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研究生： 林妤臻
Lin, Yu-Chen
論文名稱： 藻油液胞的藥物包覆特性
Encapsulation characteristics of microalgal lipid vesicles
指導教授： 張鑑祥
Chang, Chien-Hsiang
學位類別： 碩士
Master
系所名稱： 工學院 - 化學工程學系
Department of Chemical Engineering
論文出版年： 2019
畢業學年度： 107
語文別： 中文
論文頁數： 137
中文關鍵詞： 微藻油 、液胞 、葉黃素 、膜流動性 、包覆效率
外文關鍵詞： microalgal lipid, vesicle, lutein, membrane fluidity, encapsulation efficiency
相關次數： 點閱：69  下載：4 
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    • 本研究利用由破囊弧菌萃取之兩不同批次藻油製備藥物傳輸載體，亦利用docosahexaenoic acid（DHA）製備液胞以和藻油的結果比較。所形成之液胞粒徑大約落在150～200 nm之間，界面電位呈現負值，其負電來源為脂肪酸解離。液胞之穩定天數最高可大於700天，物理穩定性佳。至於藥物包覆，嘗試利用液胞分別包覆疏水性藥物葉黃素、親水性藥物熊果素。研究中首先包覆親水性藥物熊果素，結果顯示兩批次藻油及DHA都能成功包覆，證明其皆形成液胞的結構。包覆葉黃素後液胞的粒徑明顯上升，是葉黃素分子內嵌至雙層膜中所致，界面電位些微提升則是因為部分葉黃素質子化。螢光偏極化實驗及穿透式紅外光譜顯示包覆葉黃素後，雙層膜的流動性下降，推測液胞在包覆葉黃素後應更不容易洩漏。追蹤包覆效率隨時間之變化，結果顯示包覆越高濃度的葉黃素，藻油液胞降低葉黃素降解的效果越明顯。最後，在溶血實驗及細胞活性實驗中，所有組成之液胞在低於約0.25 mM時皆可視為不具毒性。以上結果顯示藻油液胞能包覆疏水性、親水性藥物，且具有高度生物相容性，是有應用價值之藥物傳輸載體。

    In this study, two batches of fatty acid mixture cultivated from microalgae- Thraustochytrium sp. DJ3 strain were utilized to prepare drug delivery carriers. We also fabricated vesicle by docosahexaenoic acid (DHA) and compared the results with microalgal lipids. The vesicles had the size between 150 to 200 nm, while the negatively charged character could be explained by the partial dissociation of the fatty acid molecules. The vesicles could be stable up to 700 days and possessed high physical stability. As for the drug encapsulation, we tried to encapsulate hydrophobic substance-lutein and hydrophilic substance-arbutin, respectively. The successful encapsulation of arbutin by microalgal lipid carriers proved the formation of vesicular structure. For the encapsulation of lutein, the initial size increased due to the insertion of lutein molecules into the bilayer structure. The partial protonation of lutein molecules shifted the zeta potential of the vesicles to a less negative value. From both fluorescence polarization and Fourier-transform infrared spectroscopy, the bilayer fluidity decreased after encapsulating lutein, and one would expect less leakage of the vesicular structures. Tracing the variation of encapsulation efficiency through time, it was found that the higher the concentration of lutein encapsulated, the more effective the vesicles could protect lutein from degradation. In hemolysis and cell viability test, all the vesicles could be considered as non-toxic at a concentration lower than approximately 0.25 mM. The results showed that microalgal lipid vesicle was capable of encapsulating both hydrophilic and hydrophobic substances and possessed high biocompatibility. Therefore, vesicles fabricated from microalgal lipids and DHA are potential drug delivery carriers with further applications.

