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研究生： 李安湘
Lee-an xiang
論文名稱： Dendrimer Stabilized Single Walled Carbon Nanohorns as Anticancer Drug Carrier
Dendrimer Stabilized Single Walled Carbon Nanohorns as Anticancer Drug Carrier
指導教授： 今榮東洋子
Toyoko Imae
口試委員: 氏原真樹
Masaki Ujihara
吳嘉文
Chia-Wen Wu
學位類別： 碩士
Master
系所名稱： 工程學院 - 化學工程系
Department of Chemical Engineering
論文出版年： 2014
畢業學年度： 102
語文別： 英文
論文頁數： 82
中文關鍵詞： 單壁奈米碳角 、藥物傳遞 、藥物釋放 、抗癌藥物
外文關鍵詞： single walled carbon nanohorns, drug delivery, dendrimers, anticancer
相關次數： 點閱：354  下載：1 
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    • 單壁奈米碳角（SWNHs）是具嬌琴紗狀外形結構的石墨烯片，預期在藥物傳遞上有高發展性。因為單壁奈米碳角的表面改質在藥物傳遞應用中是一種重要的研究方向。此實驗中，使用酸處理作為表面改質的方法。由實驗結果可得知氧化單壁奈米碳角的最佳反應時間為2小時的酸處理反應，因為它能產生足夠的羧基及對石墨烯片有較少的破壞。因此，酸處理後的單壁奈米碳角比未經酸處理的單壁奈米碳角具有較高的分散性於水及有機溶劑中。此實驗是以單壁奈米碳角在生物應用中作為藥物遞送系統。單壁奈米碳角與葉酸（FA）結合產生分子靶應用於特定的細胞葉酸受體。此外，我們使用兩種不同官能基的樹枝狀高分子(DenOH及DenNH2)結合於單壁奈米碳角，由實驗結果可得單壁奈米碳角經由DenOH或DenNH2外層保護均可解決單壁奈米碳角與葉酸產生分散性較差的問題。而最後我們選用DenOH和單壁奈米碳角與葉酸結合，因為SWNHs-DenOH在水中相較於SWNHs-DenNH2具有較好的分散性。在此實驗中，我們選用五種抗癌藥物（替莫唑胺，酞菁，阿黴素，喜樹鹼和原卟啉），因為這五種抗癌藥物對於腫瘤具有不同的治療方法和優點。在此實驗將討論SWNHs以及SWNHs-DenOH-FA對於藥物承載的影響。在藥物乘載上SWNHs可以通過π-π作用、氫鍵與藥物連結以及將藥物載入SWNHs內部的空間，由實驗可知對於藥物上的承載能力，SWNHs-DenOH-FA比只有SWNHs更高。因為DenOH與藥物產生更多水和作用，所以會產生較佳的承載效果。而由藥物釋放曲線顯示出對於不同酸鹼度中會有不同的釋放特性，尤其在酸性環境下釋放的藥物量或會高於鹼性環境，然而SWNHs-DenOH-FA的藥物釋放量少於SWNHs，因為隨著樹枝狀大分子的相互作用與藥物產生較多的氫鍵以及產生較多的空間阻礙造成藥物較難釋放出。

