簡易檢索 / 詳目顯示

研究生: 陳冠丞
Chen, Kuan-Cheng
論文名稱: 三碳鏈離子對雙親分子形成之陰陽離子液胞的物化特性及維他命E醋酸酯包覆效率
Physicochemical properties and vitamin E acetate encapsulation efficiency of catanionic vesicles fabricated from triple-chained ion pair amphiphiles
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: 110
中文關鍵詞: 離子對雙親分子陰陽離子液胞雙層膜流動性維他命E醋酸酯包覆效率細胞毒性測試溶血測試
外文關鍵詞: Ion pair amphiphile, Catanionic vesicle, Vitamin E acetate, Encapsulation efficiency, Cytotoxicity assay, Hemolysis assay
相關次數: 點閱:206下載:13
分享至:
查詢本校圖書館目錄 查詢臺灣博碩士論文知識加值系統 勘誤回報
  • 本研究以雙碳鏈陽離子型界面活性劑dihexadecyldimethylammonium bromide(DHDAB)分別與單鏈陰離子型界面活性劑sodium hexadecylsulfate(SHS)、sodium dodecylsulfate(SDS)所形成之兩種三碳鏈離子對雙親分子( ion pair amphiphile, IPA )DHDA-HS和DHDA-DS為主材料,添加雙十六烷基磷酸(dihexadecyl phosphate, DHDP)使液胞帶負電,並以強制型製程製備出陰陽離子液胞,分析其物理性質、相轉移行為、雙層膜流動性及維他命E醋酸酯之包覆效率。此外,探討包覆維他命E醋酸酯後液胞雙層膜流動性之變化,並作細胞活性及溶血測試,以評估應用於藥物載體的可行性。
    實驗結果顯示,純成分DHDA-HS可形成液胞,而足夠的碳鏈間凡得瓦力及液胞電性使其有良好的穩定性,由於SHS對水的溶解度較DHDAB高,故較易溶解出雙層膜而使液胞帶正電。添加雙鏈陰離子界面活性劑DHDP後,所形成之液胞的粒徑稍微下降,電性由正電轉變為負電,依然具有良好穩定性。螢光偏極化法的分析結果顯示,10 mol%及20 mol% DHDP添加下液胞雙層膜之相轉移行為非常相似,相轉移溫度則稍微下降。此外,由紅外光譜法分析碳氫鏈的自由度,添加10 mol%及20 mol% DHDP後,碳氫鏈排列呈不規則,此現象可能和DHDP及HS頭基間斥力有關。
    在藥物包覆實驗中,DHDA-HS/DHDP (莫耳比8/2)與DHDA-DS/DHDP (莫耳比8/2)液胞系統包覆維他命E醋酸酯後,粒徑隨維他命E醋酸酯濃度增加逐漸上升至持平,而由於維他命E醋酸酯本身不帶電,故電性並無太大變化。比較兩個陰陽離子液胞系統對維他命E醋酸酯的包覆效率,DHDA-HS系統略高於DHDA-DS系統,可能和其疏水空間較多有關。紅外光譜法的結果顯示,包覆維他命E醋酸酯後,碳氫鏈排列呈規則特性,表示雙層膜流動性降低。此外,兩個陰陽離子液胞系統亦可包覆親水性藥物熊果素,證明兩個三鏈離子對雙親分子系統可形成液胞結構。
    為了評估液胞包覆藥物後的應用性也進行細胞活性測試, DHDA-DS/DHDP(莫耳比8/2)液胞系統在包覆維他命E醋酸酯後,人類非小細胞肺癌細胞株(H1299)與正常人類上皮細胞(BEAS-2B)的存活率皆明顯提升,在液胞濃度低於0.5 mM時,細胞存活率皆高於80%,可視為低毒性。溶血測試結果也顯示液胞包覆維他命E醋酸酯後,溶血率有下降的趨勢。

    In this study, two triple-chained ion pair amphiphiles, dihexadecyldimethylammonium-hexadecylsulfate (DHDA-HS) and dihexadecyldimethylammonium-dodecylsulfate (DHDA-DS) were prepared from double-chain cationic surfactant, dihexadecyldimethylammonium bromide (DHDAB), with single-chain anionic surfactants, sodium hexadecylsulfate (SHS) and sodium dodecylsulfate (SDS). With the consideration of drug delivery applications, dihexadecyl phosphate (DHDP) was added into DHDA-HS and DHDA-DS respectively. First, DHDA-HS can be fabricated as positively charged catanionic vesicles with the size of 130nm. With addition of DHDP, the size of DHDA-HS vesicle turned from 130nm into 100nm with negative charge. In addition, DHDA-HS/DHDP vesicle had high physical stability. Membrane characteristic was analyzed by fluorescence polarization and infrared spectroscopy. Infrared spectroscopy analysis revealed that increasing content of DHDP causes the arrangement of hydrocarbon chain more disordered, and fluorescence polarization analysis indicated the phase transition temperature was decreased. On drug encapsulation, DHDA-HS/DHDP vesicle and DHDA-DS/DHDP vesicle both could encapsulate hydrophobic drug, vitamin E acetate efficiently. In addition, with the successful encapsulation of hydrophilic drug, arbutin, it was proved that the DHDA-HS/DHDP and DHDA-DS/DHDP vesicles indeed possessed vesicular structures. BEAS-2B cells and H1299 cells were used to conduct the cytotoxicity assay for the vitamin E acetate encapsulated vesicles. The results indicated that the increased content of vitamin E acetate reduced the cytotoxicity and the hemolysis test also showed the vitamin E acetate encapsulation could cause hemolysis ratio decrease.

