effect of Structure of Phenol-Based Chitosan Quaternary Ammonium Salt on Antibacterial and Antibiofilm Activities

制备邻羟基苯甲酰化壳聚糖(OPC)、间羟基苯甲酰化壳聚糖(MPC)、对羟基苯甲酰化壳聚糖(PPC)、3,5-二羟基苯甲酰化壳聚糖(DPC)、3,4,5-三羟基苯甲酰化壳聚糖(TPC)、O-(2-羟丙基三甲基氯化铵)壳聚糖(QACS)和O-(2-羟丙基三甲基氯化铵)-N-对羟基苯甲酰化壳聚糖(QAPPC)7种壳聚糖衍生物,采用核磁共振氢谱和元素分析表征产物的结构,并测试产物的抗菌活性和抗生物被膜活性。结果表明:产物的抗菌活性和抗生物被膜活性排序为PPC>OPC>MPC;质量浓度为0.5 mg·mL^(-1)的PPC对大肠杆菌(E.coli)、金黄色葡萄球菌(S.aureus)的抑菌率分别为78.2%,100.0%,质量浓度为2.5 mg·mL^(-1)的PPC对E.coli,S.aureus形成的生物被膜的清除率分别为75.3%,87.7%;将对羟基苯甲酸接枝到QACS的氨基上,制备的QAPPC的抗菌活性和抗生物被膜活性均优于QACS和PPC,酚基和季铵盐具有协同抗菌效果;质量浓度为0.5 mg·mL^(-1)的QAPPC对E.coli,S.aureus的抑菌率分别为83.3%,100.0%,质量浓度为2.5 mg·mL^(-1)的QAPPC对E.coli,S.aureus生物被膜的清除率分别为77.4%,92.4%。

Seven chitosan derivatives were prepared including o-hydroxybenzoylate chitosan(OPC),m-hydroxybenzoylated chitosan(MPC),p-hydroxybenzoylated chitosan(PPC),3,5-dihydroxybenzoylated chitosan(DPC),3,4,5-trihydroxybenzoylated chitosan(TPC),O-(2-hydroxypropyltrimethylammonium chloride)chitosan(QACS)and O-(2-hydroxypropyltrimethylammonium chloride)-N-p-hydroxybenzoylated chitosan(QAPPC).Nuclear magnetic resonance spectra and elemental analysis were used to characterize the structure of the product,and the antibacterial activity and antibiofilm activity of the product were tested.The results showed that the order of antibacterial activity and antibiofilm activity of the product was PPC>OPC>MPC.The antibacterial rates of PPC at mass concentration of 0.5 mg·mL^(-1) against Escherichia coli(E.coli)and Staphylococcus aureus(S.aureus)were 78.2%and 100.0%,respectively.The biofilm removal rates of PPC at mass concentration of 2.5 mg·mL^(-1) against E.coli and S.aureus were 75.3%and 87.7%,respectively.4-hydroxybenzoic acid was grafted onto the amino group of QACS,the antibacterial activity and antibiofilm activity of the prepared QAPPC were both superior to those of QACS and PPC,and the phenolic group and quaternary ammonium salts had synergistic antibacterial effects.The antibacterial rates of QAPPC at mass concentration of 0.5 mg·mL^(-1) against E.coli and S.aureus were 83.3%and 100.0%,respectively,and the biofilm removal rates of QAPPC at mass concentration of 2.5 mg·mL^(-1) against E.coli and S.aureus were 77.4%and 92.4%,respectively.