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Enhanced antioxidant and antifungal activity of chitosan derivatives bearing 6-O-imidazole-based quaternary ammonium salts

Wei, Lijie, Li, Qing, Chen, Yuan, Zhang, Jingjing, Mi, Yingqi, Dong, Fang, Lei, Chunqing, Guo, Zhanyong
Carbohydrate polymers 2019 v.206 pp. 493-503
2,2-diphenyl-1-picrylhydrazyl, Botrytis cinerea, Fourier transform infrared spectroscopy, Fusarium graminearum, ammonium salts, antifungal properties, antioxidant activity, biocompatible materials, chitosan, cytotoxicity, free radicals, hydroxyl radicals, nuclear magnetic resonance spectroscopy, quaternary ammonium compounds, superoxide anion
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 1H 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.