聚丙烯酸修饰壳聚糖纳米球锌卟啉结合体的制备与性能研究
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摘要
壳聚糖是一种性能优良的生物高分子,具有良好的稳定性、水溶性和带正电性,这些特点使其在液态介质中可与带负电荷的聚合物、大分子甚至一些聚阴离子相互作用。壳聚糖是一类重要的药物控释载体材料,因其特别适用于多肽、蛋白质、核酸、疫苗等生物活性大分子药物的包埋和释放而受到关注。化学修饰后的壳聚糖纳米球仍能保持良好的生物相容性、低毒性和稳定性。聚丙烯酸修饰壳聚糖纳米球也是近年来制备很多的一种纳米材料,在很多方面有所应用。本论文首次将水不溶性金属卟啉锌配合物与聚丙烯酸修饰壳聚糖纳米球结合,制得一种新型的结合有功能化合物的水溶性天然高分子纳米球,以期拓宽壳聚糖和金属卟啉的应用领域。
论文首先对多糖基纳米球的主要种类和用途进行了综述,并介绍了目前壳聚糖基纳米球的制备方法及其在负载各类药物方面的应用情况,总结了各种方法存在的问题。
其次,用原位聚合的方法制备了聚丙烯酸修饰壳聚糖纳米球(CS-GA-PAA-NPs),将其与中位-四取代基苯基卟啉锌结合制备了四种聚丙烯酸修饰壳聚糖纳米球锌卟啉结合体( ZnTpMoPP/CS-GA-PAA-NPs、ZnTpHPP/CS-GA-PAA-NPs、ZnToHPP/CS-GA-PAA-NPs和ZnTmMpHPP/CS -GA-PAA-NPs),通过紫外-可见光谱、动态光散射等对其进行了表征,结果表明:CS-GA-PAA-NPs与卟啉锌配合物结合后体系稳定、粒径均一;推测卟啉锌与CS-GA-PAA-NPs以配位键结合;且CS-GA-PAA-NPs对卟啉锌的分散非常好,是有机溶剂与水的混合溶剂对卟啉锌分散程度的6~26倍。
第三,论文从两个方面探索了聚丙烯酸修饰壳聚糖纳米球锌卟啉结合体的功能。(1)聚对氧自由基的清除:中位-四苯基金属卟啉及其衍生物的合成及分离较为简单,在氧自由基清除方面具有广阔的应用前景。由于人体内自由基处在亲水性环境中,因此提高金属卟啉作为氧自由基清除酶模型物的亲水性是目前需解决的最主要问题。本文研究了四种聚丙烯酸修饰壳聚糖纳米球锌卟啉结合体对O2.-的清除,发现其去除O2.-活性良好,EC50值在1.99μmol/L~ 8.60μmol/L之间,对天然SOD酶的模拟度最高可达3.02% ,其活性顺序为ZnTpMoPP/CS-GA-PAA-NPs > ZnTmMpHPP/CS-GA-PAA-NPs > ZnToHPP/CS-GA-PAA-NPs>ZnTpHPP/CS-GA-PAA-NPs。(2)在光电子转移反应中的光敏性。以ZnTpHPP/CS-GA-PAA-NPs为代表,研究了聚丙烯酸修饰壳聚糖纳米球锌卟啉结合体的光敏性,发现甲基紫精(MV2+)对ZnTpHPP/CS-GA-PAA-NPs的荧光有猝灭作用;在以TEOA为还原剂,ZnTpHPP/CS-GA-PAA-NPs为光敏剂的TEOA/[ZnTpHPP/CS-GA-PAA-NPs]/[MV2+]体系中,发现ZnTpHPP/CS-GA-PAA -NPs可将光电子转移到MV2+ ,使其变成激发态,表明ZnTpHPP/ CS-GA-PAA-NPs是一种良好的天然高分子光敏剂,并对其产氢功能进行了探索。
总之,所制备的聚丙烯酸修饰壳聚糖纳米球锌卟啉结合体具有清除自由基性能和光敏性,研究结果拓宽了壳聚糖与金属卟啉的应用范围,对开发新型高分子抗氧化剂、高分子电子转移反应体系及新型能源有潜在应用前景。
Chitosan has good stability, water-solubility and positive electrical property, which is an excellent biological macromolecule. Because of its particularly suitable for embedding and releasing peptides, proteins, nucleic acids, vaccines and other bioactive molecules, chitosan was concerned by researchers in recent years. In this paper, in order to expand the application range of chitosan and metalloporphyrins, a new type of water-soluble, functional and natural polymer nanoparticles was prepared by the way of coordinate bonding. It was insoluble metalloporphyrins combined with chitosan/ poly (acrylic acid) nanoparticles.
