从天然大分子获得的生物聚合物在具有高生物相容性和足够的生物降解性的材料中值得注意,与壳聚糖(CS)一样,使这种生物聚合物化合物成为合适的药物递送系统。在这里,使用2,3-二氯-1,4-萘醌(1,4-NQ)和1,2-萘醌-4-磺酸(1,2-NQ)的钠盐合成化学修饰的CS,通过三种不同的方法生产1,4-NQ-CS和1,2-NQ-CS,使用乙醇和水的混合物(EtOH:H2O),EtOH:H2O加三乙胺和二甲基甲酰胺。使用水/乙醇和三乙胺作为1,4-NQ-CS的碱达到0.12的最高取代度(SD),而1,2-NQ-CS为0.54。所有合成产物均通过FTIR表征,元素分析,SEM,TGA,DSC,拉曼,和固态核磁共振,确认用1,4-NQ和1,2-NQ修饰的CS。壳聚糖接枝到1,4-NQ对金黄色葡萄球菌和表皮葡萄球菌显示出优异的抗菌活性,并具有改善的细胞毒性和功效,高治疗指数表明,确保安全应用于人体组织。尽管1,4-NQ-CS抑制人乳腺癌细胞(MDA-MB-231)的生长,它伴有细胞毒性,应谨慎考虑。本文报道的发现强调,1,4-NQ嫁接的CS可能有助于保护受伤组织免受细菌侵害,常见于皮肤感染,直到组织完全恢复.
Biopolymers obtained from natural macromolecules are noteworthy among materials presenting high biocompatibility and adequate biodegradability, as is the case of chitosan (CS), making this biopolymeric compound a suitable drug delivery system. Herein, chemically-modified CS were synthetized using 2,3-dichloro-1,4-naphthoquinone (1,4-NQ) and the sodium salt of 1,2-naphthoquinone-4-sulfonic acid (1,2-NQ), producing 1,4-NQ-CS and 1,2-NQ-CS by three different methods, employing an ethanol and water mixture (EtOH:H2O), EtOH:H2O plus triethylamine and dimethylformamide. The highest substitution degree (SD) of 0.12 was achieved using water/ethanol and triethylamine as the base for 1,4-NQ-CS and 0.54 for 1,2-NQ-CS. All synthesized products were characterized by FTIR, elemental analysis, SEM, TGA, DSC, Raman, and solid-state NMR, confirming the CS modification with 1,4-NQ and 1,2-NQ. Chitosan grafting to 1,4-NQ displayed superior antimicrobial activities against Staphylococcus aureus and Staphylococcus epidermidis associated with improved cytotoxicity and efficacy, indicated by high therapeutic indices, ensuring safe application to human tissue. Although 1,4-NQ-CS inhibited the growth of human mammary adenocarcinoma cells (MDA-MB-231), it is accompanied by cytotoxicity and should be considered with caution. The findings reported herein emphasize that 1,4-NQ-grafted CS may be useful in protecting injured tissue against bacteria, commonly found in skin infections, until complete tissue recovery.