以毛細管電泳法與電灑游離質譜法探討內包錯合物之研究

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姓名

陳玫慧(Mei-Hui Chen) 查詢紙本館藏

畢業系所

化學學系

論文名稱

以毛細管電泳法與電灑游離質譜法探討內包錯合物之研究
(Application of Capillary electrophoresis and Electrospray Ionization Mass Spectrometry to study of Inclusion Complexes)

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摘要(中)

內包錯合物（inclusion complexes）或主-客錯合物（host-guest complexes）之間的作用機制是由一個具有空腔結構的主分子與一個客分子錯合形成非共價鍵錯合物（non-covalent bond complex）。一般常見的主分子（host molecule）為冠狀醚類（crown ether）、環芃（cyclophane）和環糊精（cyclodextrin，CD），而環糊精為最常被使用。
在適當的條件下，毛細管環糊精修飾電泳法能有效分離七種萘磺酸鹽位置異構物，然而對於位置異構物與環糊精之錯合情形和遷移行為並不完全了解。因此，希望利用毛細管環糊精修飾電泳法進一步了解環糊精與位置異構物在水溶液中之鍵結作用情形，並估算多種分析物與環糊精在水溶液中之結合常數。因毛細管電泳法不能得知環糊精與分析物是以何種化學計量形成內包錯合物（如1：1或1：2的結合），且缺乏分子量和結構資訊，因此可利用電灑游離質譜法（Electrospray Ionization Mass Spectrometry，ESI-MS）來量測內包錯合物之分子離子峰以補足此缺點。
電灑游離質譜法屬於一種較溫和、低能量的游離方法，測定非共價鍵錯合物時，可以直接量測整體錯合物的分子離子峰，由信號強弱，可得知非共價鍵相互作用力的相對強度。本研究利用環糊精作為酵素模型，可先模擬?-、?-、或?-環糊精與萘磺酸鹽類位置異構物間相互作用力，在ESI-MS質譜圖中可得知環糊精與萘磺酸鹽類位置異構物，會形成1：1化學計量之錯合物。此外，從結合常數及質譜圖中可得知，?-環糊精對磺酸鹽類位置異構物是最具有選擇性；而?-環糊精對磺酸鹽類位置異構物的選擇性是最差的。且取代基在b位置的磺酸鹽類位置異構物與環糊精具有較好之結合作用力。利用毛細管電泳法量測結合常數，若搭配ESI-MS技術準確地檢測內包錯合物的總分子量，可以更確認內包錯合物的形成機制。

摘要(英)

The formation of non-covalent inclusion complexes, also called host-guest complexes, was complexation between guest analyte and host molecule which was a truncated cone with a hollow cylindrical cavity in the center. Generally, most used host molecules were crown ethers, cyclophanes, and cyclodextrins（CDs）. And CDs were commonly used host molecules.
In suitable condition, seven positional naphthalenesulfonate isomers could be separated by Capillary Electrophoresis （CE）. However, the behavior of migration and complexation between isomers and CDs didn’t be understood clearly. CE could be used simultaneously to determine the formation constants of a set of analytes in a mixed solution. The interaction of naphthalenesulfonate derivatives with CDs and the inclusion complex formation constants were evaluated in more detail. Due to lacking of molecular weight and structure information CE could not provide. Electrospray ionization mass spectrometry (ESI-MS) was used to study the non-covalent bond complexes complementally.
The gentle ionization process of ESI allowed the intact complexes to be directly detected by mass spectrometry. Stoichiometry of the complex could be easily obtained from the mass spectrum which showed the molecular weight of the complex. CDs have been frequently used as enzyme models, which could simulate the interaction between ?-、?-、?-CD and positional naphthalenesulfonate isomers. The ESI-MS spectrum results showed that the most stable inclusion complexes were formed with 1：1 Stoichiometry. Furthermore, formation constants and mass spectra proved that inclusion complexes between ?-position substituted analytes and ?-CD enhanced the stability of complexes greatly. The formation constants of analytes were successfully studied by CE, and the combination of using ESI-MS technique for detection of the non-covalent bond complexes molecular weight confirmed the formation of inclusion complexes advancedly to complement the CE method.

