Journal of Hebei University (Natural Science Edition) ›› 2020, Vol. 40 ›› Issue (2): 151-160.DOI: 10.3969/j.issn.1000-1565.2020.02.007

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Preparation and biological evaluation of fluorescently labeled piperazine antibacterial polymer

SUN Zhuxing,DENG Kuilin,LIU Na,ZHANG Huanyu,LIU Hongmei   

  1. Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of Ministry of Education, College of Chemistry and Environment Science, Hebei University, Baoding 071002, China
  • Received:2019-07-15 Online:2020-03-25 Published:2020-03-25

Abstract: Considering at poor biocompatibility,no fluorescent labeling,and bacterial resistance for the antibacterial material,combining the advantages of polymer antibacterial materials,1,4 bis-(3-aminopropyl)piperazine,7-N,N-diethylamino-3-aldehyde coumarin,Dibutyrate with a molecular weight of 800 polyethylene glycol(PB),tert-butyl isonitrile and benzaldehyde are used as raw materials to obtain a novel fluorescently labeled antibacterial polymer(PC)with unique structure through high efficiency and atomic economic multi-component reaction-Ugi reaction.The polymer has been characterized by 1H NMR and FTIR.the antibacterial activity of PC against Staphylococcus aureus and Escherichia coli was examined by filter paper method and bacterial growth curve method.Then the biocompatibility of PC was evaluated by MTT and AM-PI double staining method.Live cell imaging studies of PC were performed by laser confocal microscopy.- DOI:10.3969/j.issn.1000-1565.2020.02.007荧光标记哌嗪抗菌聚合物的制备及生物学评价孙竹兴,邓奎林,刘娜,张欢雨,刘红梅(河北大学 化学与环境科学学院 药物化学与分子诊断教育部重点实验室,河北 保定 071002)摘 要:针对目前抗菌材料生物相容性差、无荧光标记能力、细菌耐药性差等问题,本研究利用高分子抗菌材料的优势,以1,4双-(3-氨丙基)哌嗪、7-N,N-二乙氨基-3-醛基香豆素、相对分子质量800聚乙二醇的二丁二酸酯(PB)、叔丁基异腈、苯甲醛为原料,通过便捷高效、原子经济的Ugi反应制得新型含有哌嗪结构的荧光标记抗菌性哌嗪聚合物:聚(1,4双-(3-氨丙基)哌嗪/PB/醛/叔丁基异腈)(PC).借助1H NMR、FTIR表征了PC结构,并对PC进行了生物学性能研究:采用滤纸片法和细菌生长曲线法考察PC对金黄色葡萄球菌和大肠杆菌的抑菌性能.以MTT法及AM-PI双染色法评价PC的细胞毒性,并利用激光共聚焦显微镜对PC进行了活细胞成像研究.结果表明,质量浓度为50 mg/mL PC对大肠杆菌(Escherichia coli)和金黄色葡萄球菌(Staphylococcus aureus)的生长均有明显抑制作用.质量浓度为100 μg/mL持续作用72 h的PC不会产生明显的细胞毒性;同时PC能够标记活细胞并具有良好的荧光性能.综上所述,利用Ugi反应合成的带香豆素与哌嗪结构的聚合物PC可作为一种既有荧光标记能力又具有抗菌性能、对人体无害的生物材料.关键词:抗菌性聚合物;抑菌性能;细胞毒性;活细胞成像中图分类号:O633.4 文献标志码:A 文章编号:1000-1565(2020)02-0151-10Preparation and biological evaluation of fluorescently labeled piperazine antibacterial polymerSUN Zhuxing,DENG Kuilin,LIU Na,ZHANG Huanyu,LIU Hongmei(Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of Ministry of Education,College of Chemistry and Environment Science,Hebei University,Baoding 071002,China)Abstract: Considering at poor biocompatibility,no fluorescent labeling,and bacterial resistance for the antibacterial material,combining the advantages of polymer antibacterial materials,1,4 bis-(3-aminopropyl)piperazine,7-N,N-diethylamino-3-aldehyde coumarin,Dibutyrate with a molecular weight of 800 polyethylene glycol(PB),tert-butyl isonitrile and benzaldehyde are used as raw materials to obtain a novel fluorescently labeled antibacterial polymer(PC)with unique structure through high efficiency and atomic economic multi-component reaction-Ugi reaction.The polymer has been characterized by 1H NMR and FTIR.the antibacterial activity of PC against Staphylococcus aureus and Escherichia coli was examined by filter paper method and bacterial growth curve method.Then the biocompatibility of PC was evaluated by MTT and AM-PI double staining method.Live cell imaging studies of PC were performed by laser confocal microscopy.- 收稿日期:2019-07-15 基金项目:河北省自然科学基金资助项目(B2015201158);河北省药物创制协同创新中心专项经费(1050-595170218) 第一作者:孙竹兴(1994—),女,云南宣威人,河北大学在读硕士研究生.E-mail:15733292985@163.com 通信作者:刘红梅(1978—),女,河北保定人,河北大学副研究员,主要从事细胞分子生物学研究.E-mail:wzdd_may@126.com第2期孙竹兴等:荧光标记哌嗪抗菌聚合物的制备及生物学评价The results showed that concentration of 50 mg/mL PC significantly inhibited the growth of E.coli and S.aureus;and PC with a concentration of 100 μg/mL did not produce significant cytotoxicity;live cell imaging shows that PC can label living cells and has good fluorescence performance.Therefore,PC can be used as a new type of antibacterial material that has the ability to fluorescently label,antibacterial properties and is harmless to the human body.This provides a new choice for the use of antibacterial materials in the biomedical field.

Key words: antibacterial polymer, antibacterial activity, cytotoxicity, live cell imaging

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