College of Material Science and Engineering, Huaqiao University, Engineering Research Center of Environment-Friendly Functional Materials, Ministry of Education, Xiamen 361021, PR China.
College of Material Science and Engineering, Huaqiao University, Engineering Research Center of Environment-Friendly Functional Materials, Ministry of Education, Xiamen 361021, PR China.
Int J Biol Macromol. 2024 Sep;276(Pt 1):133777. doi: 10.1016/j.ijbiomac.2024.133777. Epub 2024 Jul 10.
In this study, three types of dodecyl chitosan quaternary ammonium salts, each with different spacer groups were synthesized. These chitosan derivatives are N',N'-dimethyl-N'-dodecyl-ammonium chloride-N-amino-acetyl chitosan (DMDAC), N'-dodecyl-N-isonicotinyl chitosan chloride (DINCC) and N',N'-dimethyl-N'-dodecyl-ammonium chloride-N-benzoyl chitosan (DMDBC). The synthesized products were characterized using Fourier transform infrared spectrometers, nuclear magnetic resonance, thermogravimetric analysis, and elemental analysis. The antibacterial and antibiofilm activities against Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus) were investigated. The experimental results indicated that the introduction of hydrophobic groups of spacer groups could enhance the antibacterial and antibiofilm activities of the chitosan derivatives. The antibacterial rates of the chitosan derivatives were over 90 % for both E. coli and S. aureus at a concentration of 0.5 mg/mL. The chitosan derivatives removed >50 % of the mature biofilm of E. coli and over 90 % of the mature biofilm of S. aureus at a concentration of 2.5 mg/mL. Further, the synthesized chitosan derivatives were determined to be non-toxic to L929 cells. Among them, DMDBC exhibited the most promising overall performance and show potential for wide-ranging applications in food preservation, disinfectants, medical, and other fields.
在这项研究中，合成了三种类型的十二烷基壳聚糖季铵盐，它们都具有不同的间隔基。这些壳聚糖衍生物分别是 N',N'-二甲基-N'-十二烷基-氯化铵-N-氨乙酰壳聚糖（DMDAC）、N'-十二烷基-N-异烟酰基壳聚糖氯盐（DINCC）和 N',N'-二甲基-N-十二烷基-氯化铵-N-苯甲酰基壳聚糖（DMDBC）。采用傅里叶变换红外光谱仪、核磁共振、热重分析和元素分析对合成产物进行了表征。研究了它们对大肠杆菌（E. coli）和金黄色葡萄球菌（S. aureus）的抗菌和抗生物膜活性。实验结果表明，间隔基中引入疏水性基团可以增强壳聚糖衍生物的抗菌和抗生物膜活性。壳聚糖衍生物在浓度为 0.5mg/mL 时对大肠杆菌和金黄色葡萄球菌的抑菌率均超过 90%。壳聚糖衍生物在浓度为 2.5mg/mL 时可以去除>50%的成熟大肠杆菌生物膜和>90%的成熟金黄色葡萄球菌生物膜。此外，合成的壳聚糖衍生物对 L929 细胞无毒性。其中，DMDBC 表现出最有前途的综合性能，有望在食品保鲜、消毒剂、医疗等领域得到广泛应用。
