龙脑手性与界面抗菌性能关系

发布时间：2018-04-26 03:32

本文选题：龙脑 + 聚丙烯酸龙脑酯　；参考：《北京化工大学》2015年硕士论文

【摘要】：细菌等微生物在材料表面粘附并繁殖生长会形成生物膜,生物膜的形成会造成疾病感染、环境污染等一系列问题。近年来,生物膜对人类造成的影响与危害越来越严重。因此,正确认识材料表面与细菌之间的相互作用关系,防止细菌生物膜的形成是全球关注的重要课题,也是目前科学研究的前沿和热点。现有的抗菌材料主要通过固定或释放杀菌物质实现抗菌,有一定的局限性,新型高效的抗菌材料及抗菌策略是目前研究者关注的重点。在抗菌研究领域,利用材料表面分子手性实现抗菌的研究还较少。因此,对聚合物的表面手性立体化学结构与材料表面抗菌性能关系进行研究,对于开发新型抗菌高分子材料、优化材料抗菌性能具有重要的现实意义。龙脑作为一种天然手性药物分子,具有多种手性立体化学结构。本文以三种不同手性的龙脑分子为原料,通过酯化反应合成丙烯酸龙脑酯单体(BAs),进而通过聚合反应合成含手性龙脑的高分子聚合物—聚丙烯酸龙脑酯(PBAs),通过GC-MS、1H-NMR、GPC、CD及CA等一系列表征方法,证明目标产物合成成功。采用“越狱”实验、菌液共培养、光密度(OD)及平板计数法等方法测定该新型高分子材料的抗菌性能,同时对材料的细胞毒性、生物相容性等问题进行研究。进一步地,将丙烯酸异龙脑酯单体(IBA)和甲基丙烯酸甲酯坼体(MMA)按不同的比例混合,经聚合反应制备得到高分子共聚物,并研究它们的抗菌粘附性能。主要研究成果如下：1.本文成功合成了不同手性的PBAs新型高分子聚合物。2.PBAs聚合物材料具有广谱抗菌性,对大肠杆菌、金黄色葡萄球菌及毛霉菌具有较强的抑制粘附作用,抑菌时间可达5天。3.聚丙烯酸左龙脑酯(PLBA)与聚丙烯酸异龙脑酯(PIBA)比聚丙烯酸右龙脑酯(PDBA)显示出更好的抗菌活性。4.PBAs聚合物具有良好的稳定性、生物相容性、无毒性等特点,可作为抗菌材料用于包括医学、食品、卫生、及环保等领域,发展潜力巨大。5.对于共聚物材料体系,随着IBA单体含量的增加,共聚物材料的抗菌活性有所提高；其中IBA单体的添加量达到50%时,共聚物材料的抗菌性能接近PIBA的抗菌性能,对大肠杆菌、枯草芽孢杆菌具有较强的抑制粘附作用。因此,新型共聚物材料能改善聚甲基丙烯酸甲酯(PMMA)的抗菌性能,这对PMMA材料在临床医学等领域的抗菌应用具有重要意义。研究结果表明,龙脑基抗菌高分子材料的抗菌机理是：PBA拥有较为复杂的双环单萜结构,具有三个手性中心,其主要通过表面手性立体化学结构影响细菌识别材料表面过程,阻止细菌粘附。从生物的角度来看,细菌不倾向于粘附在具有此种立体化学结构的材料表面。这种立体化学抗粘机制具有普适性,是一种新的抗菌策略。
[Abstract]:Bacteria and other microorganisms adhere to the surface of the material and reproduce and grow to form biofilm. The formation of biofilm will cause a series of problems, such as disease infection, environmental pollution and so on. In recent years, biofilm has caused more and more serious harm to human beings. Therefore, the correct understanding of the interaction between the surface of materials and bacteria to prevent the formation of bacterial biofilm is an important issue of global concern, but also the frontier and hot spot of scientific research. The existing antimicrobial materials have some limitations by immobilization or release of bactericidal substances. New and efficient antibacterial materials and antimicrobial strategies are the focus of researchers. In the field of antimicrobial research, there is little research on using surface molecular chirality to realize antimicrobial activity. Therefore, the study of the relationship between the surface chiral stereochemical structure of polymers and the antibacterial properties of the materials has important practical significance for the development of new antimicrobial polymer materials and the optimization of the antibacterial properties of the materials. As a natural chiral drug molecule, borneol has many chiral stereochemical structures. In this paper, three kinds of chiral borneol molecules were used as raw materials. The borneol acrylate monomer (BAsN) was synthesized by esterification reaction, and then a high molecular polymer containing borneol acrylate (PBAsC) was synthesized by polymerization. The synthesis of the target product was proved successful by a series of characterization methods, such as GC-MSX 1H-NMRGPC-CD and CA. The antibacterial properties of the new polymer material were determined by means of "jailbreak" experiment, bacterial solution co-culture, optical density ODV and plate counting. The cytotoxicity and biocompatibility of the material were also studied. Furthermore, the isobornyl acrylate (IBA) and methyl methacrylate (MMA) were mixed in different proportions to prepare polymer copolymers, and their antibacterial and adhesion properties were studied. The main research results are as follows: 1. In this paper, we have successfully synthesized novel PBAs polymers with different chiral properties. 2. PBAs polymer materials have broad spectrum antibacterial properties, and have a strong inhibitory effect on Escherichia coli, Staphylococcus aureus and Mucor. The antibacterial time can be up to 5 days. 3. Poly (L-borneol) (PLBA) and polyisobornate (PIBA) showed better antimicrobial activity than PDBA. (4) PBAs polymer had good stability, biocompatibility, non-toxicity and so on. Can be used as antimicrobial materials, including medicine, food, hygiene, environmental protection and other fields, development potential is huge. For the copolymers, the antibacterial activity of the copolymers increased with the increase of the content of IBA monomers, and the antibacterial properties of the copolymers were close to those of PIBA when the amount of IBA monomer reached 50, and the antibacterial activity of the copolymers was similar to that of Escherichia coli. Bacillus subtilis has a strong inhibitory effect on adhesion. Therefore, the new copolymer material can improve the antimicrobial properties of PMMA, which is of great significance for the antibacterial application of PMMA materials in clinical medicine and other fields. The results showed that the antibacterial mechanism of borne-based antimicrobial polymer was that the Bicyclic monoterpene structure of WPBA was complex and had three chiral centers, which mainly affected the surface process of bacteria recognition materials by surface chiral stereochemical structure. Prevent bacterial adhesion. From a biological point of view, bacteria do not tend to adhere to the surface of materials with this stereochemical structure. This stereochemical anti-adhesion mechanism is universal and a new antimicrobial strategy.
【学位授予单位】：北京化工大学
【学位级别】：硕士
【学位授予年份】：2015
【分类号】：TB34

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