修饰环糊精的分子组装及其生物活性研究
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摘要
超分子化学是一门处于当代化学、材料化学和生命科学交汇点的新兴学科,主要研究对象是分子间的非共价相互作用。其中环糊精作为第二代主体化合物,其衍生物的分子识别与组装是超分子化学的一个重要研究方向。为了更好地揭示环糊精在分子识别原理下形成多功能组装体的性质,我们设计并合成了叶酸修饰β-环糊精和β-环糊精修饰透明质酸,并在此基础之上根据超分子相互作用原理构筑了超分子靶向药物传递体系,并且进一步评价了它们在体内和体外的抗肿瘤活性；除此之外,我们还合成了具有光致变色活性的桥联全甲基化β-环糊精,并研究了其与卟啉类化合物形成的组装体的光物理和光化学行为。具体研究内容如下：
1.简要介绍了超分子化学的概况,并简要归纳了近几年来环糊精在分子识别和分子自组装方面所取得的代表性成果和研究进展,继而进一步评述了基于超分子相互作用的靶向药物传递体系的最新研究成果。
2.通过金刚烷修饰的卟啉以非共价方式连接了叶酸修饰环糊精和石墨烯氧化物,并通过π-π相互作用将抗癌药物阿霉素负载到其表面,构筑了一种超分子靶向药物传递体系。生物实验结果表明在生理条件下该组装体以对正常细胞低毒性的方式将阿霉素有效地传递到肿瘤细胞和组织。
3.我们成功地构筑了一系列基于透明质酸和环糊精的共轭聚多糖化合物。该化合物通过主客体相互作用与金刚烷顺铂前药进行非共价结合,得到了一种具有能够特异性地识别癌细胞的亲水性HA外壳以及疏水性药物内核的纳米超分子靶向抗癌药物传递体系。生物实验结果表明,我们制备的这种纳米粒子表现出了与商品化抗癌药物顺铂相似的抗癌活性以及更低的毒副作用。
4.合成了一种新颖的二芳基乙烯桥联的全甲基化β-环糊精,通过全甲基化β-环糊精与卟啉间强的超分子相互作用构筑了一种线状纳米组装体。该组装体可以通过紫外／可见光的照射,来控制主体与客体间的FRET过程,进而调控卟啉分子荧光的淬灭与恢复。
Supramolecular chemistry, which is focus on the non-covalent interaction between molecules, is a type of interdiscipline composed of modern chemistry, material chemistry and life science. As the second generation of host compounds, the molecular recognition and assembly of cyclodextrin (CD) is the most important part in supramolecular chemistry. In this thesis, we constructed two types of supramolecular targeted anticancer drug delivery systems based on synthesized folic acid (FA) modified β-CD and/β-CD modified hyaluronic acid, respectively, and then we further valuated their antitumor activities in vitro and in vivo. In addition, we synthesized a novel bridged bis(permethyl-β-cyclodextrin)s with photochromic properties, and then investigated the photophysics and photochemistry properties of the assembly formed with porphyrin. The content of the thesis is as follows:
1. Besides the introduction of supramolecular chemistry, we concluded the research progress in molecular recognition and assembly of cyclodextrin, and then generally commented the newest research achievements in design of targeted drug delivery systems based on supramolecular interactions.
2. We constructed a nanosupramolecular assembly by FA-modified β-CD and GO noncovalently linked by adamantane-grafted porphyrin. The resulting quarternary supramolecular nanoarchitecture based on strong π-π stacking between the porphyrin and GO and the high hydrophobic affinity between β-CD and adamantane, can be employed as a targeted delivery system to efficiently carry doxorubicin to tumor tissues with low toxicity to normal cells under physiological conditions.
3. A series of conjugated polysaccharide nanoparticle, named hyaluronic acid particle (HAP), composed of a hydrophobic anticancer drug core and a hydrophilic HA shell was successfully constructed by host-guest interaction between β-CD-modified HA and adamplatin prodrug. The resultant nanometer-sized HAP could recognize HA receptors over-expressed cancer cells. Biological experiments demonstrated that HAP exhibited similar anticancer activities to, and lower side effects than commercial anticancer drug cisplatin in vitro and in vivo.
