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.
Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai, 264003, China.
Carbohydr Polym. 2019 Feb 15;206:493-503. doi: 10.1016/j.carbpol.2018.11.022. Epub 2018 Nov 13.
In this paper, a series of 6-O-imidazole-based quaternary ammonium chitosan derivatives via 6-O-chloroacetyl chitosan (CAClC) were successfully designed and synthesized. Detailed structural characterization was carried out by means of FT-IR and H NMR spectroscopy, and elemental analysis. Furthermore, the antioxidant property against hydroxyl radicals, superoxide radicals, and DPPH radicals was evaluated in vitro. 2-(N,N,N-trimethyl)-6-O-(2-aminobenzimidazole)acetyl chitosan chloride (2NPhMC) and 2-(N,N,N-trimethyl)-6-O-(1-butylimidazole)acetyl chitosan chloride (NBMC) showed more than 90% scavenging indices at 1.6 mg/mL. Besides, the antifungal activity against Botrytis cinerea and Gibberella zeae was estimated using in vitro MIC and hypha measurements. Most of the quaternized chitosan derivatives especially with the long length alkyl chain and primary amino group showed an inhibitory index of > 85% at 1.0 mg/mL against Botrytis cinerea. Besides, the cytotoxicity of chitosan and all the quaternized chitosan derivatives was evaluated in vitro on HaCaT cells and all the quaternized chitosan derivatives bearing 6-O-imidazole exhibited low cytotoxicity. These results suggested that chitosan derivatives bearing 6-O-imidazole-based quaternary ammonium salts may be used as good biomaterials.
本文通过 6-O-氯乙酰壳聚糖（CAClC）成功设计和合成了一系列 6-O-咪唑基季铵化壳聚糖衍生物。详细的结构表征通过傅里叶变换红外光谱（FT-IR）和核磁共振光谱（H NMR）以及元素分析进行。此外，还在体外评估了其对羟基自由基、超氧自由基和 DPPH 自由基的抗氧化性能。2-（N，N，N-三甲基）-6-O-（2-氨基苯并咪唑）乙酰壳聚糖氯化物（2NPhMC）和 2-（N，N，N-三甲基）-6-O-（1-丁基咪唑）乙酰壳聚糖氯化物（NBMC）在 1.6mg/mL 时的清除率超过 90%。此外，还通过体外 MIC 和菌丝测量评估了它们对灰葡萄孢和禾谷镰刀菌的抗真菌活性。大多数季铵化壳聚糖衍生物，特别是具有长链烷基和伯氨基的季铵化壳聚糖衍生物，在 1.0mg/mL 时对灰葡萄孢的抑制指数>85%。此外，还在 HaCaT 细胞上评估了壳聚糖及其所有季铵化壳聚糖衍生物的体外细胞毒性，所有带有 6-O-咪唑的季铵化壳聚糖衍生物均表现出低细胞毒性。这些结果表明，带有 6-O-咪唑基季铵盐的壳聚糖衍生物可能可用作良好的生物材料。