    總目錄 摘要 I Extended Abstract III 誌謝 XII 總目錄 XIII 表目錄 XVII 圖目錄 XX 符號說明 XXIV 第一章 緒論 1 1-1 前言 1 1-2 研究動機與目的 4 1-3 文獻回顧 5 1-3-1 離子對雙親分子 5 1-3-2 陰陽離子液胞 6 1-3-3 帶電液胞 8 1-3-4 液胞的相轉移行為 10 1-3-5 利用三碳鏈之雙親分子製備的液胞 12 1-3-6 碳鏈對稱性和鏈長的效應 14 1-3-7 疏水性藥物之包覆 16 1-3-8 細胞毒性 18 第二章 實驗方法 20 2-1 藥品 20 2-2 實驗儀器及裝置 20 2-2-1 超音波震盪分散裝置 20 2-2-2 雷射光散射法粒徑及界面電位分析儀 21 2-2-3 元素分析儀 25 2-2-4 穿透式電子顯微鏡 26 2-2-5 傅利葉轉換紅外光譜儀 26 2-2-6 螢光光譜儀 28 2-2-7 凝膠層析管 29 2-2-8 高效能液相層析儀 30 2-2-9 倒立光學顯微鏡 30 2-2-10 連續波長微量盤分光光譜儀 31 2-3 實驗方法 32 2-3-1 離子對雙親分子的製備 32 2-3-2 液胞分散液的製備 33 2-3-3 液胞粒徑分布及界面電位的量測 35 2-3-4 穿透式紅外光譜的分析 35 2-3-5 螢光偏極化實驗 36 2-3-6 藥物包覆效率的計算 37 2-3-7 細胞活性測試 38 2-3-8 溶血測試 43 第三章 結果與討論 44 3-1 離子對雙親分子DHDA-HS及DHDA-DS 44 3-1-1 元素分析 44 3-1-2 界面活性劑參數 45 3-2 DHDA-HS之陰陽離子液胞系統 47 3-2-1 DHDA-HS之陰陽離子液胞的物理特性 47 3-2-2 DHDA-HS/DHDP之陰陽離子液胞的物理特性 51 3-2-3 DHDA-HS/DHDP液胞雙層膜的相轉移行為 58 3-2-4 DHDP對DHDA-HS系統雙層膜排列的影響 63 3-3 三碳鏈系統之陰陽離子液胞包覆親疏水性藥物 65 3-3-1 DHDA-HS/DHDP與DHDA-DS/DHDP液胞包覆維他命E醋酸酯後的物理性質 65 3-3-2 DHDA-HS/DHDP與DHDA-DS/DHDP液胞的維他命E醋酸酯包覆效率 74 3-3-3 包覆維他命E醋酸酯對液胞雙層膜排列的影響 78 3-3-4 DHDA-HS/DHDP與DHDA-DS/DHDP液胞的熊果素包覆效率 80 3-4 細胞活性與溶血檢測 82 3-4-1 細胞活性檢測 82 3-4-2 包覆維他命E醋酸酯之液胞對H1299細胞的毒性檢測 83 3-4-3 包覆維他命E醋酸酯之液胞對BEAS-2B細胞的毒性測試 86 3-4-4 包覆維他命E醋酸酯之液胞的溶血測試 90 第四章 結論 92 參考文獻 94

    參考文獻
    Aiello, C., Andreozzi, P., La Mesa, C. and Risuleo, G., “Biological activity of SDS-CTAB cat-anionic vesicles in cultured cells and assessment of their cytotoxicity ending in apoptosis,” Colloids and surfaces B:Biointerfaces, 78, 2, 149-154, 2010.
