合成含腺嘌呤核苷之新型奈米碳管

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姓名

李柔盈(Rou-ying Li) 查詢紙本館藏

畢業系所

化學學系

論文名稱

合成含腺嘌呤核苷之新型奈米碳管
(Incorporation of Multiple Adenosines onto Carbon Nanotubes)

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★ 設計及合成含藥物之新穎鉑錯合物

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摘要(中)

近年來，奈米碳管已經被廣泛的應用在藥物載體方面，相較於傳統經血液循環使藥物分散於身體各器官，它可作為藥物載體投遞藥物至目標細胞或器官中，以避免藥物未到達目標細胞時即被免疫系統給代謝掉，提高藥效，因此實驗室設計一含腺嘌呤核苷衍生物之新型奈米碳管，其可作為辨認DNA序列之高專一性載體，將藥物準確投遞至目標細胞，降低藥物之副作用並提高疾病治癒效果。
　　其欲修飾至奈米碳管之腺嘌呤核苷衍生物，為利用3’’-O-[(tert-butyl)-di-methylsilyl]-2’’-deoxyadenosine (14)與9-azido-4,7-dioxanonanoic acid (7)進行酯化反應，得到具有azide官能基之5’’-O-(9-azido-4,7-dioxanonanyl)-2’’-deoxy-adenosine (16)。另一方面我們利用p-amino phenyl propargyl ether (19)進行官能基化修飾三鍵基團於奈米碳管上，接著藉由Click化學反應，使其具有azide官能基之腺嘌呤與奈米碳管上之三鍵進行銜接，合成含腺嘌呤核苷衍生物之新型奈米碳管 (2)。
　　並藉由紅外線光譜儀、拉曼散射儀器、熱重量損失分析儀及高解析掃描穿透式電子顯微鏡證實已成功得到腺嘌呤核苷衍生物之新型奈米碳管，重要的為Click反應產率為77%，相較於先前實驗室之Click產率提升兩倍，更加印證Click反應產率高、簡單且選擇性好，因而得到高效率之腺嘌呤核苷衍生物奈米碳管，此官能基化之奈米碳管即可應用於辨認疾病目標序列，成為高專一性之藥物投遞載體，優點為可接合上辨認不同疾病之DNA特殊序列，治癒更多疾病，並提高治療效果降低副作用，給予病患治療疾病一線生機。

摘要(英)

Carbon nanotubes with their unique pseudo-one-dimensional nanostructures and related electronic, optical, and mechanical properties have been attracting much attention for potential biological applications, such as biosensors, bio-delivery, bio imaging and so on. Recently, carbon nanotubes have been explored as multipurpose innovative carriers for drug delivery and diagnostic applications. In this thesis, recent studies and advances toward bioapplications of carbon nanotubes are reviewed, followed by detailed reports on my research project concerning the use of stable complexes between carbon nanotubes and DNA for gene therapeutic capacity are mentioned.
　　In our project, we used 3’’-O-[(tert-butyl)dimethylsilyl]-2’’-deoxyadenosine (14) and 9-azido-4,7-dioxanonanoic acid (7) as our starting materials. The reaction with the adenosine derivative gave 5’’-O-(9-azido-4,7-dioxanonanyl)-2’’-deoxyadenosine (16). After that we successfully functionalized the carbon nanotubes by using the p-amino phenyl propargyl ether (19). Finally the functionalized carbon nanotube derivative (1) coupled with 5’’-O-(9-azido-4,7-dioxanonanyl)-2’’-deoxyadenosine (16) by using click reaction results multi-adenosine derivatives on to carbon nanotubes (2).
　　Then we used infrared spectroscopy, Raman spectra, thermogravimetric analysis spectra and HRSTEM spectra to confirm wrapping of multi-adenosine derivatives on to carbon nanotubes. Importantly, when we compared to previous data that the click reaction yield is enhanced to 77%. It indicates that the click reaction is simple and good selectivity with high efficiency. The functionalised carbon nanotubes has high specificity in drug delivery and targetting DNA sequence. The functionalised carbon nanotubes has the advantage to cure the diseases in efficient way with less side effects.

