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論文名稱(外文):The Effects of Additives on the Physicochemical Properties of Catanionic Vesicles Formed by Dihexdecyl-Chained Ion Pair Amphiphile
指導教授(外文):Chien-Hsiang Chang
外文關鍵詞:catanionic vesicleion pair amphiphilevesiclevesicular bilayer
  • 被引用被引用:6
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本研究藉由提高溫度增加離子型界面活性劑在水中的溶解度,並利用沉澱方法製備出雙十六碳鏈離子對雙親分子(ion pair amphiphile, IPA)hexadecyltrimethylammonium-hexadecylsulfate (HTMA-HS)。然後添加不同莫耳分率的膽固醇及雙十六碳磷酸鹽(dihexadecyl phosphate, DHDP),以強制性製程由HTMA-HS製備出陰陽離子液胞 (catanionic vesicle),並探討添加劑對HTMA-HS所形成之液胞物化性質的影響。此外,與利用其他兩種碳鏈長度不同之IPA所製備出的陰陽離子液胞比較,分析IPA碳鏈長度及對稱性對陰陽離子液胞物化性質的影響。
分析不同IPA添加膽固醇後所形成之陰陽離子液胞的物化特性,發現IPA碳鏈長度越長,所形成之液胞的界面電位越大,此現象可能是HTMA-HS所形成之液胞比其他兩種IPA所形成之液胞有較佳物理穩定性的原因。然而碳鏈較短且對稱之IPA (DTMA-DS)的疏水碳鏈與膽固醇的作用較佳,並有良好之結構上的配位,因此添加少量的膽固醇即可明顯提升其液胞之物理穩定性。

In this study, the surfactant solubility in water was increased by rasimg the temperature and the ion pair amphiphile (IPA) hexadecyltrimethylammonium-hexadecylsulfate (HTMA-HS) was prepared by a precipitation approach. Then the catanionic vesicles were fabricated from HTMA-HS with the addition of different molar fractions of cholesterol and dihexadecyl phosphate (DHDP) by a force formation process, and the effects of additives on the physicochemical properties of the catanionic vesicles composed of HTMA-HS were investigated. In addition, the effects of alkyl chain length and symmetry of IPA on the physicochemical properties of catanionic vesicles were analyzed by comparing the catanionic vesicles composed of HTMA-HS with those composed of two other IPAs with different chain lengths.
  The experimental results indicated that catanionic vesicles which were stable up to 50 days could be prepared from HTMA-HS. However, significant aggregation between the vesicles was detected. The addition of a proper amount of cholesterol or DHDP could slow down the aggregation or fusion rates of the vesicles, but defects in the vesicular bilayer structures might be induced, resulting in limited enhancement effect on the physical stability of the catanionic vesicles. By adding both cholesterol and DHDP, the mechanical strength of the vesicular bilayers and the electrostatic repulsion between the vesicles were increased, and the physical stability of the catanionic vesicles could be significantly improved. The arrangement of molecular alkyl chains in the vesicular bilayers was analyzed by the infrared spectroscopy, and it was found that the molecular alkyl chains became less ordered when cholesterol was added below the phase transition temperature of the HTMA-HS bilayers. The addition of DHDP only slightly lowered the order of the molecular alkyl chains.
  By analyzing the physicochemical characteristics of the catanionic vesicles composed of different IPAs with the addition of cholesterol, one could find that the longer the alkyl chain length of IPA, the more positive the zeta potential of catanionic vesicles. This might be the reason for the vesicles composed of HTMA-HS possessing better physical stability than the vesicles composed of two other IPAs. However, the IPA (DTMA-DS) with shorter and symmetric alkyl chains could better interact and match well in structure with cholesterol. As a result, adding a small amount of cholesterol could significantly enhance the physical stability of the vesicles composed of DTMA-DS.