關鍵字(中)

★ 內包錯合物

關鍵字(英)

★ inclusion complexes

論文目次

中文摘要 -------------------------------------------------------------------- Ⅰ
英文摘要 -------------------------------------------------------------------- Ⅲ
目錄 -------------------------------------------------------------------------- Ⅴ
表目錄 ----------------------------------------------------------------------- Ⅷ
圖目錄 --------------------------------------------------------------------- Ⅹ
第一章前言 -------------------------------------------------------------- 1
1-1 研究的緣起 --------------------------------------------------------- 1
1-2 研究目標 ------------------------------------------------------------ 2
第二章文獻回顧 ------------------------------------------------------- 6
2-1 毛細管電泳的歷史背景和發展 --------------------------------- 6
2-2 毛細管電泳的分離原理 ------------------------------------------ 9
2-2-1 荷電粒子在電泳的遷移行為 ---------------------------- 9
2-2-2 電滲透流與電荷粒子的遷移行為 ---------------------- 10
2-2-3 分離效率與解析度 ---------------------------------------- 16
2-3 毛細管電泳儀之裝置 --------------------------------------------- 18
2-4 毛細管電泳分離模式 -------------------------------------------- 19
2-5 影響毛細管電泳現象的因素 ----------------------------------- 20
2-6 進樣方式 --------------------------------------------------------- 22
2-6-1 電動力進樣法 -------------------------------------------- 22
2-6-2 水動力進樣法 --------------------------------------------- 23
2-6-3 樣品堆積 --------------------------------------------------- 24
2-7 電灑游離法 --------------------------------------------------------- 24
2-8 環糊精 --------------------------------------------------------------- 26
2-9 分析物在環糊精下的遷移行為 --------------------------------- 31
2-10 內包錯合物 ------------------------------------------------------ 35
2-11 萘磺酸鹽類 ------------------------------------------------------ 39
第三章實驗步驟與樣品分析 -------------------------------------- 42
3-1 實驗藥品與儀器設備 --------------------------------------------- 42
3-1-1實驗藥品 ----------------------------------------------------- 42
3-1-2 儀器設備 ---------------------------------------------------- 44
3-2 實驗步驟 ------------------------------------------------------------ 45
3-2-1 萘磺酸鹽（NS）異構物分析 ----------------------------- 45
3-2-1.1 標準品的製備 ------------------------------------- 45
3-2-1.2 緩衝溶液的製備 ---------------------------------- 45
3-2-1.3 毛細管的處理 -------------------------------------- 45
3-2-1.4 實驗操作條件 -------------------------------------- 47
第四章結果與討論 ---------------------------------------------------- 49
4-1 環糊精對NS位置異構物分離影響 ---------------------------- 49
4-1-1 毛細管環糊精修釋區帶電泳之分離 ------------------- 49
