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研究生:劉宜璇
研究生(外文):Yi-Syuan Liou
論文名稱:利用萘酐衍生物探索細胞內多胺以及有機奈米結構之構築
論文名稱(外文):Intracellular Polyamine Exploration and Organic Nanostructure Construction Based on 1,8-Naphthalic Anhydride Derivatives.
指導教授:張健忠
口試委員:廖國智謝文俊
口試日期:2016-07-20
學位類別:碩士
校院名稱:國立中興大學
系所名稱:生醫工程研究所
學門:工程學門
學類:生醫工程學類
論文種類:學術論文
論文出版年:2016
畢業學年度:104
語文別:中文
論文頁數:79
中文關鍵詞:Heck反應Suzuki反應多胺(polyamine)粒線體奈米結構自我組裝分子內電荷轉移
外文關鍵詞:Heck reactionSuzuki reactionpolyaminemitochondriananostructureself-assemblyintramolecular charge transfer
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本論文利用Heck與Suzuki反應方法合成一系列4號位置取代之1, 8-naphthalic anhydride 衍生物,並分為兩部分討論。第一部分中化合物S1及S2能在室溫與一級胺快速反應;由光譜觀察到化合物S1及S2對於胺基酸中的Lysine(Lys)和Arginine(Arg)有很好的反應選擇性及靈敏度,並導致系統的螢光從無到有。在細胞影像的觀察可以發現化合物S1與S2會存在於細胞的粒線體中。推測是因為粒線體本身為鹼性環境而且還會有多胺(polyamine)的作用發生。Polyamine現象對於細胞的生長及分化扮演著不可或缺的角色,我們期望可以藉由化合物S1與S2來檢測Polyamine以及過度表現Polyamine的細胞。第二部分是探討具不同推拉電子能力的化合物N1, N2, N3與N4在水-有機溶劑混合溶液中其自我組裝成奈米結構的行為。實驗中藉著溶劑比例的改變可以調控化合物的自我組裝能力以獲得不同型態的奈米結構(包括奈米粒、奈米纖維及奈米薄片)。此法製備方式簡單,無須外加誘導因子,最重要的是這些奈米結構具有螢光特性,使其應用性更大。實驗利用螢光顯微鏡、掃描式電子顯微鏡與分子的溶劑效應所得的分子內電荷轉移 (intramolecular charge transfer, ICT) 能力來探討奈米結構與分子自我組裝的機制。

In this work, we design and synthesize a series of 4-aryl substituted of 1, 8-naphthalic anhydride derivatives and classified to separate section base on their optical properties application. The first section describes the development of polyamine overexpress biosensors. Spectral studies indicated that derivatives S1 and S2 can conjugate arginine and lysine with high selectivity and sensitivity, which ascribed to the primary amine-reaction condition, therefore lead to the fluorescence turn-on of the system. Moreover, the cellular imaging reveals that S1 and S2 can specifically localize on the mitochondria of living cells. Combine the pH-dependent sensing assay, we infer that S1 and S2 should conjugate with intracellular polyamine and can be used to explore the polyamines related cell growth. Eventually, amino acid probe S1 can be applied to be the polyamine overexpress cancer cell marker. The second section in this thesis we explore the nanostructure construction capabilities for a series of electron push-pull conjugated compounds N1, N2, N3 and N4 in water/THF mixed solution. The self-assemble behaviors were assessed by changing the water/THF ratio and concentrations compounds. We found that the self-assembled ability can be regulated to obtain different types of nanostructures (including nanoparticle, nanofiber and nanosheet). This protocol is very convenient because there is external inducing factor, adjuvant reagent and redox reagent, with respect to the preparation of metal nanostructures. The most important is that these organic nanostructures offer the bright emissions, which extend the applications. Fluorescence microscope, powder x-ray and SEM were used to characterize the nanostructure and the intramolecular charge transfer (ICT) was to investigate the mechanism of molecular self-assembly.

致謝……………………………………………………………………………… i

中文摘要………………………………………………………………………… ii

英文摘要………………………………………………………………………… iii

第一章 研發特定胺基酸之螢光探針並用來探討細胞中的多胺表現
一、前言
1.1診斷………………………………………………………………………… 1
1.2分子影像…………………………………………………………………… 2
1.3多胺………………………………………………………………………… 3
1.4研究動機…………………………………………………………………… 7
二、實驗
2.1材料與藥品………………………………………………………………… 8
2.2儀器與設備………………………………………………………………… 8
2.3實驗方法…………………………………………………………………… 9
2.4分子合成與鑑定…………………………………………………………… 11
三、結果與討論
3.1基本光譜…………………………………………………………………… 14
3.2胺基酸檢測………………………………………………………………… 20
3.3反應機制…………………………………………………………………… 32
3.4細胞餵養情形……………………………………………………………… 36
3.5細胞內定位………………………………………………………………… 43
3.6 Polyamine………………………………………………………………… 44
3.6.1長時間觀察…………………………………………………………… 44
3.6.2 短時間觀察…………………………………………………………… 44
四、結論………………………………………………………………………… 47
第二章多樣化的有機奈米結構
一、前言
1.1奈米材料…………………………………………………………………… 48
1.2各種奈米材料的特性及應用……………………………………………… 49
1.2.1零維-奈米粒………………………………………………………… 49
1.2.2一維-奈米纖維……………………………………………………… 51
1.2.2.1奈米管…………………………………………………………… 51
1.2.2.2奈米線…………………………………………………………… 51
1.2.3二維-奈米薄膜……………………………………………………… 51
1.2.4三維-奈米塊材……………………………………………………… 52
1.3研究動機…………………………………………………………………… 53
二、實驗
2.1分子的合成與鑑定………………………………………………………… 54
2.2實驗方法…………………………………………………………………… 56
三、結果與討論
3.1基本光譜…………………………………………………………………… 57
3.2 AIEE測試…………………………………………………………………… 62
3.3螢光顯微鏡………………………………………………………………… 67
3.4 SEM………………………………………………………………………… 67
四、結論………………………………………………………………………… 76
五、參考文獻…………………………………………………………………… 77


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