摘要 I
Abstract III
誌謝 V
目錄 VI
表目錄 IX
圖目錄 XI
符號說明 XV
第一章 緒論 1
1-1 前言 1
1-2 研究動機與目的 3
1-3 文獻回顧 3
1-3-1 離子對雙親分子 3
1-3-2 帶電液胞 5
1-3-3 膽固醇的效應 6
1-3-4 液胞雙層膜中分子碳氫鏈的排列 8
1-3-5 陰陽離子界面活性劑之碳鏈對稱性和長度的效應 9
第二章 實驗 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 24
2-2-4 傅利葉轉換紅外光譜儀 25
2-2-5 穿透式電子顯微鏡 26
2-3 實驗方法 27
2-3-1 HTMA-HS的製備 27
2-3-2 液胞分散液的製備 28
2-3-3 粒徑分布及界面電位的量測 29
2-3-4 穿透式紅外光光譜的分析 29
第三章 結果與討論 39
3-1 離子對雙親分子 39
3-2 陰陽離子液胞的合成 41
3-2-1 HTMA-HS形成之陰陽離子液胞 41
3-2-2 帶負電之陰陽離子液胞 42
3-2-3 膽固醇的影響 44
3-2-4 含膽固醇之帶負電陰陽離子液胞 47
3-2-5 液胞雙層膜之相轉移溫度 50
3-3 陰陽離子界面活性劑碳鏈長度與對稱性的影響 51
3-3-1 物理穩定性 51
3-3-2 界面電位 54
3-3-3 粒徑 54
3-3-4 雙層膜的排列 56
第四章 結論 95
參考文獻 97

Ahmad, I., Longenecker, M. Samuel, J., and Allen, T. M., “Antibody-targeted delivery of doxorubicin entrapped in sterically in sterically stabilized liposomes can eradicate lung cancer in mice, Cancer Research 55,1484-1487, 1993.
Almeida, P. F., “A simple thermodynamic model of the liquid-ordered state and the interactions between phospholipids and cholesterol, Biophysical Journal 100, 420-429, 2011.
Ang, C. A., “含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。
Bach, D., and Wachtel, E., “Phospholipid/cholesterol model membranes: formation of cholesterol crystallites, Biochimica et Biophysica Acta 1610, 187-197, 2003.
Bhattacharya, S., De, S., 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, 7640-7651, 1998.
Bhattacharya, S., and Haldar, J., “Interactions between cholesterol and lipids in bilayer membranes. Role of lipid headgroup and hydrocarbon chain-backbone linkage, Biochimica et Biophysica Acta 1467, 39-53, 2000.
Bhattacharya, S., and Haldar, S., “Molecular design of surfactants to tailor its aggregation properties, Colloids and Surfaces A: Physicochem. Eng. Aspects 205, 119-126, 2002.
Blanzat, M., Perez, E., Rico-Latters, R., 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(galβ1cer), Langmuir 15, 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, 4267-4277, 1995.
Campbell, R. B., Balasubramanian, S. V., and Straubinger, R. M., “Phospholipid-cationic lipid interactions: influences on membrane and vesicle properties, Biochimica et Biophysica Acta 1512, 27-39, 2001.
Chiruvolu, S., ; Israelachvili, J. N., ; Naranjo, E., Xu, Z., and Zasadzinski, J. A., “ Measurement of forces between spontaneous vesicle-forming bilayers, Langmuir 11, 4256-4266, 1995.
Chou, T.-H., and Chang, C.-H., “Thermodynamic characteristics of mixed DPPC/DHDP monolayers on water and phosphate buffer subphases, Langmuir 16, 3385-3390, 2000.
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, 111-121, 2002.
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, 83-93, 2003.
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, 179-184, 2004.
Dhanikula , A. B., and Panchagnula, R., “Fluorescence anisotropy, FT-IR spectroscopy and 31-P NMR studies on the interaction of paclitaxel with lipid bilayers, Lipids 43, 569-579, 2008.
Eisenberg, M., Gresalfi, T., Riccio, T., McLaughlin, S., “Adsorption of monovalent cations to bilayer membranes containing negative phospholipids, Biochemistry18, 5213–5223, 1979.
Fatouros, D. G., and Antimisiaris, S. G., “Effect of amphiphilic drugs on the stability and zeta-potential of their liposome formulations: A study with prednisolone, diazepam, and griseofulvin, Journal of Colloid and Interface Science 251, 271-277, 2002.
Fukuda, H., Kawata, K., and Okuda, H., “Bilayer-forming ion-pair amphiphiles from single-chain surfactants, Journal of the American Chemical Society 112, 1635-1637, 1990.
Fuller, G. F., and Shields, D., “Molecular basis of medical cell biology, McGraw-Hill, New York, 1998.
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。
Herrington, K. L., Kaler, E. W., Miller, D. D., Zasadzinski, J. A., and Shivkumar, C., “Phase-behavior of aqueous mixtures of dodecyltrimethylammonium bromide (DTAB) and sodium dodecyl-sulfate (SDS), Journal of Physical Chemistry 97,13792-13802, 1993.
Hirano K., and Fukuda, H., “Polymerizable ion-paired amphiphiles, Langmuir 7, 1045-1047, 1991.
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, 15-25, 1976.
Kaler, E. W., Murthy, A. K., Rodriguez, B. E., and Zasadzinski, A. N., “Spontaneous vesicle formation in aqueous mixtures of single-tailed surfactants, Science 245, 1371-1374, 1989.
Kodati, V. R., and Lafleur, M., “Comparison between orientational and conformational orders in fluid lipid bilayers, Biophysical Journal 64, 163-170, 1993.