4. We synthesized a novel dithienylethene-bridged bis(permethyl-β-cyclodextrin)s. Taking advantage of the high affinity between host compound and porphyrin derivant, we conveniently constructed a linear supramolecular architecture and carefully studied the light-controlled fluorescence resonance energy transfer process through host-guest interaction by means of fluorescent spectrometry.
1.简要介绍了超分子化学的概况,并简要归纳了近几年来环糊精在分子识别和分子自组装方面所取得的代表性成果和研究进展,继而进一步评述了基于超分子相互作用的靶向药物传递体系的最新研究成果。
2.通过金刚烷修饰的卟啉以非共价方式连接了叶酸修饰环糊精和石墨烯氧化物,并通过π-π相互作用将抗癌药物阿霉素负载到其表面,构筑了一种超分子靶向药物传递体系。生物实验结果表明在生理条件下该组装体以对正常细胞低毒性的方式将阿霉素有效地传递到肿瘤细胞和组织。
3.我们成功地构筑了一系列基于透明质酸和环糊精的共轭聚多糖化合物。该化合物通过主客体相互作用与金刚烷顺铂前药进行非共价结合,得到了一种具有能够特异性地识别癌细胞的亲水性HA外壳以及疏水性药物内核的纳米超分子靶向抗癌药物传递体系。生物实验结果表明,我们制备的这种纳米粒子表现出了与商品化抗癌药物顺铂相似的抗癌活性以及更低的毒副作用。
4.合成了一种新颖的二芳基乙烯桥联的全甲基化β-环糊精,通过全甲基化β-环糊精与卟啉间强的超分子相互作用构筑了一种线状纳米组装体。该组装体可以通过紫外／可见光的照射,来控制主体与客体间的FRET过程,进而调控卟啉分子荧光的淬灭与恢复。
Supramolecular chemistry, which is focus on the non-covalent interaction between molecules, is a type of interdiscipline composed of modern chemistry, material chemistry and life science. As the second generation of host compounds, the molecular recognition and assembly of cyclodextrin (CD) is the most important part in supramolecular chemistry. In this thesis, we constructed two types of supramolecular targeted anticancer drug delivery systems based on synthesized folic acid (FA) modified β-CD and/β-CD modified hyaluronic acid, respectively, and then we further valuated their antitumor activities in vitro and in vivo. In addition, we synthesized a novel bridged bis(permethyl-β-cyclodextrin)s with photochromic properties, and then investigated the photophysics and photochemistry properties of the assembly formed with porphyrin. The content of the thesis is as follows:
1. Besides the introduction of supramolecular chemistry, we concluded the research progress in molecular recognition and assembly of cyclodextrin, and then generally commented the newest research achievements in design of targeted drug delivery systems based on supramolecular interactions.
2. We constructed a nanosupramolecular assembly by FA-modified β-CD and GO noncovalently linked by adamantane-grafted porphyrin. The resulting quarternary supramolecular nanoarchitecture based on strong π-π stacking between the porphyrin and GO and the high hydrophobic affinity between β-CD and adamantane, can be employed as a targeted delivery system to efficiently carry doxorubicin to tumor tissues with low toxicity to normal cells under physiological conditions.
3. A series of conjugated polysaccharide nanoparticle, named hyaluronic acid particle (HAP), composed of a hydrophobic anticancer drug core and a hydrophilic HA shell was successfully constructed by host-guest interaction between β-CD-modified HA and adamplatin prodrug. The resultant nanometer-sized HAP could recognize HA receptors over-expressed cancer cells. Biological experiments demonstrated that HAP exhibited similar anticancer activities to, and lower side effects than commercial anticancer drug cisplatin in vitro and in vivo.
4. We synthesized a novel dithienylethene-bridged bis(permethyl-β-cyclodextrin)s. Taking advantage of the high affinity between host compound and porphyrin derivant, we conveniently constructed a linear supramolecular architecture and carefully studied the light-controlled fluorescence resonance energy transfer process through host-guest interaction by means of fluorescent spectrometry.
引文
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