    總目錄 摘要 III Extended Abstract IV 誌謝 XVI 總目錄 XVII 表目錄 XXI 圖目錄 XXIV 符號說明 XXIX 第一章 緒論 1 1.1　前言 1 1-2　文獻回顧 3 1-2-1　脂肪酸液胞 3 1-2-2　微藻生產之油脂 7 1-2-3　液胞雙層膜的流動性 10 1-2-4　液胞的相轉移行為 11 1-2-5　碳鏈對稱性和鏈長的效應 15 1-2-6　疏水性藥物的包覆 16 1-2-7　葉黃素和脂肪酸載體之交互作用 18 1-2-8　生物毒性 20 1-3　研究動機與目的 21 第二章 實驗 23 2-1　藥品 23 2-2　實驗儀器及裝置 26 2-2-1　超音波震盪分散裝置 26 2-2-2　動態光散射法粒徑及界面電位分析儀 26 2-2-3　穿透式電子顯微鏡 32 2-2-4　凝膠層析管 32 2-2-5　薄膜離心過濾法 33 2-2-6　傅利葉轉換紅外光譜儀 34 2-2-7　高效能液相層析儀 37 2-2-8　螢光光譜儀 37 2-2-9　冷凍乾燥機 38 2-2-10　紫外-可見分光光度計 39 2-3　實驗方法 40 2-3-1　液胞分散液的製備 40 2-3-2　液胞粒徑分布及界面電位的量測 41 2-3-3　螢光偏極化實驗 42 2-3-4　穿透式紅外光譜的分析 42 2-3-5　葉黃素之包覆效率評估 43 2-3-6　熊果素之包覆效率評估 44 2-3-7　溶血測試 45 2-3-8　細胞活性測試 46 第三章 結果與討論 49 3-1　藻油液胞 49 3-1-1　藻油液胞的物化特性 49 3-1-2　稀釋對藻油液胞穩定性的影響 61 3-1-3　藻油液胞雙層膜的相轉移行為 67 3-1-4　藻油液胞的雙層膜流動性 70 3-1-5　藻油液胞的穩定性 71 3-2　包覆葉黃素／熊果素之藻油液胞 76 3-2-1　包覆葉黃素／熊果素對藻油液胞物化特性的影響 76 3-2-3　包覆葉黃素／熊果素對藻油液胞雙層膜流動性的影響 84 3-2-3　藻油液胞之脂溶性物質—葉黃素包覆效率 96 3-2-4　藻油液胞之水溶性物質—熊果素包覆效率 107 3-3　藻油液胞之生物相容性 109 3-3-1　藻油液胞之溶血測試 109 3-3-1　藻油液胞之細胞活性測試 112 第四章 結論 121 參考文獻 124   表目錄 表1-1　六種微藻的油脂含量（Matos, 2016）。 8 表1-2　微藻生產的油脂中DHA所佔比率。 9 表2-1　由破囊壺菌DJ3萃取之批次一（2015 batch）藻油的成分。 24 表2-2　由破囊壺菌DJ3萃取之批次二（2017 batch）藻油的成分。 25 表2-3　在亨利方程式（Henry equation）中，與κa對應的f（κa）值。 31 表2-4　以初濃度10 mM之批次一藻油液胞為例，液胞和細胞混合後濃度、細胞培養液濃度與液胞液初始添加濃度表。 48 表3-1　由藻油及DHA製備出之液胞的初始平均粒徑、粒徑分布PDI值、界面電位及穩定天數。 53 表3-2　由藻油製備出之液胞分散液的pH值。 53 表3-3　14 mM批次二藻油液胞分散液經過不同程度稀釋（2、5、10、50、100 倍）後的液胞粒徑及界面電位。 62 表3-4　8 mM DHA液胞分散液經過不同程度稀釋（2、5、10、50、100 倍）後的液胞粒徑及界面電位。 63 表3-5　不同材料所製備液胞分散液之螢光偏極化值。 70 表3-6　批次二藻油液胞以及其包覆維他命E醋酸脂後的初始平均粒徑、粒徑分布PDI值、界面電位及穩定天數。 73 表3-7　由批次一及批次二藻油製備出之包覆不同藥物液胞的初始平均粒徑、粒徑分布PDI值、界面電位及穩定天數。 78 表3-8　由DHA製備出之包覆不同藥物液胞的初始平均粒徑、粒徑分布PDI值、界面電位及穩定天數。 79 表3-9　批次二藻油液胞包覆不同濃度葉黃素#2的初始平均粒徑、粒徑分布PDI值、界面電位及穩定天數。 81 表3-10　DHA液胞包覆不同濃度葉黃素#2的初始平均粒徑、粒徑分布PDI值、界面電位及穩定天數。 