Lasic, D. D., “Liposomes: from physics to applications, Elsevier, New York, 265-318, 1993.
Lasic, D. D., “Liposomes in gene delivery, CRC Press, New York, 67-112, 1997.
Lewis, R. N.A.H., and McElhaney, R. N., “The structure and organization of phospholipid bilayers as revealed by infrared spectroscopy, Chemistry and Physics of Lipids 96, 9-21, 1998.
Mannock, D. A., Lewis, R., McMullen, T. P. W., and McElhaney, R. N., “The effect of variations in phospholipid and sterol structure on the nature of lipid-sterol interactions in lipid bilayer model membranes, Chemistry and Physics of Lipids 163, 403-448, 2010.
Marsh, D., “Liquid-ordered phases induced by cholesterol: A compendium of binary phase diagrams. Biochimica et Biophysica Acta-Biomembranes 1798, 688-699, 2010.
McIntosh, T. J., Magid, A. D., and Simon, S. A., “Cholesterol modifies the short-range repulsive interactions between phosphatidylcholine membrances, Biochemistry 28, 17-25, 1989.
McMullen, T. P. W., Lewis, N. A. H., 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, 516-522, 1993.
McMullen, T. P. W., Lewis, R. N. A. H., 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, 2056-2065, 2000.
Menger, F. M., Binder, W. H., and Keiper, J. S., “Cationic surfactants with counterions of glucuronate glycosides, Langmuir 13, 3247-3250, 1997.
Michel, N., Fabiano, AS., Polidori, A., and Jack, R., “Determination of phase transition temperatures of lipids by light scattering, Chemistry and Physics of Lipids139, 1-19, 2006.
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, 106-113, 2005.
Regev, O., and Khan, A., “Alkyl chain symmetry effects in mixed cationic-anionic surfactant systems, Journal of Colloid and Interface Science 182, 95-109, 1996 .
Segota, S., and Tezak, D., “Spontaneous formation of vesicles, Advances in Colloid and Interface Science 121, 51-75, 2006.
Soussan, E., Cassel, S., Blanzat, M., and Rico-Lattes, I., “Drug delivery by soft matter : matrix and vesicular carriers, Angewandte Chemie-International Edition 48, 274-288, 2009.
Teixeira, C. V., Blanzat, M., Koetz, J., Rico-Lattes, I., and Brezesinski, G., “In-plane miscibility and mixed bilayer microstructure in mixtures of catanionic glycolipids and zwitterionic phospholipids, Biochimica et Biophysica Acta 1758, 1797-1808, 2006.
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, 115-134, 2001.
Vist M. R., and Davis J, H., “Phase equilibria of cholesterol/ dipalmitoylphosphatidylcholine mixtures: H-2 Nuclear magnetic resonance and differential scanning calorimetry, Biochemistry 29, 451-464, 1990.
Walker, S. A., and Zasadzinski, A. J., “Electrostatic control of spontaneous vesicle aggregation, Langmuir 13, 5076-5081, 1997.
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, 1695-1700, 2008.
Yatcilla, MT., Herrington, KL., Brasher, LL., Kaler, EW., Chiruvolu, S., and Zasadzinski, JA., “Phase behavior of aqueous mixtures of cetyltrimethylammonium bromide (CTAB) and sodium octyl sulfate (SOS), Journal of Physical Chemistry 100, 5874-5879, 1996.
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 B-Biointerfaces 20, 95-103, 2001.
王偉丞,“DPPC/DHDP混合微脂粒的物理穩定性之研究, 國立成功大學化學工程學系碩士論文,2001。
李威漢,“陰陽離子界面活性劑的製備及其相轉移行為的熱卡分析, 國立成功大學化學工程學系碩士論文,2010。
李雅鈺,“含膽固醇之陰陽離子液胞穩定性及包覆行為之研究, 國立成功大學化學工程學系碩士論文,2004。
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。
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學系碩士論文,2002。
陳柏瑋,“白蛋白存在下帶正電陰陽離子液胞穩定性的探討, 國立成功大學化學工程學系碩士論文,2007。
游文月,“共溶劑促進陰陽離子液胞自發性形成之研究, 國立成功大學化學工程學系碩士論文,2004。
黃鉦琳,“帶電陰陽離子液胞的形成及其膠化之研究, 國立成功大學化學工程學系碩士論文,2007。
葉紹任,“共溶劑對陰陽離子液胞穩定性的影響, 國立成功大學化學工程學系碩士論文,2003。
鍾依玲,“陰/陽離子液胞自發性形成之探討, 國立成功大學化學工程學系碩士論文,2002。
簡振龍,“陰/陽離子界面活性劑的混合增效作用之研究, 國立成功大學化學工程學系碩士論文,2000。

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