多功能磁性荧光纳米药载的合成、表征及应用
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摘要
随着材料科学、化学、生命科学、药学和医学等学科的迅速发展与有机融合,作为纳米科学技术中的一个分支——纳米药物载体在疾病诊断、预防和治疗中显示出广阔的应用前景,对医学的发展产生了重要的推动作用。本论文从研究饮食补充物活性成分和作用机理入手,以改性或不改性的壳聚糖为基质,合成了三种具有示踪、磁响应和生物靶向性的多功能纳米药载,分别用于运送肽类药物(胰岛素)、亲水性药物(阿霉素)和疏水性药物(喜树碱),主要从以下五个方面进行了创新性研究：
1.将胰脏细胞膜吸附到大孔球形硅胶上制备细胞膜固定相,并填充成稳定性好、可再生、具有生物活性的色谱柱,再通过前沿亲和色谱方法测得芒果苷(MF)在色谱柱上的解离常数(Kd)和活性结合位点数(Bt)。实验结果表明芒果苷在胰脏细胞膜上存在着丰富的结合位点,并与膜蛋白之间具有较强的亲和性。这就为确证芒果苷在胰岛素信号通路中发挥调控作用提供了有力的证据。
2.利用高效液相色谱与超滤相结合的方法系统地研究了绿茶提取物(GTE)活性组分与药物传送途中相关蛋白质之间的作用特点。结果表明,表被儿茶素被酸酯(EGCG)和表被儿茶素(EGC)不仅与血浆运输蛋白(白蛋白)有较高的结合率,而且与细胞膜蛋白之间也有较高的结合率。由此推测,这两种儿茶素是绿茶提取物中的主要活性组分,绿茶对糖尿病和癌症的抑制作用应该与绿茶儿茶素活性组分和运输蛋白以及细胞膜蛋白的高亲和性有关。
3.以壳聚糖为基质,利用不同的壳聚糖/量子点/磁纳米颗粒比例和不同的参数条件,将超顺磁氧化铁和碲化镉量子点直接凝聚成不同形貌的磁性荧光(CLM)杂合纳米水溶胶。其中球形的CLM杂合纳米胶拥有理想的平均粒径(<160nrn),和较高的胰岛素上载量(约为40.1mg/g)。研究了在胰岛素受体介导下MF、EGCG和ECG对正常人肝L02细胞摄入上载胰岛素的CLM杂合纳米胶的影响。研究表明MF, EGCG和ECG能够促进胰岛素与L02细胞的靶向结合,并且改善L02细胞对胰岛素的敏感性。这为以上三种组分的抗糖尿病活性提供了证据,同时也拓展了纳米药载的应用潜力。
4.利用原位组装的方法,开发了一种新型的以羧甲基壳聚糖(CMCH)为基质,并键合有叶酸的磁性荧光纳米颗粒(CFLMNPs)。室温下CFLMNPs具有强烈的超顺磁和光致发光性能,在模拟的生理环境中,CFLMNPs的粒径范围是170-190nm。研究了抗癌药物阿霉素(ADM)在CFLMNPs上的上载量和累积释放特性。利用激光扫描共聚焦显微成像(LSCM)观察药载与细胞的相互作用,发现CFLMNPs是通过叶酸受体介导的内吞机制进入癌细胞的。这些结果表明,多功能的CFLMNPs具有较高的药物上载率、低毒性、癌细胞特异性靶向和良好的细胞相容性,有望成为靶向药物传送和细胞成像的理想纳米药载。
5.以球形磁性荧光杂合纳米水溶胶为核心,利用原位组装的方法,开发了一种新型的键合有叶酸-四肽复合物的磁性荧光纳米药载(CLM-tetrapeptide-FA)。在模拟的生理环境下,该纳米药载的粒径约为150-190nm。为靶向和上载喜树碱(CPT)而设计的叶酸-四肽袋状结构有效地保护了CPT,改善了其抗癌特性,并降低了毒副作用；而且,CPT的上载量可以通过键合不同疏水性的四肽加以调整,这是一种兼备上载药物和保护药物的新的药载设计理念。药载在磁诱导和叶酸受体介导下实现了对肿瘤细胞的双重特异性靶向。从细胞毒性研究和血液相容性研究表明,这是一种毒性低、生物相容性高的纳米药载,有望成为一种高效的肿瘤靶向性药物载体。
With the rapid development and organic integration of materials science, chemistry, life sciences, pharmacy and medical science, as a branch of nanoscale science and technology, the nanometer drug carrier has exhibited extensive application prospects in diagnosis, prevention and treatment of disease, and plays an important role in the development of medicine. This paper started from studying the active ingredients and effect mechanism of diet supplements, and presented three kinds of synthesis approaches of multifunctional nanometer drug carriers with tracing and targeting properties using modified or raw chitosan as matrixes for peptides drug (insulin), hydrophilism drug (adriamycin), and hydrophobicity drug (camptothecin) delivery, respectively. The more detailed novelty of this research can be categorized as following:
1. The cell membrane stationary phase (CMSP) was prepared by immobilizing rat islet pancreas cell membrane on the surface of silica. The resulting CMSP was filled into chromatographic column with enzymatic activity, stability and reproducibility. The dissociation constant (Kd) and the amount of active binding sites (B,) for mangiferin (MF) on cell membrane were determined using frontal chromatography. The results suggested that mangiferin possessed strong affinity with membrane protein and abundant binding sites on cell membrane, which provided powerful evidence for regulatory function of mangiferin on insulin signaling pathway.
