本研究先分別將陰離子型界面活性劑十二烷基硫酸鈉與陽離子型界面活性劑十二烷基三甲基溴化銨、十四烷基三甲基溴化銨及十六烷基三甲基溴化銨的溶液混合，形成三種離子對雙親分子（ion pair amphiphile, IPA），再透過適當的製程設計製備出具有適當穩定性及特殊電性的陰陽離子液胞（catanionic vesicle）。

　　粒徑分布及界面電位的量測顯示在IPA薄膜的水合過程中，若在水相中添加與IPA組成分子相同的單鏈陰離子型或陽離子型界面活性劑，可形成帶電陰陽離子液胞。實驗結果顯示，相對於IPA含量而言，當添加過量的單鏈界面活性劑時，通常會形成液胞與微胞共存的混合系統。然而當單鏈界面活性劑的添加量相對較低時，則易產生穩定性較佳的液胞結構。此外，由所生成液胞的界面電位分析結果，並無法完全說明液胞的穩定性，顯示液胞雙層結構的組成在液胞穩定性上扮演著重要的角色。

　　Ion pair amphiphiles (IPAs), obtained by mixing aqueous solutions of anionic and cationic surfactants, were made of an anionic surfactant, sodium dodecylsulfate, and three cationic surfactants, dodecyltrimethylammonium bromide, tetradecyltrimethylammonium bromide, and hexadecyltrimethyl- ammonium bromide. The IPAs were then used by a proper process to obtain catanionic vesicles with specific charge characteristics.

　　The particle size and zeta potential measurements indicated that by adding the single-chain anionic or cationic surfactants, the component of the IPA, in the aqueous phase during the hydration of the IPA film in the process, one was able to obtain charged catanionic vesicles. The experimental results demonstrated that in comparison with the IPA amount, when excess single-chain surfactant was added, a mixed system containing vesicles and micelles was usually formed. However, when excess IPA was available, it was easy to form vesicles with higher stability. Moreover, since the vesicle stability could not be solely explained by the zeta potential data, the bilayer composition of the vesicles appeared to play an important role in the vesicle stability.

Almgren, M., “Mixed micelles and other structures in the solubilization of bilayer lipid membranes by surfactants.” Biochimica et Biophysica Acta, 1508, 146-163, 2000.

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,” J. Org. Chem., 63, 7640-7651, 1998.

Bhattacharya, S. and De, S., “Vesicle formation from dimeric ion-pair amphiphiles. Control over vesicular thermotropic and ion-transport properties as a function of intra-amphiphilic headgroup separation,” Langmuir, 15, 3400-3410, 1999.

Bhattatcharya, S. and Haldar, S., “Interaction between cholesterol and lipids in bilayer membranes. Role of lipid headgroup and hydrocarbon chain-backbone linkage, Biochimica et Biophysica Acta, 1467, 39-53, 2000.

Blanzat, M., Perez, E., Rico-lattes, I. and Lattes, A., “Synthesis and anti-HIV activity of catanionic analogs of galactosyceramide,” New J. Chem., 23, 1063-1065, 1999.

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.
Borochov, “Phase behavior of mixtures of cholesterol and saturated phosphatidylglycerols,” Chemistry and Physics of lipids, 76, 85-92, 1995.

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.

Bucak, S., Robinson, B.H., Fontana, A., “Kinetics of induced vesicle breakdown for cationic and catanionic systems,” Langmuir, 18, 22, 8288-8294, 2002.
Caillet, C., Hebrant, M. and Tondre, C., “Sodium octyl sulfate / cetyltrimethylammonium bromide catanionic vesicles: aggregate composition and probe encapsulation,” Langmuir, 16(23), 9099-9102, 2000.

Carrion, F.J., Maza, A.D., Parra, J.L., “The influence of ionic strength and lipid bilayer charge on the stability of liposomes,” Journal of Colloid and Interface Science, 164, 78-87, 1994.

Casals, E., Galan, A.M., Escolar, G., Gallardo, M. and Estelrich, J., “Physical stability of liposomes bearing hemostatic activity,” Chemistry and Physics of Lipids, 125(2), 139-146, 2003.

Chien, C.-L., Yeh, S.-J., Yang, Y.-M., Chang, C.-H., and Maa, J.-R., “Formation and Encapsulation of Catanionic Vesicles,” J. Chin. Colloid and Interface Soc., 24, 31-45, 2002.

Chiruvolu, S., Israelachvili, J.N., Naranjo, E., Xu, Z., and Zasadzinski, J.A., “Measurement of forces between spontaneous vesicle-forming bilayers,” Langmuir, 11(11), 4256-4266, 1995.