關鍵字(中)

★ 去氧核醣核酸
★ 奈米碳管
★ 藥物載體
★ 腺嘌呤核苷

關鍵字(英)

★ Adenosines
★ DNA
★ drug delivery
★ carbon nanotubes

論文目次

目錄
中文摘要 ................................................. i
英文摘要 ............................................... iii
縮寫對照表 ............................................... v
謝誌 .................................................... vi
目錄 ................................................... vii
圖目錄 .................................................. xi
表目錄 ................................................. xiv
一、緒論 .......................................... 1
二、結果 .......................................... 5
2-1　合成具有azide及polyethylene glycol骨架之連結衍生物... 5
2-2　合成具有TBDMS及Boc保護基的腺嘌呤核苷衍生物........... 6
2-3　合成N6,N6-Bis[(tert-butoxy)carbonyl]-5'-O-(9-azido-4,7-dioxanonanyl)-2'-deoxyadenosine (13) ..................... 7
2-4　合成5'-O-(9-Azido-4,7-dioxanonanyl)-2'-deoxyadenosine (16) ..................................................... 9
2-5　合成具有三鍵官能基之奈米碳管 (1) ................... 10
2-6　合成含腺嘌呤核苷衍生物之新型奈米碳管 (2) ........... 18
三、討論 ......................................... 23
3-1　無法從N6,N6-Bis[(tert-butoxy)carbonyl]-5'-O-(9-azido-4,7-di-oxanonanyl)-2'-deoxyadenosine (13)中去除保護基之探討....................................................... 23
3-2　利用共價鍵結(covalently)或非共價鍵結(noncovalently)方式
官能基化修飾奈米碳管差異之探討........................... 25
3-3　三鍵官能基化奈米碳管及含腺嘌呤核苷衍生物之新型奈米碳
管傅立葉轉換紅外線光譜儀之探討.......................... 26
3-4　三鍵官能基化奈米碳管及含腺嘌呤核苷衍生物之新型奈米碳
管拉曼散射圖譜之探討.................................... 28
3-5　三鍵官能基化奈米碳管及含腺嘌呤核苷衍生物之新型奈米碳
管重量百分比之探討...................................... 30
3-6　含腺嘌呤核苷衍生物之新型奈米碳管上腺嘌呤核苷衍生物
間距之探討............................................... 32
3-7　提升腺嘌呤核苷衍生物於奈米碳管表面佔有比例之探討.... 36
3-8　三鍵官能基化奈米碳管及含腺嘌呤核苷衍生物之新型奈米
碳管高解析掃描穿透式電子顯微鏡圖譜之探討................. 38
3-9　未修飾之奈米碳管、三鍵官能基化之奈米碳管及含腺嘌呤核
苷衍生物之新型奈米碳管溶解度之探討.................. 40
四、結論 ......................................... 43
五、實驗部分 ................................... 44
N6,N6-Bis[(tert-butoxy)carbonyl]-5'-O-(9-azido-4,7-dioxanonanyl)-3'-O-[(tert-butyl)dimethylsilyl]-2'-deoxyadenosine (12)...................................... 45
N6,N6-Bis[(tert-butoxy)carbonyl]-5'-O-(9-azido-4,7-dioxanonanyl)-2'-deoxyadenosine (13) .................... 46
5'-O-(9-Azido-4,7-dioxanonanyl)-3'-O-[(tert-butyl)dimethylsilyl]-2'-deoxyadenosine (15).................... 46
5'-O-(9-Azido-4,7-dioxanonanyl)-2'-deoxyadenosine (16)... 47
Adenosine derivatives-functionalized carbon nanotubes (2)...................................................... 48
六、參考文獻 ................................... 49
七、光譜 ......................................... 55
N6,N6-Bis[(tert-butoxy)carbonyl]-5'-O-(9-azido-4,7-dioxanonanyl)-3'-O-[(tert-butyl)dimethylsilyl]-2'-deoxyadenosine (12) 1H NMR............................... 56
N6,N6-Bis[(tert-butoxy)carbonyl]-5'-O-(9-azido-4,7-dioxanonanyl)-3'-O-[(tert-butyl)dimethylsilyl]-2'-deoxyadenosine (12) 13C NMR.............................. 56
N6,N6-Bis[(tert-butoxy)carbonyl]-5'-O-(9-azido-4,7-dioxanonanyl)-3'-O-[(tert-butyl)dimethylsilyl]-2'-deoxyadenosine (12) IR圖譜............................... 57
N6,N6-Bis[(tert-butoxy)carbonyl]-5'-O-(9-azido-4,7-dioxanonanyl)-2'-deoxyadenosine (13) 1H NMR.............. 57
N6,N6-Bis[(tert-butoxy)carbonyl]-5'-O-(9-azido-4,7-dioxanonanyl)-2'-deoxyadenosine (13) 13C NMR............. 58