82 表3-11批次二藻油液胞加入DPH前後的平均初始粒徑、粒徑分布PDI值、界面電位及穩定天數。 88 表3-12 DHA液胞加入DPH前後的平均初始粒徑、粒徑分布PDI值、界面電位及穩定天數。 89 表3-13 批次二藻油液胞以及DHA液胞包覆熊果素前後之螢光偏極化值，以360 nm為激發波長，460 nm為吸收波長。 90 表3-14 批次二藻油液胞以及DHA液胞包覆葉黃素前後之螢光偏極化值，以300 nm為激發波長，600 nm為吸收波長。 92 表3-15　批次二藻油及DHA液胞包覆熊果素／葉黃素，以穿透式紅外光譜分析法測量2920 cm-1峰值附近的波數結果。 94 表3-16　以批次一及批次二藻油液胞包覆初始添加量為0.05 mM的葉黃素#1，載體材料、製程結束後分散液中之葉黃素濃度、被包覆之葉黃素濃度、包覆效率。 100 表3-17　以批次二藻油及DHA液胞包覆初始添加量為0.05 mM的葉黃素#2，載體材料、製程結束後分散液中之葉黃素濃度、被包覆葉黃素濃度及包覆效率。 101 表3-18　以批次二藻油液胞包覆0.05、0.10、0.15、0.20、0.25、0.29 mM的葉黃素#2，初始濃度、製程結束後分散液中之葉黃素濃度、被包覆葉黃素濃度及包覆效率。 102 表3-19　DHA液胞包覆0.05、0.10、0.15、0.20、0.25、0.29 mM的葉黃素#2，初始濃度、製程結束後分散液中之葉黃素濃度、被包覆葉黃素濃度及包覆效率。 103 表3-20　批次二藻油液胞包覆0.05、0.10、0.15、0.20、0.25、0.29 mM的葉黃素#2，初始濃度及經過30天後分散液中之葉黃素濃度、被包覆之葉黃素濃度、實際包覆效率及包覆效率。 106   圖目錄 圖1-1　以脂質為材料所形成之微脂粒結構的示意圖。 1 圖1-2　界面活性劑參數與對應的結構（Segota and Tezak, 2006）。 6 圖1-3　液胞雙層膜結構隨溫度改變之情形（Heimburg, 2000）。 12 圖1-4　利用動態光散射法測量液胞相轉移溫度的示意圖（Michel et al., 2006）。 14 圖2-1　Nano ZS雷射光散射法粒徑及界面電位測定儀的量測示意圖。 27 圖2-2　動態光散射儀隨樣品濃度及粒子大小不同而調整儀器參數。 28 圖2-3　葡聚醣膠球之網狀篩孔。 33 圖2-4　薄膜離心過濾法。 34 圖2-5　可拆卸式液槽之元件組成圖。 35 圖2-6　強制型液胞分散液之製備程序。 41 圖2-7　使用毛細液膜法量測到的液胞分散液之紅外光譜圖。 43 圖3-1　左圖為穩定無聚集之樣品經過粒徑量測所得到的相關函數曲線，右圖為當樣品中有大粒子或聚集體存在時，粒徑量測分析所得到的相關函數曲線。 49 圖3-2　由左至右分別為10 mM第一批次藻油、14 mM第二批次藻油、8 mM DHA所製備出的液胞分散液外觀。 54 圖3-3　10 mM批次一藻油所製備出液胞的初始粒徑分布。 55 圖3-4　14 mM批次二藻油所製備出液胞的初始粒徑分布。 56 圖3-5　DHA所製備出液胞的初始粒徑分布。 56 圖3-6　10 mM批次一藻油所製備出液胞的粒徑分布隨時間的變化。 57 圖3-7　14 mM批次一藻油所製備出液胞的粒徑分布隨時間的變化。 58 圖3-8　8 mM DHA所製備出液胞的粒徑分布隨時間的變化。 59 圖3-9　14 mM批次二藻油所製備出液胞的TEM影像。 60 圖3-10　14 mM批次二藻油液胞分散液（a）原液（14 mM）、（b）經稀釋2倍（7 mM）、（c）5倍（2.8 mM）、（d）10倍（1.4 mM）、（e）50倍（0.28 mM）、（f）100倍（0.14 mM）的液胞初始粒徑分布。 64 圖3-11　8 mM DHA液胞分散液（a）原液（8 mM）、（b）經稀釋2倍（4 mM）、（c）5倍（1.6 mM）、（d）10倍（0.8 mM）、（e）50倍（0.16 mM）的液胞初始粒徑分布。 