    Ali, M. H., Moghaddam, B., Kirby, D. J., Mohammed, A. R. and Perrie, Y., “The role of lipid geometry in designing liposomes for the solubilisation of poorly water soluble drugs,” International Journal of Pharmaceutics, 453, 1, 225-232, 2013.
    Ang, I. A., “含對稱雙十二碳鏈離子對雙親分子及帶負電脂質之陰陽離子液胞的物理穩定性及維他命E醋酸酯包覆效率,” 國立成功大學化學工程學系碩士論文, 2011.
    Bernsdorff, C., and Winter, R, “Differential properties of the sterols cholesterol, ergosterol, beta-sitosterol, trans-7-dehydrocholesterol, stigmasterol and lanosterol on DPPC bilayer order,” Journal of Physical Chemistry B, 107, 38, 10658-10664, 2003.
    Bhattacharya, S., De, S. M. and Subramanian, M., “Synthesis and vesicle formation from hybrid bolaphile/amphiphile ion-pairs. Evidence of membrane property modulation by molecular design,” Journal of Organic Chemistry, 63, 22, 7640-7651, 1998.
    Bhattacharya, S. and Haldar, S., “Interactions between cholesterol and lipids in bilayer membranes. Role of lipid headgroup and hydrocarbon chain-backbone linkage,” Biochimica et Biophysica Acta-Biomembranes, 1467, 1, 39-53, 2000.
    Blandamer, M. J., Briggs, B., Cullis, P. M., Rawlings, B. J. and Engberts, J., “Vesicle - cholesterol interactions: Effects of added cholesterol on gel-to-liquid crystal transitions in a phospholipid membrane and five dialkyl-based vesicles as monitored using DSC,” Physical Chemistry Chemical Physics, 5, 23, 5309-5312, 2003.
    Blanzat, M., Perez, E., Rico-Lattes, I., Prome, D., Prome, J. C. and Lattes, A., “New catanionic glycolipids. 1. Synthesis, characterization, and biological activity of double - chain and gemini catanionic analogues of galactosylceramide (gal beta(1)cer),” Langmuir, 15, 19, 6163-6169, 1999.
    Brasher, L. L., Herrington, K. L. and Kaler, E. W., “Electrostatic effects on the phase - behavior of aqueous cetyltrimethylammonium bromide and sodium octyl sulfate mixtures with added sodium-bromide,” Langmuir, 11, 11, 4267-4277, 1995.
    Brito, R. O., Marques, E. F., Silva, S. G., do Vale, M. L., Gomes, P., Araujo, M. J., Rodriguez-Borges, J. E., Infante, M. R., Garcia, M. T., Ribosa, I., Vinardell, M. P., Mitjans, M., “Physicochemical and toxicological properties of novel amino acid-based amphiphiles and their spontaneously formed catanionic vesicles,” Colloids and Surfaces B-Biointerfaces, 72, 1, 80-87, 2009.
    Bui, T. T., Suga, K., and Umakoshi, H., “Roles of sterol derivatives in regulating the properties of phospholipid bilayer systems,” Langmuir, 32, 24, 6176-6184, 2016.
    Cagdas, M. F., Ertugral, N., Bucak, S., and Atay, N. Z., “Effect of preparation method and cholesterol on drug encapsulation studies by phospholipid liposomes,” Pharmaceutical Development and Technology, 16, 4, 408-414, 2011..
    Campbell, R. B., Balasubramanian, S. V. and Straubinger, R. M., “Phospholipid - cationic lipid interactions: influences on membrane and vesicle properties,” Biochimica et Biophysica Acta - Biomembranes, 1512, 1, 27-39, 2001.
    Carmona - Ribeiro, A. M., Ortis, F., Schumacher, R. I. and Armelin, M. C. S., “Interactions between cationic vesicles and cultured mammalian cells,” Langmuir, 13, 8, 2215-2218, 1997.
    Carrion, F. J., Delamaza, A. and Parra, J. L., “The influence of ionic-strength and lipid bilayer charge on the stability of liposomes,” Journal of Colloid and Interface Science, 164, 1, 78-87, 1994.
    Chien, C. L., Yeh, S. J., Yang, Y. M., Chang, C. H. and Maa, J. R., “Formation and encapsulation of catanionic vesicles,” Journal of the Chinese Colloid and Interface Society, 24, 31-45, 2002.
