Dr. Yoshinori Ohsumi, the 2016 Nobel Prize Winner in Physiology and Medicine, reported autophagy - a cellular physiological phenomenon of a highly conserved pathway for degradation. It was immediately considered as a new strategy for cancer treatment and therefore attention by scientists to study the details of its mechanism. Therefore, the understanding of biomolecular interactions in autophagy becomes very critical and the development of organic dyes with specific functionality is an important but challenging task.
In this study, elegant syntheses of heterocyclic molecules structure were first reported and endowed specific photophysical properties to enable the in vivo bioimaging. According to the results of simulation, a series of DQI derivatives with tailored emission wavelengths ranging from 450 to 700 nm have been designed and synthesized. To selectively monitor organelles of interest, four of the above derivatives were selected and used in the construction of subcellular localized small molecule fluorescent probes. Successfully, lysosome tracker probes (Lyso-DQI), mitochondria tracker probe (Mito-DQI), endoplasmic reticulum tracker probe (ER-DQI) and plasma membrane tracker probe (PM-DQI) have been developed and all well agreed with commercially available organelle trackers. In addition, a series of fluorescent probes with adjustable emission synthesized in this work could be excited by a single wavelength, which allow a multiple targeting of biomolecules of interest. Finally, the DQI probes developed in this study promised an in vivo monitoring of mitochondrial autophagy under hypoxic conditions.
論文審定書........................................................................................................i
論文公開授權書...............................................................................................ii
論文提要..........................................................................................................iii
序文與致謝......................................................................................................iv
中文摘要...........................................................................................................v
Abstract............................................................................................................vi
目錄.................................................................................................................vii
圖目錄...............................................................................................................x
表目錄...........................................................................................................xvii
流程圖目錄..................................................................................................xviii
縮寫表............................................................................................................xxi
第一章 緒論......................................................................................................1
1.1 光學成像與生醫影像 ( Optical Imagine and Biomedical Imaging )........1
1.1.1 單一活細胞成像 ( Live Single Cell Image ).............................................3
1.1.2 螢光成像顯影試劑 ( Fluorescent Imaging Agent )...............................5
1.1.3 螢光標記基團 ( Fluorescent Labeling Group ).....................................13
1.1.4 螢光探針設計 ( Modular Design of Fluorescent Probes )....................44
1.1.5 胞器成像螢光探針 ( Fluorescent Probes for Organelle Imaging )......58
1.1.6 細胞螢光影像的現況與挑戰................................................................72
1.2 研究動機...................................................................................................73
1.2.1 實驗室已開發之雜環分子合成方法....................................................73
1.2.2 研究目標................................................................................................81
第二章 研究過程與結果討論........................................................................83
2.1 銠（II）催化的脫氮環化法合成四氫喹啉並應用於天然物之類似物的合成.................................................................................................................83
2.1.1 四氫喹啉核心的天然物結構與其生物活性........................................83
2.1.2 文獻已知的四氫喹啉核心結構合成方法............................................84
2.1.3 Ts-triazole benzylamine (4) 的製備......................................................88
2.1.4 銠金屬催化初步測試與機制推測........................................................89
2.1.5 一鍋化的條件最佳化篩選....................................................................91
2.1.6 tetrahydroisoquinoline 衍生物的合成................................................92
2.1.7 tetrahydroisoquinoline 核心的生物鹼全合成....................................95
2.1.8 小結......................................................................................................120
2.2 金 (I) -硫醇寡聚物於水相環境中硝基芳香化合物的氫化及有機催化合成雜環的應用...............................................................................................124
2.2.1 硝基芳香族化合物還原條件的文獻探討..........................................124
2.2.2 金屬奈米粒子產氫條件的測試..........................................................125
2.2.3 利用金(I)-硫醇寡聚物進行硝基芳香化合物氫化測試與合成應用.128
2.2.4 小結......................................................................................................134
2.3 銅 (II) 催化合成二氫喹啉-4-亞胺與生醫影像試劑開發......................135
2.3.1 二氫喹啉-4-亞胺光物理性質之文獻回顧與探討............................135
2.3.2 二氫喹啉-4-亞胺光物理性質的調控................................................139
2.3.3 以二氫喹啉螢光團合成碳量子點.....................................................178
2.3.4 螢光探針之胞器顯影試劑的開發.....................................................184
2.3.5 Liposome-DQI 光物理性質的探討....................................................204
2.3.6 螢光探針之胞器染色的測試..............................................................212
2.3.7 缺氧條件下的多重胞器細胞觀察......................................................233
第三章 結論與未來展望..............................................................................240
第四章 引用文獻..........................................................................................244
第五章 實驗步驟與光譜數據......................................................................266
第六章 光譜附圖..........................................................................................433
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