4-1-2 緩衝溶液之pH值的影響 -------------------------------- 58
4-2 萘磺酸鹽位置異構物與環糊精的結合常數之測定 --------- 67
4-3 以ESI-MS分析環糊精非共價鍵內包錯合物 ---------------- 72
4-3-1 單一磺酸根取代基萘磺酸鹽與?-環糊精錯合之情形 72
4-3-2 含一胺基、雙磺酸根取代基萘磺酸鹽與?-環糊精錯合之
情形 -------------------------------------------------------- 73
4-3-3 雙磺酸根取代基萘磺酸鹽與?-環糊精錯合之情形 -- 73
4-3-4 萘磺酸鹽位置異構物與混合之?-、?-及?-環糊精錯合
之情形 ----------------------------------------------------- 86
第五章結論 ----------------------------------------------------------- 103
參考文獻 --------------------------------------------------------------- 104
附錄 ---------------------------------------------------------------------- 117
A-1 萘磺酸鹽類之性質與特性 ------------------------------------- 117
A-2 對於偵測環境中aromatic sulfonates 的方法 -------------- 119
A-3 萘磺酸鹽類與環糊精及MH形成錯合物之ESI質譜圖 ---------------- 123
表目錄
表1-1. 萘磺酸鹽類之結構式，縮寫及其波峰之符號代號 -------- 5
表2-1. 毛細管區帶電泳中各種電滲透流之控制變因 ------------- 15
表2-2. 環糊精的性質 ---------------------------------------------------- 30
表3-1. 毛細管電泳儀（CE）設定參數 ------------------------------ 47
表3-2. 電灑游離質譜法（ESI-MS）設定參數 ------------------------ 48
表4-1. 添加環糊精之萘磺酸鹽位置異構物之遷移時間（硼酸鹽緩衝溶液，pH 9.2）--------------------------- 57
表4-2. 添加環糊精之萘磺酸鹽位置異構物之遷移時間（硼酸鹽緩衝溶液，pH 9.2）--------------------------- 57
表4-3. 理論板數（theoretical plate，N） ------------- 65
表4-4. 添加環糊精之萘磺酸鹽位置異構物的遷移時間（硼酸鹽緩衝溶液，pH 3.0） --------------------------- 66
表4-5. 添加環糊精之萘磺酸鹽位置異構物的遷移時間（磷酸鹽緩衝溶液，pH 3.0） --------------------------- 66
表4-6. 位置異構物與環糊精之結合常數和電泳遷移率 ---------- 71
表4-7. 環糊精內包錯合物之相對強度 ------------------------------- 84
表4-8. 萘磺酸鹽位置異構物與環糊精及MH形成錯合物之R值 -------------------------------- 85
表4-9. 環糊精與N-1-S和N-2-S形成錯合物之分子離子------------------- 96
表4-10. 環糊精與2NH2-1,5-DS和3NH2-2,7-DS形成錯合物之分子離子 --------------- 97
表4-11. 環糊精與N-1,5-DS、N-1,6-DS及N-2,6-DS形成錯合物之分子離子 ------------ 98
表4-12. N-1-S和N-2-S與環糊精形成內包錯合物之相對強度 --- 99
表4-13. 2NH2-1,5-DS和3NH2-2,7-DS與環糊精形成內包錯合物 --100
表4-14. N-1,5-DS、N-1,6-DS及N-2,6-DS與環糊精與N-1,5-DS形成錯合物 -------------- 101
表4-15.萘磺酸鹽位置異構物與環糊精形成錯合物之R值 ------------- 102
圖目錄
圖2-1. 毛細管柱內壁表面矽醇基Si-OH解離示意圖 ----------- 10
圖2-2. 毛細管內壁之Stern電雙層模型 ---------------------------- 11
圖2-3. 毛細管內之電位變化圖 ---------------------------------------- 12
圖2-4. 電滲透流存在下的速度 ---------------------------------------- 14
圖2-5. 毛細管區帶電泳法之示意圖 ---------------------------------- 14
圖2-6. 流體流動剖面圖 ------------------------------------------------- 16
圖2-7. 毛細管電泳儀裝置圖 ------------------------------------------- 18
圖2-8. 環糊精結構通式 ------------------------------------------------- 29
圖2-9. 偶氮染料分解反應式 ------------------------------------------- 40
圖4-1. 以一般CZE分離方法分離萘磺酸鹽位置異構物之電泳圖（硼酸鹽緩衝溶液，pH 9.2） ----------- 50