    Chiruvolu, S., Israelachvili, J. N., Naranjo, E., Xu, Z., Zasadzinski, J. A., Kaler, E. W. and Herrington, K. L., “Measurement of forces between spontaneous vesicle-forming bilayers,” Langmuir, 11, 11, 4256-4266, 1995.
    Chou, T. H., Liang, C. H., Lee, Y. C. and Yeh, L. H., “Effects of lipid composition on physicochemical characteristics and cytotoxicity of vesicles composed of cationic and anionic dialkyl lipids,” Physical Chemistry chemical Physics, 16, 4, 1545-1553, 2014.
    Chung, M. H. and Chung, Y. C., “Polymerized ion pair amphiphile that shows remarkable enhancement in encapsulation efficiency and very slow release of fluorescent markers,” Colloids and Surfaces B - Biointerfaces, 24, 2, 111-121, 2002.
    Chung, M. H., Park, C., Chun, B. C. and Chung, Y. C., “Polymerized ion pair amphiphile vesicles with pH-sensitive transformation and controlled release property,” Colloids and Surfaces B - Biointerfaces, 34, 3, 179-184, 2004.
    Chung, M. H., Park, M. J., Chun, B. C. and Chung, Y. C., “Encapsulation and permeation properties of the polymerized ion pair amphiphile vesicle that has an additional carboxyl group on anionic chain,” Colloids and Surfaces B - Biointerfaces, 28, 2-3, 83-93, 2003.
    Dhawan, V. V. and Nagarsenker, M. S., “Catanionic systems in nanotherapeutics - Biophysical aspects and novel trends in drug delivery applications,” Journal of Controlled Release, 266, 331-345, 2017.
    Eastman, S. J., Siegel, C., Tousignant, J., Smith, A. E., Cheng, S. H. and Scheule, R. K., “Biophysical characterization of cationic lipid: DNA complexes,” Biochimica et Biophysica Acta - Biomembranes, 1325, 1, 41-62, 1997.
    Evans, D. F. and Wemmerström, H., “The Colloidal Domain: Where Physics, Chemistry, Biology, and Technology Meet,” VCH, New York, 110-114, 1994.
    Feitosa, E., Jansson, J. and Lindman, B., “The effect of chain length on the melting temperature and size of dialkyldimethylammonium bromide vesicles,” Chemistry and Physics of Lipids, 142, 1-2, 128-132, 2006.
    Fischer, A., Hebrant, M. and Tondre, C., “Glucose encapsulation in catanionic vesicles and kinetic study of the entrapment/release processes in the sodium dodecyl benzene sulfonate/cetyltrimethylammonium tosylate/water system,” Journal of Colloid and Interface Science, 248, 1, 163-168, 2002.
    Fukuda, H., Kawata, K., Okuda, H. and Regen, S. L., “Bilayer-forming ion-pair amphiphiles from single-chain surfactants,” Journal of the American Chemical Society, 112, 4, 1635-1637, 1990.
    Gunarsa, C. A., “含雙十六碳鏈磷酸鹽之陰陽離子液胞的物理穩定性及維他命E包覆效率,” 國立成功大學化學工程學系碩士論文, 2010.
    Haas, S., Hoffmann, H., Thunig, C., and Hoinkis, E., “Phase and aggregation behaviour of double-chain cationic surfactants from the class of N-alkyl-N-alkyl'-N, N-dimethylammonium bromide surfactants,” Colloid and Polymer Science, 277, 9, 856-867, 1999.
    Hac-Wydro, K., Wydro, P. and Dynarowicz-Latka, P., “Interactions between dialkyldimethylammonium bromides (DXDAB) and sterols - a monolayer study,” Journal of Colloid and Interface Science, 286, 2, 504-510, 2005.
    Heimburg, T., “A model for the lipid pretransition: coupling of ripple formation with the chain - melting transition,” Biophysical Journal, 78, 3, 1154-1165, 2000.
    Hirano, K., Fukuda, H. and Regen, S. L., “Polymerizable ion-paired amphiphiles,” Langmuir, 7, 6, 1045-1047, 1991.
    Holmberg, K., “Handbook of applied surface and colloid chemistry. Volume 2, ” John Wiley & Sons Ltd., Baffins Lane, Chichester, West Sussex PO19 IUD, England, 47-48, 2002.
    Hong, S. S., Kim, S. H. and Lim, S. J., “Effects of triglycerides on the hydrophobic drug loading capacity of saturated phosphatidylcholine-based liposomes,” International Journal of Pharmaceutics, 483, 1-2, 142-150, 2015.