First of all, main types of polysaccharide nanoparticles, the preparation methods and applications of chitosan nanoparticles were reviewed.
Secondly, the chitosan/ polyacrylic acid nanoparticles (CS-PAA-NPs) were prepared by in-situ polymerization. Then the glutaraldehyde crosslinked chitosan/polyacrylic acid nanoparticles (CS-GA-PAA-NPs) were obtained via glutaraldehyde cross-linking. Four kinds of chitosan/ polyacrylic acid nanoparticles binding porphinatozinc were prepared by the way of complexing different zinc porphyrins with CS-GA-PAA-NPs. And they were characterized by UV-Vis spectra and DLS, which were named as ZnTpMoPP/CS-GA-PAA-NPs, ZnTpHPP/CS-GA -PAA-NPs, ZnToHPP/CS-GA-PAA-NPs and ZnTmMpHPP/CS-GA-PAA-NPs. It was concluded that the system was stable and the size of nanoparticles was uniform. It was conjectured that porphyrinatozinc and CS-GA-PAA-NPs was complexed by coordinate bonding. It was shown that porphyrinatozinc was better dispersed by CS/ PAA nanoparticles than by the solution of mixed organic solvent and water.
Thirdly, in this thesis, the functions of CS-GA-PAA-NPs binding porphinatozinc were explored from two aspects, respectively.
1) The oxygen free radical scavenging property of CS-GA-PAA-NPs binding porphinatozinc. The synthesis and separation of meso-tetraphenylporphyrins and their derivatives were relatively simple. So they have a broad application in the oxygen free radical scavenging. Metalloporphyrins can be used as enzyme model compound to eliminate oxygen free radicals. To improve metalloporphyrins’hydrophilicity is the main problem need to be solved because free radicals of human body were in a hydrophilic environment. In this paper, the superoxide anion radical scavenging property of CS-GA-PAA-NPs binding porphinatozinc was investigated. CS-GA-PAA-NPs binding porphinatozinc showed excellent scavenging activity compared with the properties of CS-GA-PAA-NPs and porphinatozinc complexes. The EC50 values of CS-GA-PAA-NPs binding porphinatozinc were between 1.99μmol/L and 8.60μmol/L. The degree to simulate the natural SOD enzyme of CS-GA-PAA-NPs binding porphinatozinc was up to 3.02%. The order of scavenging activity of four kinds of CS-GA-PAA-NPs binding porphinatozinc was ZnTpMoPP / CS-GA-PAA-NPs > ZnTmMpHPP/CS-GA-PAA-NPs > ZnToHPP/CS-GA-PAA -NPs > ZnTpHPP/CS-GA-PAA-NPs.
2) The photosensitivity of CS-GA-PAA-NPs binding porphinatozinc. In this thesis, the photosensitivity of ZnTpHPP/CS-GA-PAA-NPs was also investigated. The Fluorescence of ZnTpHPP/CS-GA-PAA-NPs can be quenched by methyl viologen (MV2+). The photoinduced electron transfer reaction from ZnTpHPP/CS-GA-PAA-NPs to the water-soluble cationic acceptor (MV2+) in [ZnTpHPP/CS-GA-PAA-NPs] / MV2+/ TEOA system was also studied with durative irradiated illumination. It was shown that ZnTpHPP/CS-GA-PAA-NPs was a good natural polymer photosensitizer. The function of hydrogen production was also explored.