圖4-2. 不同濃度的環糊精對萘磺酸鹽位置異構物分離效果的影響之電泳圖 -------------------------- 54
圖4-3. 不同濃度的環糊精對萘磺酸鹽位置異構物分離效果的影響之電泳圖 ------------------- 55
圖4-4. 不同濃度的環糊精對萘磺酸鹽位置異構物分離效果的影響之電泳圖 ------------------------ 56
圖4-5. 以一般CZE分離方法分離萘磺酸鹽位置異構物之電泳圖（磷酸鹽緩衝溶液，pH 3.0） ---------- 61
圖4-6. 不同濃度的環糊精對萘磺酸鹽位置異構物分離效果的影響之電泳圖 -------------------------- 62
圖4-7. 不同濃度的環糊精對萘磺酸鹽位置異構物分離效果的影響之電泳圖 --------------------------- 63
圖4-8. 不同濃度的環糊精對萘磺酸鹽位置異構物分離效果的影響之電泳圖 --------------------------- 64
圖4-9. N-1-S與環糊精形成錯合物之ESI質譜圖 --------------- 75
圖4-10. N-2-S與環糊精形成錯合物之ESI質譜圖 --------------- 76
圖4-11. 2NH2-N-1,5-DS與環糊精形成錯合物之ESI質譜圖 ---- 77
圖4-12. 3NH2-N-2,7-DS與環糊精形成錯合物之ESI質譜圖 ---- 78
圖4-13. N-1,5-DS與環糊精形成錯合物之ESI質譜圖 ------------ 79
圖4-14. N-1,6-DS與環糊精形成錯合物之ESI質譜圖 ------------ 80
圖4-15. N-2,6-DS與環糊精形成錯合物之ESI質譜圖 ------------ 81
圖4-16. MH的結構式 ----------------------------------------------------- 85
圖4-17. N-1-S與環糊精形成錯合物之ESI質譜圖 ------------------ 89
圖4-18. N-2-S與環糊精形成錯合物之ESI質譜圖 --------------------- 90
圖4-19. 2NH2-N-1,5-DS與環糊精形成錯合物之ESI質譜圖 ----------------------------------------------------- 91
圖4-20. 3NH2-N-2,7-DS與環糊精形成錯合物之ESI質譜圖 ------------------------------- 92
圖4-21. N-1,5-DS與環糊精形成錯合物之ESI質譜圖 -------------------------------------- 93
圖4-22. N-1,6-DS與環糊精形成錯合物之ESI質譜圖 ----------------------------------- 94
圖4-23. N-2,6-DS與環糊精形成錯合物之ESI質譜圖 ------------------------------------- 95
圖4-24. N-1-S與環糊精形成錯合物之ESI質譜圖 -------------- 123
圖4-25. N-2-S與環糊精形成錯合物之ESI質譜圖 -------------- 124
圖4-26. 2NH2-N-1,5-DS與環糊精形成錯合物之ESI質譜圖 -- 124
圖4-27. 3NH2-N-2,7-DS與環糊精形成錯合物之ESI質譜圖 -- 125
圖4-28. N-1,5-DS與環糊精形成錯合物之ESI質譜圖 ---------- 125
圖4-29. N-1,6-DS與環糊精形成錯合物之ESI質譜圖 ---------- 126
圖4-30. N-2,6-DS與環糊精形成錯合物之ESI質譜圖 ---------- 126
圖4-31. N-1-S與環糊精形成錯合物之ESI質譜圖 --------------- 127
圖4-32. N-2-S與環糊精形成錯合物之ESI質譜圖 -------------- 127
圖4-33. 2NH2-N-1,5-DS與環糊精形成錯合物之ESI質譜圖 -- 128
圖4-34. 3NH2-N-2,7-DS與環糊精形成錯合物之ESI質譜圖 -- 128
圖4-35. N-1,5-DS與環糊精形成錯合物之ESI質譜圖 ---------- 129
圖4-36. N-1,6-DS與環糊精形成錯合物之ESI質譜圖 ---------- 129
圖4-37. N-2,6-DS與環糊精形成錯合物之ESI質譜圖 ---------- 130
圖4-38. N-1-S與MH形成錯合物之ESI質譜圖 ------------------- 131
圖4-39. N-2-S與MH形成錯合物之ESI質譜圖 ------------------- 131
圖4-40. 2NH2-N-1,5-DS與MH形成錯合物之ESI質譜圖 ------- 132
圖4-41. 3NH2-N-2,7-DS與MH形成錯合物之ESI質譜圖 ------- 132
圖4-42. N-1,5-DS與MH形成錯合物之ESI質譜圖 --------------- 133
圖4-43. N-1,6-DS與MH形成錯合物之ESI質譜圖 --------------- 133
圖4-44. N-2,6-DS與MH形成錯合物之ESI質譜圖 --------------- 134

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指導教授

丁望賢(Wang-Hsien Ding)

審核日期

2004-6-28

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