摘要
在生物醫學和材料科學領域，新型智能奈米材料的開發已有顯著的發展。在過去的幾十年中，開發了許多具有不同形狀、大小和結構的奈米材料，其中包括樹枝狀聚合物、聚合物奈米顆粒及超分子聚合物微胞作為藥物遞送系統。值得注意的是，最近在生物工程和奈米技術領域中，刺激響應性奈米材料受到了極大的關注。智能奈米材料因具有較高穩定性、標靶特性及生物利用度而具有巨大的潛力，且能夠有效克服疏水性藥物（如抗癌療法）所造成的負向影響，利用標靶特性來識別癌症組織並釋放其藥物。然而，由於有著藥物的過早釋放和非目標性釋放藥物的缺點，在眾多研究中的奈米載體只有極少數通過了臨床階段。為了克服這些挑戰，透過利用次級相互作用（如多重氫鍵、π-π堆積、主體-客體相互作用及離子相互作用力）來建構聚合物微胞，以改善其結構穩定性與靶向遞送效率。在本篇論文中，包含三種基於次級相互作用力所設計的不同智能型超分子奈米載體並評估其癌症治療的效果。
首先，我們開發了一種具高光敏性的尿嘧啶功能化超分子微胞，由於尿嘧啶的自互補性氫鍵相互作用和高載藥量，在水溶液中表現出穩定的自組裝行為。有趣的是，細胞攝取分析與膜聯蛋白V /碘化丙啶雙重染色實驗結果表明，膠束的光二聚化加速癌細胞吞噬的效果，從而導致癌細胞中有更高程度的細胞凋亡。因此，將光敏性尿嘧啶基團導入超分子微胞結構中是增進藥物安全性及癌症治療有效性的重要關鍵。
第二，透過腺嘌呤及尿嘧啶結合的官能化聚丙二醇而形成互補性氫鍵體系並具有溫度和光敏感的特性。這些互補體系可在水中自組裝成球形微胞，其微胞具有特異的兩親性、可調控的光誘導相變行為、優異的生物相容性及可控的形態及尺寸。除此之外，可以對藥物含量和包封效率進行調控，並可以透過溫度和光照射的變化來調節藥物釋放動力學，因此極具潛力應用於藥物傳遞及癌症治療。重要的是，經由細胞毒性和流式細胞儀分析證實，照光後的載藥微胞對癌細胞具有更強的細胞毒性作用，並且比原始的藥物和載藥微胞表現出更高的細胞吞噬效率，表明照光後的載藥微胞夠迅速進入腫瘤細胞內部，誘導大量細胞凋亡。因此，此新開發的超分子系統可作為安全及有效的奈米載體，有效抑制原發性腫瘤的生長和擴散。
第三，透過一種簡單且突破性的策略，將尿嘧啶官能化的聚丙二醇和二價汞離子結成來形成一種新型的金屬超分子聚合物。超分子聚合物的存在誘導複合體在水中自組裝成奈米尺寸的球形微胞。此外，汞離子配位到超分子聚合物結構中還提供其他特異的物理特性，例如在生物體環境中具有高度的結構穩定性、獨特的螢光特性、高靈敏的pH響應性來誘導汞離子釋放。有趣的是，細胞毒性和螢光影像結果證實，此新型微胞具有選擇性内吞作用進入癌細胞内部並毒殺細胞，並且不會影響正常細胞，這些優點使其微胞成為極具吸引力的抗癌奈米材料。除此之外，使用雙重染色的流式細胞儀研究結果證實，微胞表現出對於癌細胞具有快速且高比例的細胞凋亡，同時也因其選擇性內吞特性，可以使正常細胞不受影響。因此，本次研究成功證實此新方法能用於開發安全有效的金屬超分子奈米微胞並大幅增進癌症治療的效果。

Abstract
Development of new smart nanomaterials have been grown significantly in the field of biomedical and material sciences. In the past decades, several nanomaterials have been reported with different shape, size and architecture including dendrimers, polymeric nanoparticles, and polymeric micelles as drug delivery systems. More importantly, stimuli-responsive nanomaterials have received significant attentions in the field of bioengineering and nanotechnology recently. Smart nanomaterials due to their higher plasma stability, target specificity, and bioavailability, have great potential to overcome the adverse effect of hydrophobic drugs like anticancer therapeutics because they are capable of intelligently responding to the tumor microenvironment for target specific release of their drug payloads. However, only few of the numerous reported nanocarriers passed clinical stage due to the listed challenges, premature release and non-targeted delivery of their cargo. To address these challenges, many polymeric micelles have been developed based on secondary interactions such as, multiple hydrogen bonding, π-π stacking, host-guest interactions and ionic interactions to improve structural stability and targeted delivery efficiency. In this dissertation we have included three different intelligent supramolecular nanocarriers designed based on secondary interactions for effective treatment of cancer.
First, we developed a highly photosensitive uracil-functionalized supramolecular micelle which exhibits stable self-assembly behavior in aqueous solutions due to the self-complementary hydrogen bonding interactions between uracil moieties and high drug loading content. Interestingly, the cellular uptake analysis and the Annexin V/PI (propidium iodide) double staining assays demonstrated that the Photodimerization of micelles leads to an enhanced cellular internalization which consequently lead to higher degree of apoptosis in cancer cells. Thus, incorporation of photosensitive uracil groups into the supramolecular polymer structures could be an effective strategy to develop a nanocarriers that could enhance safety and efficacy of conventional hydrophobic drugs.
Second, Thermoresponsive and photosensitive complementary systems were developed by combining adenine (A) and uracil (U) functionalized polypropylene glycol. These complementary systems can self-assembled into spherical micelles with higher stability in aqueous environment. The resulting micelles possess unique amphiphilic properties, photo-induced tunable phase-transition behavior, excellent biocompatibility, well controlled spherical morphology, and can be tailored in size. Moreover, the drug content and entrapment efficiency can be finely tuned, and release kinetics can be modulated using combinations of changes in temperature and photoirradiation, making these micelles attractive drug nanocarriers. Importantly, cytotoxicity and flow cytometric analyses confirmed that drug-loaded irradiated micelles exerted more potent cytotoxic effects against cancer cells and exhibited much higher cellular uptake efficiency than the free drug and drug-loaded non-irradiated micelles, indicating that the drug-loaded irradiated micelles rapidly entered the tumor cells to induce massive cell death. Therefore, this newly-developed supramolecular system could serve as a safe, efficient nanocarrier to effectively inhibit the growth and spread of primary tumors.
Third, a new metal-based supramolecular polymer was synthesized using a simple and breakthrough strategy from uracil-functionalized polypropylene glycol precursors and divalent mercury ions. The presence of the supramolecular polymers leads the complex to self-assembled into uniformly nanosized spherical micelles. Moreover, the coordination of Hg2+ ions into the supramolecular polymer structure provides additional advantages such as high structural stability under physiological environment, and ultra-sensitive pH-responsive Hg2+ release due to dissociation of metal-polymer bond and unique fluorescence emission behaviors. Interestingly, cytotoxic and fluorescence studies confirm that Hg-BU-PPG exhibit cancer cell-selective internalization and cytotoxic effects and minimum toxicity towards the normal cells, these makes the micelle attractive anticancer nanoplatform. In addition, Flow cytometry study using double staining agents confirm that Hg-BU-PPG micelles demonstrate ultra-high apoptosis of cancer cells while keeping normal cells safe due to cancer cell-selective endocytosis of the micelles. Thus, our investigation implies a new approach for the development of safe and efficient drug-free metal containing supramolecular nanocarrier for enhanced treatment of cancer.

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