65 圖3-12　8 mM DHA液胞分散液原液（8 mM）、經稀釋2倍（4 mM）、5倍（1.6 mM）、10倍（0.8 mM）、50倍（0.16 mM）、100倍（0.08 mM）後的外觀。 66 圖3-13　批次二藻油液胞以DLS進行（a）升溫、（b）降溫測量及DHA液胞以DLS進行（c）升溫、（d）降溫測量所得粒徑與count rate對溫度作圖的結果。 69 圖3-14　批次二藻油液胞分散液在製備完成5天內（左）以及300天後（右）的外觀。 72 圖3-15　（a）14 mM批次二藻油液胞粒徑分布隨時間變化圖。（b）14 mM批次二藻油液胞包覆維他命E醋酸脂後粒徑分布隨時間變化圖。 74 圖3-16　（a）14 mM批次二藻油液胞吸光值隨時間變化圖。（b）14 mM批次二藻油液胞加入維他命E醋酸脂後吸光值隨時間變化圖。 75 圖3-17　由左而右分別為批次二藻油液胞未包覆藥物、包覆熊果素、包覆葉黃素#1之液胞分散液外觀。 80 圖3-18　由左而右分別為14 mM批次二藻油液胞包覆0.05 、 0.10 、 0.15 、 0.20 、 0.25 、 0.29 mM葉黃素#2之液胞分散液外觀。 80 圖3-19　（a）批次二藻油液胞包覆不同濃度葉黃素之粒徑及界面電位的改變。（b）DHA液胞包覆不同濃度葉黃素粒徑以及界面電位的改變。 83 圖3-20　（a）DPH、（b）葉黃素、（c）批次二藻油、（d）DHA及（e）熊果素之吸收圖譜，縱軸為吸光值，橫軸為波長。 91 圖3-21　（a）DPH及（b）葉黃素之UV-Vis吸收圖譜，以及其所放出螢光的大約波長位置。 93 圖3-22　批次二藻油液胞包覆（a）30 mM熊果素、（b）0.05 mM葉黃素#2、（c）0.29 mM葉黃素#2，以及DHA液胞包覆（d）30 mM熊果素、（e）0.05 mM葉黃素#2、（f）0.29 mM葉黃素#2，使用DLS測量所得粒徑及derived count rate對溫度作圖。 95 圖3-23　（a）批次二藻油液胞對葉黃素之包覆效率對葉黃素濃度作圖，（b）DHA液胞對葉黃素之包覆效率對葉黃素濃度作圖。 104 圖3-24　（a）被包覆之葉黃素濃度隨時間變化，（b）液胞分散液內葉黃素濃度隨時間變化，（c）被包覆之葉黃素及液胞分散液內葉黃素濃度的疊圖分析。 105 圖3-25　（a）批次一藻油液胞及其分別包覆葉黃素#1、熊果素之溶血率對濃度作圖（b）批次二藻油液胞及其分別包覆葉黃素#2、熊果素之溶血率對濃度作圖（c）DHA液胞及其分別包覆葉黃素#2、熊果素之溶血率對濃度作圖 111 圖3-26　（a）批次一藻油液胞及其分別包覆葉黃素#1、熊果素的液胞，（b）批次二藻油液胞及其分別包覆葉黃素#2、熊果素的液胞及（c）DHA液胞及其分別包覆葉黃素#2、熊果素的液胞，以BEAS-2B細胞測試之細胞存活率對濃度作圖。 113 圖3-27　批次一藻油液胞及其分別包覆葉黃素#1、熊果素後與BEAS-2B細胞作用後在倒立式光學顯微鏡下之影像。 114 圖3-28　批次二藻油液胞及其分別包覆葉黃素#2、熊果素後與BEAS-2B細胞作用後在倒立式光學顯微鏡下之影像。 115 圖3-29　DHA液胞及其分別包覆葉黃素#2、熊果素後與BEAS-2B細胞作用後在倒立式光學顯微鏡下之影像。 116 圖3-30　（a）批次一藻油液胞及其分別包覆葉黃素、熊果素的液胞，（b）批次二藻油液胞及其分別包覆葉黃素、熊果素的液胞及（c）DHA液胞及其分別包覆葉黃素、熊果素的液胞，以H1299細胞測試之細胞存活率對濃度作圖。 117 圖3-31　批次一藻油液胞及其分別包覆葉黃素、熊果素後與H1299細胞作用後在倒立式光學顯微鏡下之影像。 118 圖3-32　批次二藻油液胞及其分別包覆葉黃素、熊果素後與H1299細胞作用後在倒立式光學顯微鏡下之影像。 119 圖3-33　DHA液胞及其分別包覆葉黃素、熊果素後與H1299細胞作用後在倒立式光學顯微鏡下之影像。 120  

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