2. The interaction properties of active compounds in green tea extract (GTE) and involved proteins in the path of drugs delivery were studied systematically by high performance liquid chromatography-UV/DAD combined with ultrafiltration. The results showed that (-)-epigallocatechin gallate (EGCG) and (-)-epicatechin gallate (ECG) were main active components in GTE. There were high binding degrees between two catechins and transportation proteins in plasma, and proteins on cell membrane. We suggest that the inhibition of the pathogenesis of some diseases (diabetes mellitus and cancer) by green tea should be associated with the high affinities of catechins to transportation proteins and cell membrane proteins.
3. The chitosan-based luminescent/magnetic (CLM) hybrid nanogels were synthesized with different chitosan/QD/MNP ratios and under different processing parameters by direct gelation of chitosan, CdTe and superparamagnetic iron oxide into the copolymer. Spherical CLM hybrid nanogels possessed appropriate average sizes (＜160nm) and moderate loading amount of insulin (40.1mg/g). Human normal hepatocytes L02cell line was used to explore the effects of additives, such as MF, EGCG, and ECG on the insulin-receptor-mediated cellular uptake using insulin-loaded CLM hybrid nanogels. The study demonstrates that MF, EGCG and ECG are potentially able to enhance targeting combination of insulin with L02cells and improve insulin sensitivity in L02cells, which provide directly evidence for antidiabetic activity of above three components and expand the potential application for the nano drug carrier.
4. A novel folate conjugated carboxymethyl chitosan-ferroferric oxide doped cadmium telluride quantum dot nanoparticles (abbreviate:CFLMNPs) was developed by assembly in situ. The as-prepared CFLMNPs possessed intense superparamagnetic and fluorescent property at room temperature. The size range of CFLMNPs was about170-190nm. The loading efficiency and cumulative release of anticancer drug (adriamycin, ADM) on the CFLMNPs were determined. The CFLMNPs were transported into the HepG2cells by an folate-receptor-mediated endocytosis mechanism. The results indicate that the multifunctional CFLMNPs possess a high drug loading efficiency, low cytotoxicity and favourable cell compatibility, and are promising candidates for carboxymethyl chitosan-based targeted drug delivery and cellular imaging.
5. A novel chitosan-based luminescent/magnetic hybrid nanoparticles with folate-conjugated tetrapeptide composites (CLMNPs-tetrapeptide-FA) was synthesized by direct gelation combined with conjugation in situ. The size range of CLMNPs-tetrapeptide-FA copolymers was approximately150-190nm. The folate-tetrapeptide pocket-like structures designed specifically for targeting and loading camptothecin (CPT) could prevent CPT from hydrolyzation and toxicity diffusion to some extent. Additionally, the loading amount of CPT could be regulated by conjugating different hydrophobic peptide on copolymer, which is a kind of new concept having both drug loading and drug protecting. Dual specific targeting of the copolymers to cancer cells was achieved under external magnetic field guidance combined with a folate-receptor-mediated endocytosis. The multifunctional CLMNPs-tetrapeptide-FA copolymers are promising candidates for tumor-targeted drug delivery.