In a word, CS-GA-PAA-NPs binding porphinatozinc have good property of scavenging oxygen free radicals and photosensitivity. The application of chitosan and metalloporphyrin has been enhanced, which can provide potential application prospect to develop new polymer antioxiunts, polymer electronic transfer reaction system and new energy.
论文首先对多糖基纳米球的主要种类和用途进行了综述,并介绍了目前壳聚糖基纳米球的制备方法及其在负载各类药物方面的应用情况,总结了各种方法存在的问题。
其次,用原位聚合的方法制备了聚丙烯酸修饰壳聚糖纳米球(CS-GA-PAA-NPs),将其与中位-四取代基苯基卟啉锌结合制备了四种聚丙烯酸修饰壳聚糖纳米球锌卟啉结合体( ZnTpMoPP/CS-GA-PAA-NPs、ZnTpHPP/CS-GA-PAA-NPs、ZnToHPP/CS-GA-PAA-NPs和ZnTmMpHPP/CS -GA-PAA-NPs),通过紫外-可见光谱、动态光散射等对其进行了表征,结果表明:CS-GA-PAA-NPs与卟啉锌配合物结合后体系稳定、粒径均一;推测卟啉锌与CS-GA-PAA-NPs以配位键结合;且CS-GA-PAA-NPs对卟啉锌的分散非常好,是有机溶剂与水的混合溶剂对卟啉锌分散程度的6~26倍。
第三,论文从两个方面探索了聚丙烯酸修饰壳聚糖纳米球锌卟啉结合体的功能。(1)聚对氧自由基的清除:中位-四苯基金属卟啉及其衍生物的合成及分离较为简单,在氧自由基清除方面具有广阔的应用前景。由于人体内自由基处在亲水性环境中,因此提高金属卟啉作为氧自由基清除酶模型物的亲水性是目前需解决的最主要问题。本文研究了四种聚丙烯酸修饰壳聚糖纳米球锌卟啉结合体对O2.-的清除,发现其去除O2.-活性良好,EC50值在1.99μmol/L~ 8.60μmol/L之间,对天然SOD酶的模拟度最高可达3.02% ,其活性顺序为ZnTpMoPP/CS-GA-PAA-NPs > ZnTmMpHPP/CS-GA-PAA-NPs > ZnToHPP/CS-GA-PAA-NPs>ZnTpHPP/CS-GA-PAA-NPs。(2)在光电子转移反应中的光敏性。以ZnTpHPP/CS-GA-PAA-NPs为代表,研究了聚丙烯酸修饰壳聚糖纳米球锌卟啉结合体的光敏性,发现甲基紫精(MV2+)对ZnTpHPP/CS-GA-PAA-NPs的荧光有猝灭作用;在以TEOA为还原剂,ZnTpHPP/CS-GA-PAA-NPs为光敏剂的TEOA/[ZnTpHPP/CS-GA-PAA-NPs]/[MV2+]体系中,发现ZnTpHPP/CS-GA-PAA -NPs可将光电子转移到MV2+ ,使其变成激发态,表明ZnTpHPP/ CS-GA-PAA-NPs是一种良好的天然高分子光敏剂,并对其产氢功能进行了探索。
总之,所制备的聚丙烯酸修饰壳聚糖纳米球锌卟啉结合体具有清除自由基性能和光敏性,研究结果拓宽了壳聚糖与金属卟啉的应用范围,对开发新型高分子抗氧化剂、高分子电子转移反应体系及新型能源有潜在应用前景。
Chitosan has good stability, water-solubility and positive electrical property, which is an excellent biological macromolecule. Because of its particularly suitable for embedding and releasing peptides, proteins, nucleic acids, vaccines and other bioactive molecules, chitosan was concerned by researchers in recent years. In this paper, in order to expand the application range of chitosan and metalloporphyrins, a new type of water-soluble, functional and natural polymer nanoparticles was prepared by the way of coordinate bonding. It was insoluble metalloporphyrins combined with chitosan/ poly (acrylic acid) nanoparticles.