N6,N6-Bis[(tert-butoxy)carbonyl]-5'-O-(9-azido-4,7-dioxanonanyl)-2'-deoxyadenosine (13) IR圖譜.............. 58
5'-O-(9-Azido-4,7-dioxanonanyl)-3'-O-[(tert-butyl)dimethylsilyl]-2'-deoxyadenosine (15) 1H NMR............. 59
5'-O-(9-Azido-4,7-dioxanonanyl)-3'-O-[(tert-butyl)dimethylsilyl]-2'-deoxyadenosine (15) 13C NMR............ 59
5'-O-(9-Azido-4,7-dioxanonanyl)-3'-O-[(tert-butyl)dimethylsilyl]-2'-deoxyadenosine (15) IR圖譜............. 60
5'-O-(9-Azido-4,7-dioxanonanyl)-2'-deoxyadenosine (16) 1H NMR...................................................... 60
5'-O-(9-Azido-4,7-dioxanonanyl)-2'-deoxyadenosine (16) 13C NMR...................................................... 61
5'-O-(9-Azido-4,7-dioxanonanyl)-2'-deoxyadenosine (16) IR圖譜....................................................... 61
圖目錄
Figure 1. 三鍵官能基化奈米碳管1之IR圖譜.................. 12
Figure 2. 三鍵官能基化奈米碳管1之拉曼圖譜................ 13
Figure 3. 三鍵官能基化奈米碳管1之熱重量損失分析圖譜...... 14
Figure 4. 未修飾奈米碳管(比例尺20 nm)之高解析掃描穿透式
電子顯微鏡圖譜........................................... 15
Figure 5. 未修飾奈米碳管(比例尺100 nm)之高解析掃描穿透式
電子顯微鏡圖譜........................................... 15
Figure 6. 三鍵官能基化奈米碳管1(比例尺為20 nm)之高解析掃
描穿透式電子顯微鏡圖譜................................... 16
Figure 7. 三鍵官能基化奈米碳管1(比例尺為100 nm)之高解析掃
描穿透式電子顯微鏡圖譜................................... 16
Figure 8. 未修飾奈米碳管於DMF溶劑中之分散情形............ 17
Figure 9. 三鍵官能基化奈米碳管於DMF溶劑中之分散情形...... 18
Figure 10.含腺嘌呤核苷衍生物之新型奈米碳管2之IR圖譜...... 20
Figure 11.含腺嘌呤核苷衍生物之新型奈米碳管2之拉曼圖譜.... 20
Figure 12.含腺嘌呤核苷衍生物之新型奈米碳管2熱重量損失分析圖譜....................................................... 21
Figure 13.含腺嘌呤核苷衍生物之新型奈米碳管2 (比例尺為20 nm)
之高解析掃描穿透式電子顯微鏡圖譜......................... 21
Figure 14.含腺嘌呤核苷衍生物之新型奈米碳管2 (比例尺為20 nm)
之高解析掃描穿透式電子顯微鏡圖譜......................... 22
Figure 15.含腺嘌呤核苷衍生物之新型奈米碳管2於DMF溶劑中之分散情形..................................................... 22
Figure 16. Liu, Z.教授團隊於2008年所發表之藉由吸附能力修飾奈米碳管示意圖............................................. 25
Figure 17. Ojima, I.教授團隊於2008年所發表之藉由共價鍵結方式
修飾奈米碳管示意圖....................................... 26
Figure 18.未修飾奈米碳管 (a)、三鍵官能基化奈米碳管1 (b)、含腺嘌呤核苷衍生物之新型奈米碳管2 (c)之傅立葉轉換紅外線光譜疊圖....................................................... 27
Figure 19.未修飾奈米碳管 (a)、三鍵官能基化奈米碳管1 (b)、含腺嘌呤核苷衍生物之新型奈米碳管2 (c)之拉曼散射疊圖........ 29
Figure 20.未修飾奈米碳管 (a)、三鍵官能基化奈米碳管1 (b)、含腺嘌呤核苷衍生物之新型奈米碳管2 (c)之熱重量損失分
析圖譜疊圖............................................... 30
Figure 21.含腺嘌呤核苷衍生物之新型奈米碳管2上腺嘌呤核苷衍
生物間距模型............................................. 32
Figure 22.利用多項式回歸方法算出42個碳及54個碳中心至邊界
距離(α) ................................................ 34
Figure 23.腺嘌呤核苷衍生物之間距示意圖................... 35
Figure 24.含腺嘌呤核苷衍生物之新型奈米碳管2與DNA序列纏繞情形之示意圖................................................. 36
Figure 25.未修飾奈米碳管 (a, b)、三鍵官能基化奈米碳管1 (c, d)、含腺嘌呤核苷衍生物之新型奈米碳管2 (e, f)高解析掃描穿透式電子顯微鏡圖譜........................................... 39
Figure 26.未修飾奈米碳管 (1)、三鍵官能基化奈米碳管1 (2)、含腺嘌呤核苷衍生物之新型奈米碳管2 (3)於DMF溶劑中之分散情形....................................................... 41
表目錄
Table 1. 去Boc保護基的反應條件........................... 23
Table 2. 利用不同層數之六圓環算出平均碳數及中心至邊界距離(α)..................................................... 33

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指導教授

胡紀如(Jih Ru Hwu)

審核日期

2011-7-24

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