1.将胰脏细胞膜吸附到大孔球形硅胶上制备细胞膜固定相,并填充成稳定性好、可再生、具有生物活性的色谱柱,再通过前沿亲和色谱方法测得芒果苷(MF)在色谱柱上的解离常数(Kd)和活性结合位点数(Bt)。实验结果表明芒果苷在胰脏细胞膜上存在着丰富的结合位点,并与膜蛋白之间具有较强的亲和性。这就为确证芒果苷在胰岛素信号通路中发挥调控作用提供了有力的证据。
2.利用高效液相色谱与超滤相结合的方法系统地研究了绿茶提取物(GTE)活性组分与药物传送途中相关蛋白质之间的作用特点。结果表明,表被儿茶素被酸酯(EGCG)和表被儿茶素(EGC)不仅与血浆运输蛋白(白蛋白)有较高的结合率,而且与细胞膜蛋白之间也有较高的结合率。由此推测,这两种儿茶素是绿茶提取物中的主要活性组分,绿茶对糖尿病和癌症的抑制作用应该与绿茶儿茶素活性组分和运输蛋白以及细胞膜蛋白的高亲和性有关。
3.以壳聚糖为基质,利用不同的壳聚糖/量子点/磁纳米颗粒比例和不同的参数条件,将超顺磁氧化铁和碲化镉量子点直接凝聚成不同形貌的磁性荧光(CLM)杂合纳米水溶胶。其中球形的CLM杂合纳米胶拥有理想的平均粒径(<160nrn),和较高的胰岛素上载量(约为40.1mg/g)。研究了在胰岛素受体介导下MF、EGCG和ECG对正常人肝L02细胞摄入上载胰岛素的CLM杂合纳米胶的影响。研究表明MF, EGCG和ECG能够促进胰岛素与L02细胞的靶向结合,并且改善L02细胞对胰岛素的敏感性。这为以上三种组分的抗糖尿病活性提供了证据,同时也拓展了纳米药载的应用潜力。
4.利用原位组装的方法,开发了一种新型的以羧甲基壳聚糖(CMCH)为基质,并键合有叶酸的磁性荧光纳米颗粒(CFLMNPs)。室温下CFLMNPs具有强烈的超顺磁和光致发光性能,在模拟的生理环境中,CFLMNPs的粒径范围是170-190nm。研究了抗癌药物阿霉素(ADM)在CFLMNPs上的上载量和累积释放特性。利用激光扫描共聚焦显微成像(LSCM)观察药载与细胞的相互作用,发现CFLMNPs是通过叶酸受体介导的内吞机制进入癌细胞的。这些结果表明,多功能的CFLMNPs具有较高的药物上载率、低毒性、癌细胞特异性靶向和良好的细胞相容性,有望成为靶向药物传送和细胞成像的理想纳米药载。
5.以球形磁性荧光杂合纳米水溶胶为核心,利用原位组装的方法,开发了一种新型的键合有叶酸-四肽复合物的磁性荧光纳米药载(CLM-tetrapeptide-FA)。在模拟的生理环境下,该纳米药载的粒径约为150-190nm。为靶向和上载喜树碱(CPT)而设计的叶酸-四肽袋状结构有效地保护了CPT,改善了其抗癌特性,并降低了毒副作用；而且,CPT的上载量可以通过键合不同疏水性的四肽加以调整,这是一种兼备上载药物和保护药物的新的药载设计理念。药载在磁诱导和叶酸受体介导下实现了对肿瘤细胞的双重特异性靶向。从细胞毒性研究和血液相容性研究表明,这是一种毒性低、生物相容性高的纳米药载,有望成为一种高效的肿瘤靶向性药物载体。
With the rapid development and organic integration of materials science, chemistry, life sciences, pharmacy and medical science, as a branch of nanoscale science and technology, the nanometer drug carrier has exhibited extensive application prospects in diagnosis, prevention and treatment of disease, and plays an important role in the development of medicine. This paper started from studying the active ingredients and effect mechanism of diet supplements, and presented three kinds of synthesis approaches of multifunctional nanometer drug carriers with tracing and targeting properties using modified or raw chitosan as matrixes for peptides drug (insulin), hydrophilism drug (adriamycin), and hydrophobicity drug (camptothecin) delivery, respectively. The more detailed novelty of this research can be categorized as following:
1. The cell membrane stationary phase (CMSP) was prepared by immobilizing rat islet pancreas cell membrane on the surface of silica. The resulting CMSP was filled into chromatographic column with enzymatic activity, stability and reproducibility. The dissociation constant (Kd) and the amount of active binding sites (B,) for mangiferin (MF) on cell membrane were determined using frontal chromatography. The results suggested that mangiferin possessed strong affinity with membrane protein and abundant binding sites on cell membrane, which provided powerful evidence for regulatory function of mangiferin on insulin signaling pathway.