    Huang, C. J., Quinn, D., Sadovsky, Y., Suresh, S., and Hsia, K. J., “Formation and size distribution of self-assembled vesicles,” Proceedings of the National Academy of Sciences of the United States of America, 114, 11, 2910-2915, 2017.
    ISO 10993-5:2009 Biological Evaluation of Medical Devices. Part 5: Tests for In Vitro Cytotoxicity; International Organization for Standardization: Geneva, Switzerland, 2009.
    Israelachvili, J. N., Mitchell, D. J. and Ninham, B. W., “Theory of self-assembly of hydrocarbon amphiphiles into micelles and bilayers,” Journal of the Chemical Society-Faraday Transactions Ii, 72, 1525-1568, 1976.
    Jubeh, T. T., Barenholz, Y. and Rubinstein, A., “Differential adhesion of normal and inflamed rat colonic mucosa by charged liposomes,” Pharmaceutical Research, 21, 3, 447-453, 2004.
    Kaler, E. W., Murthy, A. K., Rodriguez, B. E. and Zasadzinski, J. A. N., “Spontaneous vesicle formation in aqueous mixtures of single-tailed surfactants,” Science, 245, 4924, 1371-1374, 1989.
    Keough, K. M. W. and Davis, P. J., “Gel to liquid-crystalline phase-transitions in water dispersions of saturated mixed-acid phosphatidylcholines,” Biochemistry, 18, 8, 1453-1459, 1979.
    Kida, T., Tanaka, T., Nakatsuji, Y. and Akashi, M., “Formation of micrometer-sized supramolecular assemblies with unique morphologies from triple-chain lipids with two sugar head groups,” Chemistry Letters, 35, 1, 112-113, 2006.
    Kondo, Y., Uchiyama, H., Yoshino, N., Nishiyama, K. and Abe, M., “Spontaneous vesicle formation from aqueous-solutions of didodecyldimethylammonium bromide and sodium dodecyl-sulfate mixtures,” Langmuir, 11, 7, 2380-2384, 1995.
    Kranenburg, M., and Smit, B., “Phase behavior of model lipid bilayers,” Journal of Physical Chemistry B, 109, 14, 6553-6563, 2005.
    Kuo, A.-T., Chang, C.-H., Shinoda, W., “Molecular dynamics study of catanionic bilayers composed of ion pair amphiphile with double-tailed cationic surfactant,” Langmuir 28, 8156-8164, 2012.
    Kuo, A. T. and Chang, C. H., “Cholesterol-induced condensing and disordering effects on a rigid catanionic bilayer: a molecular dynamics study,” Langmuir, 30, 1, 55-62, 2014.
    Lasic, D. D., “Liposomes: from physics to applications,” Elsevier Amsterdam, New York, 265-318, 1993.
    Lasic, D. D. and Papahadjopoulos, D., “Liposomes and biopolymers in drug and gene delivery,” Current Opinion in Solid State & Materials Science, 1, 3, 392-400, 1996.
    Lasic, D. D., “Liposomes in gene delivery,” CRC press, New York, 67-112, 1997.
    Lee, W. H., Tang, Y. L., Chiu, T. C. and Yang, Y. M., “Synthesis of ion-pair amphiphiles and calorimetric study on the gel to liquid-crystalline phase transition behavior of their bilayers,” Journal of Chemical and Engineering Data, 60, 4, 1119-1125, 2015.
    Li, F., Luan, Y., Liu, X., Pang, J., Lin, G., Shao, W. and Li, Z., “Characterization and aggregation behaviors of mixed DDAB/SDS solution with and without poly(4-styrenesulfonic acid-co-maleic acid) sodium,” Journal of Dispersion Science and Technology, 32, 11, 1624-1633, 2011.
    Liang, C. H. and Chou, T. H., “Effect of chain length on physicochemical properties and cytotoxicity of cationic vesicles composed of phosphatidylcholines and dialkyldimethylammonium bromides,” Chemistry and Physics of Lipids, 158, 2, 81-90, 2009.
    Lopes, S., Neves, C., Eaton, P. and Gameiro, P., “Cardiolipin, a key component to mimic the E. coli bacterial membrane in model system membranes,” Biophysical Journal, 100, 3, 626-626, 2011.
    Manohar, C, and Narayanan, J., “Average packing factor approach for designing micelles, vesicles and gel phases in mixed surfactant systems,” Colloids and Surfaces A-Physicochemical and Engineering Aspects, 403, 129-132, 2012.