    Single walled carbon nanohorns (SWNHs) is a horn-shaped sheath aggregate of graphene sheets and is expected high potential of applications including drug delivery system. Then surface modification of SWNHs is an important research direction for the adequate application. In this study, the oxidation of SWNHs was performed by acid-treatment, where 2 h reaction was preferable, because it produces enough carboxyl groups and less defect of graphene sheet. Thus acid-treated SWNHs is more dispersible in water than commercial SWNHs. The strategy in this study is biological application of SWNHs as drug delivery system. SWNHs were conjugated with folic acid (FA) molecules for targeting specific cell with folate receptors. Moreover, SWNHs were protected by poly(amido amine) (PAMAM) dendrimer for increasing poor dispersibility of SWNHs-FA. The OH-terminated PAMAM dendrimer (DenOH) is preferably used to be chemically immobilized on SWNHs than NH2-terminated Dendrimer (DenNH2), since SWNHs-DenOH shows higher dispersibility in water than SWNHs-DenNH2. Five drugs (temozolomide, phthalocyanine, doxorubicin, camptothecin and protoporphyrin) were selected as anticancer drugs in this study, because these have different therapeutic advantages and behaviors for the tumors. The controlled loading of drug on SWNHs and SWNHs-DenOH-FA carriers was investigated. The loading capacity of drug on SWNHs-DenOH-FA was always higher than on SWNHs, since DenOH gives additional hydrogen interaction with drug, while the loading of drug on SWNHs can occur via π-π stacking, hydrogen bonding and traping inside interior space. Release profile shows strong pH dependence, and drugs on SWNHs-DenOH-FA were less released than on SWNHs, because the interaction with dendrimer keeps drugs on carrier and DenOH-FA gives steric hindrance for removal of drugs.

    Abstract i 摘要 ii Acknowledgement iii Table of contents iv List of Figure vi List of Table viii Chapter 1 introduction 1 1-1 Single walled carbon nanohorns (SWNHs) 1 1-2 Poly (amido amine ) (PAMAM) dendrimers (DenNH2,DenOH) 3 1-3 Drug delivery 5 Chapter 2 Research Methodology 6 2-1 Research design 6 2-2 Materials 8 2-3 Experimental Procedures 9 2-3-1 Modification of carbon nanohorns 9 2-3-1-1 Acid-treatment and impurity removal of SWNHs 9 2-3-1-2 Chemical synthesis of hybrids of SWNHs-DenOH 10 2-3-1-3 Chemical synthesis of SWNHs-DenOH-FA 11 2-3-1-4 Chemical synthesis of hybrids of SWNHs-DenNH2 12 2-3-2 Drug loading on SWNHs and SWNHs-DenOH-FA 13 2-3-2-1 Loading of Temozolomide 13 2-3-2-2 Loading of Phthalocyanine , Doxorubicin , Camptothecin and Protoporphyrin 13 2-3-3 Drug releasing from SWNHs and SWNHs-DenOH-FA 14 2-3-3-1 Releasing in water 14 2-3-3-2 Releasing in organic solvent 14 2- 4 Instruments 15 Chapter 3 Results and Discussion 16 3-1 Effect of acid-treatment on SWNHs 16 3-1-1 Function group 16 3-1-2 Impurity removal 18 3-1-3 Defect of Graphene sheet 22 3-1-4 Morphology 24 3-1-5 conclusion 26 3-2 Dispersibility of SWNHs and it hybrids 27 3-2-1 SWNHs and SWNHs-FA 27 3-2-2 SWNHs-DenNH2 and SWNHs-DenOH 28 3-2-3 SWNHs-FA and SWNHs-DenOH-FA 33 3-2-4 conclusion 34 3-3 Characterization of SWNHs- DenOH-FA 35 3-3-1 Function group 35 3-3-2 Optical Spectroscopy 37 3-3-3 Morphology 38 3-3-4 conclusion 39 3-4 Drug loading on SWNHs or SWNHs-DenOH-FA 40 3-4-1 Loading capacity of drug 40 3-4-1-1 Temozolomide 40 3-4-1-2 Phthalocyanine 43 3-4-1-3 Doxorubicin 45 3-4-1-4 Camptothecin 48 3-4-1-5 Protoporphyrin 50 3-4-2 Comparison between SWNHs and SWNHs-DeOH-FA for drug loading 53 3-5 Drug releasing from SWNHs or SWNHs-DenOH-FA 56 3-5-1 Releasing of drug 56 3-5-1-1 Temozolomide 56 3-5-1-2 Doxourbicin 58 3-5-1-3 Phthalocyanine, Camptothecin and Protoporphyrin 60 3-5-2 Comparison of drug releasing from SWNHs and SWNHs-DenOH-FA 61 Chapter 4 General Conclusion 64 Reference 67

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