2. The interaction properties of active compounds in green tea extract (GTE) and involved proteins in the path of drugs delivery were studied systematically by high performance liquid chromatography-UV/DAD combined with ultrafiltration. The results showed that (-)-epigallocatechin gallate (EGCG) and (-)-epicatechin gallate (ECG) were main active components in GTE. There were high binding degrees between two catechins and transportation proteins in plasma, and proteins on cell membrane. We suggest that the inhibition of the pathogenesis of some diseases (diabetes mellitus and cancer) by green tea should be associated with the high affinities of catechins to transportation proteins and cell membrane proteins.
3. The chitosan-based luminescent/magnetic (CLM) hybrid nanogels were synthesized with different chitosan/QD/MNP ratios and under different processing parameters by direct gelation of chitosan, CdTe and superparamagnetic iron oxide into the copolymer. Spherical CLM hybrid nanogels possessed appropriate average sizes (＜160nm) and moderate loading amount of insulin (40.1mg/g). Human normal hepatocytes L02cell line was used to explore the effects of additives, such as MF, EGCG, and ECG on the insulin-receptor-mediated cellular uptake using insulin-loaded CLM hybrid nanogels. The study demonstrates that MF, EGCG and ECG are potentially able to enhance targeting combination of insulin with L02cells and improve insulin sensitivity in L02cells, which provide directly evidence for antidiabetic activity of above three components and expand the potential application for the nano drug carrier.
4. A novel folate conjugated carboxymethyl chitosan-ferroferric oxide doped cadmium telluride quantum dot nanoparticles (abbreviate:CFLMNPs) was developed by assembly in situ. The as-prepared CFLMNPs possessed intense superparamagnetic and fluorescent property at room temperature. The size range of CFLMNPs was about170-190nm. The loading efficiency and cumulative release of anticancer drug (adriamycin, ADM) on the CFLMNPs were determined. The CFLMNPs were transported into the HepG2cells by an folate-receptor-mediated endocytosis mechanism. The results indicate that the multifunctional CFLMNPs possess a high drug loading efficiency, low cytotoxicity and favourable cell compatibility, and are promising candidates for carboxymethyl chitosan-based targeted drug delivery and cellular imaging.
5. A novel chitosan-based luminescent/magnetic hybrid nanoparticles with folate-conjugated tetrapeptide composites (CLMNPs-tetrapeptide-FA) was synthesized by direct gelation combined with conjugation in situ. The size range of CLMNPs-tetrapeptide-FA copolymers was approximately150-190nm. The folate-tetrapeptide pocket-like structures designed specifically for targeting and loading camptothecin (CPT) could prevent CPT from hydrolyzation and toxicity diffusion to some extent. Additionally, the loading amount of CPT could be regulated by conjugating different hydrophobic peptide on copolymer, which is a kind of new concept having both drug loading and drug protecting. Dual specific targeting of the copolymers to cancer cells was achieved under external magnetic field guidance combined with a folate-receptor-mediated endocytosis. The multifunctional CLMNPs-tetrapeptide-FA copolymers are promising candidates for tumor-targeted drug delivery.
引文
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