| 引用本文: | 计雨婷,王林卿,陈秋红,董方,孙明志,唐红霞,郭占勇.壳聚糖喹诺酮类衍生物的制备及生物活性研究[J].海洋科学,2024,48(11):5-. |
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| 壳聚糖喹诺酮类衍生物的制备及生物活性研究 |
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计雨婷1,2, 王林卿1,2, 陈秋红1, 董方1, 孙明志3, 唐红霞3, 郭占勇1
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1.中国科学院烟台海岸带研究所, 山东 烟台 264003;2.中国科学院大学, 北京 100049;3.烟台富慧农业科技有限公司, 山东 烟台 264003
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| 摘要: |
| 喹诺酮类抗生素是一类新合成的抗菌药,其母核结构上的游离羧基可为多种反应提供位点。通过对羧基修饰,接枝壳聚糖,得到一系列喹诺酮壳聚糖盐类衍生物和酰化衍生物。利用红外光谱、核磁共振氢谱及氟谱对衍生物进行结构表征,并对合成的衍生物进行抑菌活性分析和细胞毒性检测。结果表明,相较于壳聚糖,所合成的壳聚糖喹诺酮类衍生物的抑菌活性显著提升。其中,环丙沙星壳聚糖盐与原料环丙沙星抑菌效果相近,对大肠杆菌的最小抑菌浓度(MIC)为0.122 1 μg∙mL–1,最小杀菌浓度(MBC)为0.122 1 μg∙mL–1,对金黄色葡萄球菌的MIC为0.488 3 μg∙mL–1,MBC为1.953 μg∙mL–1。同时,相较于喹诺酮,所合成的壳聚糖喹诺酮类衍生物的细胞毒性明显降低。除喹诺酮壳聚糖盐类衍生物在最大测试浓度(1 000 μg∙mL–1)下处理的细胞存活率低于80%,其他测试浓度下所有衍生物均表现出低细胞毒或无毒。因此,壳聚糖结构的引入,在降低喹诺酮细胞毒性的同时,可使衍生物保持较高的抑菌活性,壳聚糖喹诺酮类衍生物的合成对于喹诺酮类抗生素的后续研究开发及临床应用具有重要的理论意义与应用价值。 |
| 关键词: 壳聚糖衍生物 喹诺酮 抑菌活性 细胞毒性 |
| DOI：10.11759/hykx20240201001 |
| 分类号:P745 |
| 基金项目:2022年度山东省中央引导地方科技发展资金项目(YDZX2022007) |
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| Synthesis and biological activities of quinolone-modified chitosan derivatives |
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JI Yuting1,2, WANG Linqing1,2, CHEN Qiuhong1, DONG Fang1, SUN Mingzhi3, TANG Hongxia3, GUO Zhanyong1
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1.Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China;2.University of Chinese Academy of Sciences, Beijing 100049, China;3.Yantai Fuhui Agricultural Technology Co., Ltd, Yantai 264003, China
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| Abstract: |
| Quinolones are synthetic antimicrobial agents with free carboxyl groups that can participate in multiple reactions. Herein, derivatives of quinolone-grafted chitosan were synthesized and characterized by FT-IR, 1H NMR, and 19F NMR. The antibacterial and cytotoxic activities of the chitosan derivatives were ascertained. The antibacterial activities of the chitosan derivatives (CS-LEV, CS-CIP, CS-NOR, CSLEV, CSCIP, and CSNOR) considerably improved. Specifically, the MIC and MBC of CSCIP against E. coli and S. aureus were 0.1221, 0.4883, 0.1221, and 1.953 μg∙mL−1, respectively. This result indicated that the potency of CSCIP was similar to that of ciprofloxacin. Moreover, the cytotoxicity of the chitosan quinolone derivatives markedly diminished. Specifically, except for the influence of CSLEV, CSCIP, and CSNOR at the maximum tested concentration (1, 000 μg∙mL−1) on cell viability, which was <80%, all derivatives were low- or nonpoisonous. In conclusion, the addition of chitosan reduced cytotoxicity while maintaining the high antibacterial activity of chitosan derivatives. The preparation of chitosan quinolone derivatives for subsequent development and clinical research has crucial theoretical significance and application value. |
| Key words: chitosan derivatives quinolones antibacterial activity cytotoxicity |
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