First of all, main types of polysaccharide nanoparticles, the preparation methods and applications of chitosan nanoparticles were reviewed.
Secondly, the chitosan/ polyacrylic acid nanoparticles (CS-PAA-NPs) were prepared by in-situ polymerization. Then the glutaraldehyde crosslinked chitosan/polyacrylic acid nanoparticles (CS-GA-PAA-NPs) were obtained via glutaraldehyde cross-linking. Four kinds of chitosan/ polyacrylic acid nanoparticles binding porphinatozinc were prepared by the way of complexing different zinc porphyrins with CS-GA-PAA-NPs. And they were characterized by UV-Vis spectra and DLS, which were named as ZnTpMoPP/CS-GA-PAA-NPs, ZnTpHPP/CS-GA -PAA-NPs, ZnToHPP/CS-GA-PAA-NPs and ZnTmMpHPP/CS-GA-PAA-NPs. It was concluded that the system was stable and the size of nanoparticles was uniform. It was conjectured that porphyrinatozinc and CS-GA-PAA-NPs was complexed by coordinate bonding. It was shown that porphyrinatozinc was better dispersed by CS/ PAA nanoparticles than by the solution of mixed organic solvent and water.
Thirdly, in this thesis, the functions of CS-GA-PAA-NPs binding porphinatozinc were explored from two aspects, respectively.
1) The oxygen free radical scavenging property of CS-GA-PAA-NPs binding porphinatozinc. The synthesis and separation of meso-tetraphenylporphyrins and their derivatives were relatively simple. So they have a broad application in the oxygen free radical scavenging. Metalloporphyrins can be used as enzyme model compound to eliminate oxygen free radicals. To improve metalloporphyrins’hydrophilicity is the main problem need to be solved because free radicals of human body were in a hydrophilic environment. In this paper, the superoxide anion radical scavenging property of CS-GA-PAA-NPs binding porphinatozinc was investigated. CS-GA-PAA-NPs binding porphinatozinc showed excellent scavenging activity compared with the properties of CS-GA-PAA-NPs and porphinatozinc complexes. The EC50 values of CS-GA-PAA-NPs binding porphinatozinc were between 1.99μmol/L and 8.60μmol/L. The degree to simulate the natural SOD enzyme of CS-GA-PAA-NPs binding porphinatozinc was up to 3.02%. The order of scavenging activity of four kinds of CS-GA-PAA-NPs binding porphinatozinc was ZnTpMoPP / CS-GA-PAA-NPs > ZnTmMpHPP/CS-GA-PAA-NPs > ZnToHPP/CS-GA-PAA -NPs > ZnTpHPP/CS-GA-PAA-NPs.
2) The photosensitivity of CS-GA-PAA-NPs binding porphinatozinc. In this thesis, the photosensitivity of ZnTpHPP/CS-GA-PAA-NPs was also investigated. The Fluorescence of ZnTpHPP/CS-GA-PAA-NPs can be quenched by methyl viologen (MV2+). The photoinduced electron transfer reaction from ZnTpHPP/CS-GA-PAA-NPs to the water-soluble cationic acceptor (MV2+) in [ZnTpHPP/CS-GA-PAA-NPs] / MV2+/ TEOA system was also studied with durative irradiated illumination. It was shown that ZnTpHPP/CS-GA-PAA-NPs was a good natural polymer photosensitizer. The function of hydrogen production was also explored.
In a word, CS-GA-PAA-NPs binding porphinatozinc have good property of scavenging oxygen free radicals and photosensitivity. The application of chitosan and metalloporphyrin has been enhanced, which can provide potential application prospect to develop new polymer antioxiunts, polymer electronic transfer reaction system and new energy.
引文
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