Chitosan-gallic acid conjugate with enhanced functional properties and synergistic wound healing effect

IF 2.4 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

Carbohydrate Research Pub Date : 2025-04-18 DOI:10.1016/j.carres.2025.109496

Katsiaryna Khainskaya , Kseniya Hileuskaya , Viktoryia Nikalaichuk , Alena Ladutska , Oliy Akhmedov , Nadjiye Abrekova , Lijun You , Ping Shao , Munkhjargal Odonchimeg

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Abstract

Chitosan-gallic acid conjugates were synthesized by carbodiimide method and characterized by physicochemical methods (UV–vis, FTIR, ¹H NMR, TGA). The FTIR and NMR assays confirmed that the chemical interaction occurred solely due to the formation of an amide bond. It was established that by varying the ratio of the components during synthesis it is possible to obtain conjugates with desired conjugation ratio, grafting efficiency and gallic acid content up to 8.09 ± 1.72 %, 70.51 ± 9.45 % and 79.9 ± 2.4 μg gallic acid/mg chitosan, respectively. Chitosan-gallic acid conjugate with a 5 % conjugation ratio demonstrated excellent antioxidant properties: the IC50 value for ABTS radical scavenging activity was 0.0073 ± 0.0001 mg/mL. In vitro tests showed that conjugation of chitosan with gallic acid provided the antiglycemic activity of the material and its good biocompatibility. A low level of cytotoxicity was recorded in the HaCaT cell line model (IC50 was 1030.4 μg/mL). The received eco-friendly chitosan-gallic acid conjugate effectively inhibited the growth of thermophilic spore-forming bacteria G. thermodenitrificans and the resistant to classical antibiotics strain A. palidus. The results of an in vivo comparative analysis showed that chitosan-gallic acid conjugate had excellent wound healing properties due to the synergism of the polysaccharide and the natural antioxidant.

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壳聚糖-没食子酸缀合物具有增强的功能特性和协同伤口愈合效果

采用碳二亚胺法合成了壳聚糖-没食子酸缀合物，并用理化方法（UV-vis、FTIR、1H NMR、TGA）对其进行了表征。红外光谱和核磁共振分析证实，化学相互作用的发生完全是由于酰胺键的形成。结果表明，通过改变合成过程中各组分的配比，可以得到符合要求的共轭物，共轭率为8.09±1.72%，接枝效率为70.51±9.45%，没食子酸含量为79.9±2.4 μg /mg壳聚糖。偶联率为5%的壳聚糖-没食子酸偶联物具有良好的抗氧化性能：清除ABTS自由基的IC50值为0.0073±0.0001 mg/mL。体外实验表明，壳聚糖与没食子酸结合后具有良好的降糖活性和生物相容性。HaCaT细胞系模型细胞毒性较低，IC50为1030.4 μg/mL。所获得的友好型壳聚糖-没食子酸偶联物能有效抑制嗜热孢子形成细菌G.热反硝化菌和耐经典抗生素菌株A. palidus的生长。体内比较分析结果表明，壳聚糖-没食子酸缀合物由于其多糖和天然抗氧化剂的协同作用，具有良好的伤口愈合性能。

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来源期刊

Carbohydrate Research 化学-生化与分子生物学

CiteScore

5.00

自引率

3.20%

发文量

183

审稿时长

3.6 weeks

期刊介绍： Carbohydrate Research publishes reports of original research in the following areas of carbohydrate science: action of enzymes, analytical chemistry, biochemistry (biosynthesis, degradation, structural and functional biochemistry, conformation, molecular recognition, enzyme mechanisms, carbohydrate-processing enzymes, including glycosidases and glycosyltransferases), chemical synthesis, isolation of natural products, physicochemical studies, reactions and their mechanisms, the study of structures and stereochemistry, and technological aspects. Papers on polysaccharides should have a "molecular" component; that is a paper on new or modified polysaccharides should include structural information and characterization in addition to the usual studies of rheological properties and the like. A paper on a new, naturally occurring polysaccharide should include structural information, defining monosaccharide components and linkage sequence. Papers devoted wholly or partly to X-ray crystallographic studies, or to computational aspects (molecular mechanics or molecular orbital calculations, simulations via molecular dynamics), will be considered if they meet certain criteria. For computational papers the requirements are that the methods used be specified in sufficient detail to permit replication of the results, and that the conclusions be shown to have relevance to experimental observations - the authors'' own data or data from the literature. Specific directions for the presentation of X-ray data are given below under Results and "discussion".