    Marques, E. F., Brito, R. O., Silva, S. G., Rodriguez-Borges, J. E., do Vale, M. L., Gomes, P., Araujo, M. J., Soderman, O. “Spontaneous vesicle formation in catanionic mixtures of amino acid-based surfactants: Chain length symmetry effects,” Langmuir, 24, 19, 11009-11017, 2008.
    Marques, E. F., Regev, O., Khan, A. and Lindman, B., “Self-organization of double-chained and pseudodouble-chained surfactants: counterion and geometry effects,” Advances in Colloid and Interface Science, 100, 83-104, 2003.
    Massey, J. B., “Interfacial properties of phosphatidylcholine bilayers containing vitamin E derivatives,” Chemistry and Physics of Lipids, 109, 2, 157-174, 2001.
    McMullen, T. P. W., Lewis, R. and McElhaney, R. N., “Differential scanning calorimetric study of the effect of cholesterol on the thermotropic phase - behavior of a homologous series of linear saturated phosphatidylcholines,” Biochemistry, 32, 2, 516-522, 1993.
    McMullen, T. P. W., Lewis, R. and McElhaney, R. N., “Differential scanning calorimetric and Fourier transform infrared spectroscopic studies of the effects of cholesterol on the thermotropic phase behavior and organization of a homologous series of linear saturated phosphatidylserine bilayer membranes,” Biophysical Journal, 79, 4, 2056-2065, 2000.
    Mel'nikova, Y. S., Mel'nikov, S. M. and Lofroth, J. E., “Physico-chemical aspects of the interaction between DNA and oppositely charged mixed liposomes,” Biophysical Chemistry, 81, 2, 125-141, 1999.
    Merino - Montero, S., Montero, M. T. and Hernandez - Borrell, J., “Effects of lactose permease of Escherichia coli on the anisotropy and electrostatic surface potential of liposomes,” Biophysical Chemistry, 119, 1, 101-105, 2006.
    Michel, N., Fabiano, A. S., Polidori, A., Jack, R. and Pucci, B., “Determination of phase transition temperatures of lipids by light scattering,” Chemistry and Physics of Lipids, 139, 1, 11-19, 2006.
    Morgan, M., Aramaki, Y., and Tsuchiya, S., “Biochemical characterisation of polycation-induced cytotoxicity to human vascular endothelial cells,” Journal of Cell Science 94, 553-559, 1989.
    Mukerjee, P. and Mysels, K.J., “Critical Micelle Concentrations of Aqueous Surfactant Systems,” National Bureau of Standards, 20234, 77, 1971.
    Nogueira-Pedro, A., Barbosa, C.M., Segreto, H.R., Lungato, L., D’Almeida, V., et al., “Alpha-Tocopherol induces hematopoietic stem/-progenitor cell expansion and ERK1/2-mediated differentiation,” Journal of Leukocyte Biology, 90, 1111–1117, 2011.
    New, R. R. C., “Liposomes: a practical approach,” Oxford University Press, New York, 1-32, 1990.
    Panda, A. K., Possmayer, F., Petersen, N. O., Nag, K. and Moulik, S. P., “Physico - chemical studies on mixed oppositely charged surfactants: Their uses in the preparation of surfactant ion selective membrane and monolayer behavior at the air water interface,” Colloids and Surfaces A - Physicochemical and Engineering Aspects, 264, 1-3, 106-113, 2005.
    Pucci, C., Scipioni, A., Diociaiuti, M., La Mesa, C., Perez, L., and Pons, R., “Catanionic vesicles and DNA complexes: a strategy towards novel gene delivery systems,” RSC Advances, 5, 99, 81168-81175, 2015.
    Saito, S., “Solubilities of ionic surfactants in aqueous polymer solutions,” Kolloid-Zeitschrift and Zeitschrift Fur Polymere, 215, 1, 16-21, 1967.
    Schindler, H. and Seelig, J., “Deuterium order parameters in relation to thermodynamic properties of a phospholipid bilayer. Statistical mechanical interpretation,” Biochemistry, 14, 11, 2283-2287, 1975.
    Segota, S. and Tezak, D., “Spontaneous formation of vesicles,” Advances in Colloid and Interface Science, 121, 1-3, 51-75, 2006.
    Singh, M., McKenzie, K. and Ma, X., “Effect of dimethyl sulfoxide on in vitro proliferation of skin fibroblast cells,” Journal of Biotech Research, 8, 78-82, 2017.
    Song, Y. K. and Liu, D. X., “Free liposomes enhance the transfection activity of DNA/lipid complexes in vivo by intravenous administration,” Biochimica et Biophysica Acta - Biomembranes, 1372, 1, 141-150, 1998.
    Soussan, E., Mille, C., Blanzat, M., Bordat, P. and Rico-Lattes, I., “Sugar-derived tricatenar catanionic surfactant: synthesis, self-assembly properties, and hydrophilic probe encapsulation by vesicles,” Langmuir, 24, 2326-2330, 2008.
    Sumida, Y., Masuyama, A., Maekawa, H., Takasu, M., Kida, T., Nakatsuji, Y., Ikeda, I. and Nojima, M., “Stable vesicles made from new triple-chain amphiphiles: long-term stability toward leakage of the trapped substances,” Chemical Communications, 21, 2385-2386, 1998.
    Sumida, Y., Masuyama, A., Takasu, M., Kida, T., Nakatsuji, Y., Ikeda, I. and Nojima, M., “Behavior of self-organized molecular assemblies composed of phosphatidylcholines and synthetic triple-chain amphiphiles in water,” Langmuir, 16, 21, 8005-8009, 2000.
    Sumida, Y., Masuyama, A., Takasu, M., Kida, T., Nakatsuji, Y., Ikeda, I. and Nojima, M., “New pH-sensitive vesicles. Release control of trapped materials from the inner aqueous phase of vesicles made from triple-chain amphiphiles bearing two carboxylate groups,” Langmuir, 17, 3, 609-612, 2001.
    Tomasic, V., Stefanic, I. and Filipovic-Vincekovic, N., “Adsorption, association and precipitation in hexadecyltrimethylammonium bromide/sodium dodecyl sulfate mixtures,” Colloid and Polymer Science, 277, 2-3, 153-163, 1999.
    Tabandeh, H. and Mortazavi, S, A., “An Investigation into Some Effective Factors on Encapsulation Efficiency of Alpha-Tocopherol in MLvs and the Release Profile from the Corresponding Liposomal Gel,” Iranian Journal of Pharmaceutical Rearch, 12, 21-30, 2013.
    Tondre, C. and Caillet, C., “Properties of the amphiphilic films in mixed cationic/anionic vesicles: a comprehensive view from a literature analysis,” Advances in Colloid and Interface Science, 93, 1-3, 115-134, 2001.
    Uemura, M., Manabe, H., Yoshida, N., Fujita, N., Ochiai, J., Matsumoto, N., Takagi, T., Naito, Y. and Yoshikawa, T., “a-Tocopherol prevents apoptosis of vascular endothelial cells via a mechanism exceeding that of mere antioxidation,” Europen Journal of Pharmacology, 456, 29-37, 2002.
    Vautrin, C., Zemb, T., Schneider, M. and Tanaka, M., “Balance of pH and ionic strength influences on chain melting transition in catanionic vesicles,” Journal of Physical Chemistry B, 108, 23, 7986-7991, 2004.
    Vist, M. R. and Davis, J. H., “Phase-equilibria of cholesterol dipalmitoylphosphatidylcholine mixtures:deuterium nuclear magnetic resonance and differential scanning calorimetry,” Biochemistry, 29, 2, 451-464, 1990.
    Vlachy, N., Touraud, D., Heilmann, J. and Kunz, W., “Determining the cytotoxicity of catanionic surfactant mixtures on HeLa cells,” Colloids and Surfaces B:Biointerfaces, 70, 2, 278-280, 2009.
    Walker, S. A. and Zasadzinski, J. A., “Electrostatic control of spontaneous vesicle aggregation,” Langmuir, 13, 19, 5076-5081, 1997.
    Wu, C. J., Kuo, A. T., Lee, C. H., Yang, Y. M., and Chang, C. H., “Fabrication of positively charged catanionic vesicles from ion pair amphiphile with double-chained cationic surfactant,” Colloid and Polymer Science, 292, 3, 589-597, 2014.
    Yamauchi, M.; Tsutsumi, K.; Abe , M.; Uosaki, Y.; Nakakura, M.; Aoki, N., “Release of drugs from liposomes varies with particle size,” Biol. Pharm.
    Bull., 30, 5, 963-966, 2007.
    Yang, Y. M., Wu, K. C., Huang, Z. L. and Chang, C. H., “On the stability of liposomes and catansomes in aqueous alcohol solutions,” Langmuir, 24, 5, 1695-1700, 2008.
    Yokouchi, Y., Tsunoda, T., Imura, T., Yamauchi, H., Yokoyama, S., Sakai, H. and Abe, M., “Effect of adsorption of bovine serum albumin on liposomal membrane characteristics,” Colloids and Surfaces Biointerfaces, 20, 2, 95-103, 2001.
    Yokoyama, S., Inagaki, A., Imura, T., Ohkubo, T., Tsubaki, N., Sakai, H. and Abe, M., “Membrane properties of cationic liposomes composed of dipalmitoylphosphatidylcholine and dipalmityldimethylammonium bromide,” Colloids and Surfaces Biointerfaces, 44, 4, 204-210, 2005.
    Zhang, X. R., Huang, J. B., Mao, M., Tang, S. H. and Zhu, B. Y., “From precipitation to vesicles: a study on self-organized assemblies by alkylammonium and its mixtures in polar solvents,” Colloid and Polymer Science, 279, 12, 1245-1249, 2001.
    Zheng, Z., Zhou, M., Qiao, W. and Luo, L., “Spontaneous vesicle formation in mixtures of quaternary ammonium compounds with carbamate and sodium dodecylbenzene sulfonate,” Journal of Surfactants and Detergents, 18, 1, 171-178, 2015.
    Zuidam, N. J. and Barenholz, Y., “Electrostatic parameters of cationic liposomes commonly used for gene delivery as determined by 4-heptadecyl-7-hydroxycoumarin,” Biochimica et Biophysica Acta - Biomembranes, 1329, 2, 211-222, 1997.
    王鈺婷,“帶負電陰陽離子液胞的物化特性及維他命E醋酸酯包覆效率—離子對雙親分子碳鏈結構的影響,”國立成功大學化學工程學系碩士論文,2015。
    吳芷容,“利用帶正電的陰陽離子液胞做為DNA載體之可行性的研究,”國立成功大學化學工程學系碩士論文,2008。
    呂奇達,“帶正電的陰陽離子液胞與DNA之結合行為的探討,”國立成功大學化學工程學系碩士論文,2005。
    李佩蓁,“液胞組成分子的碳鏈長度對於含膽固醇之帶正電陰陽離子液胞物理特性的影響,”國立成功大學化學工程學系碩士論文,2014。
    李家如,“含不對稱碳鏈離子對雙親分子及帶負電脂質之陰陽離子液胞的物理穩定性及維他命E醋酸酯包覆效率,”國立成功大學化學工程學系碩士論文,2011。
    李承軒,“帶正電陰陽離子液胞及其與DNA形成之複合物的物理穩定性,”國立成功大學化學工程學系博士論文, 2015.
    林冠豪,“帶電的陰陽離子液胞之製備及物理穩定性研究,”國立成功大學化學工程學系碩士論文,2004。
    洪振益,“溫度效應對帶電陰陽離子液胞釋放行為的影響,”國立成功大學化學工程學系碩士論文,2009。
    徐立銘,“陰陽離子液胞包覆行為之探討,”國立成功大學化學工程學系碩士論文,2002。
    張家綺,“以碳鏈長度為16-16-12之三碳鏈離子對雙親分子製備之陰陽離子液胞的物理特性,”國立成功大學化學工程學系碩士論文,2016。
    張維芬,“添加劑對雙十六碳鏈離子對雙親分子形成之陰陽離子液胞物化特性的影響,”國立成功大學化學工程學系碩士論文,2012。
    張維瀚,“添加劑對於陰陽離子雙層膜之相轉移行為的探討,”國立成功大學化學工程學系碩士論文,2012。
    陳振豪,“不對稱碳鏈對離子對雙親分子雙層膜結構性質之影響以及環糊精/聚胺酸雙親分子凝膠化機制之探討,”國立成功大學化學工程學系碩士論文,2016。
    廖怡芬,“長碳鏈醇類添加劑對帶電陰陽離子液胞物理穩定性的影響,”國立成功大學化學工程學系碩士論文,2006。
    陳孟真,“膽固醇的添加對於碳鏈長度為16-16-12之三碳鏈離子對雙親分子Langmuir單分子層行為的影響,”國立成功大學化學工程學系碩士論文,2017。
    蘇于晴,“具三條十六碳鏈之離子對雙親分子形成的陰陽離子液胞物理性質及液胞雙層膜中分子排列特性:膽固醇效應,”國立成功大學化學工程學系碩士論文, 2017.
    蘇珮瑄,“類三碳鏈離子對雙親分子/膽固醇混合系統形成之陰陽離子液胞的特性分析,”國立成功大學化學工程學系碩士論文, 2018.

    下載圖示 校內:2024-07-01公開
    校外:2024-07-07公開
    QR CODE