Chung, Y.-C., Lee, H.-J., and Park, J.-Y., “Bilayer properties of the multiple-chain ion pair amphiphiles,” Bull. Korean Chem. Soc., 19, 11, 1249-1252, 1998.

Chung, Y.-C. and Lee, H.-J., “Ion-sensing property of an ion pair amphiphile,” Bull. Korean Chem. Soc., 20, 1, 16-18, 1999.

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., Chung, Y.-C., Chun, B.-C., “Highly pH-sensitive ion pair amphiphile vesicle,” Colloids and Surfaces B : Biointerfaces, 29, 75-80, 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.

Deo N. and Somasumdaran, P., “Mechanism of mixed liposome solubilization in the presence of sodium dodecyl sulfate,” Colloids and Surfaces A : Physicochemical and Engineering Aspects, 186, 33-41, 2001.

Dias, R.S., Lindman, B. and Miguel, M.G., “DNA interaction with catanionic vesicles,” the Journal of Physical Chemistry B, 106, 12600-12607, 2002.

Dias, R.S., LIndman, B. and Miguel, M.G., “Compaction and decompaction of DNA in the presence of catanionic amphiphile mixture,” the Journal of Physical Chemistry B, 106, 12608-12612, 2002.

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, 163-168, 2002.

Fukuda, H., Kawata, K. and Okuda, H., “Bilayer-forming ion-pair amphiphiles from single-chain surfactants,” J. Am. Chem. Soc., 112, 1635-1637, 1990.

Gao, X. and Huang, L., “Cationic liposome-mediated gene transfer,” Gene therapy, 2, 710-722, 1995.

Hammond, K., Reboiras, M.D., Lyle, I.G., and Jones, M.N., “Characterisation of phosphatidylcholine / phosphatidylinositol sonicated vesicles : effects of phospholipid composition on vesicle size,” Biochimica et Biophysica Acta, 774, 19-25, 1984.

Hao, J., Wang, J., Liu, W., Abdel-Rahem, R. and Hoffmann, G., “Zn2+ - induced vesicle formation,” J. Phys. Chem. B, 108, 1168-1172, 2004.

Herrington, K. L. and Kaler, E. W., “Phase behavior of aqueous mixtures of dodecyltrimethylammonium bromide (DTAB) and sodium dodecyl sulfate (SDS),” J. Phys. Chem. 97, 13792-13802, 1993.

Hirano k., Fukuda, H., “Polymerizable ion-paired amphiphiles” Langmuir, 7, 6, 1045-1047, 1991.

Holmberg, K., “Handbook of applied surface and colloid chemistry,” John Wiley and Sons, 2001.

Israelachvili, J. N., Mitchell, D. J. and Ninham, B. W., “Theory of self-assembly of hydrocarbon amphiphiles into micelles and bilayers,” J. Chem. Soc. Faraday Trans. 72, 1525, 1976.

Jokela, P., Jönsson, B., and Khan, A., “Phase equilibria of catanionic surfactant-water systems,” the Journal of Physical Chemistry, 91, 3291-3298, 1987.

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.

Kaler, E. W., Herrington, K. L. and Murthy, A. K., “Phase behavior and structures of mixtures of anionic and cationic surfactants,” J. Phys. Chem. 96, 6698-6707, 1992.

Kondo, Y., Abe, Masahiko, Ogino, K., Uchiyama, H., Tucker, E.E., Scamehorn, J.F., Christian, S.D., “Stability of surfactant vesicles formed cationic didodecyldimethylammonium bromide,” Colloids and Surfaces B : Biointerfaces, 1 , 51-56, 1993.

Lasic, D.D., “Liposomes :from physics to applications” Elsevier : New York, 1993.

Lasic, D.D., “Liposomes in gene delivery,” CRC Press : Boca Raton, 1997.
Maitani, Y., Nakagaki, M., Nagai, T., “Surface potential of liposomes with entrapped insulin,” International Journal of Pharmaceutics, 64, 89-98, 1990.

Marques, E.F., Regev, O., Khan, A., Lindman, B., “Self-organization of double-chained and pseudodouble-chained surfactants : counterion and geometry effects,” Advances in Colloid and Interface Science, 100-102, 83-104, 2003.

McCullough, H. N. and Juliano, R.L., “Organ-selective action of an antitumor drug: pharmacologic studies of liposome encapsulated cytosine arabinoside administered via the respiratory system of the rat,” J. Natl. Cancer Inst., 63, 727, 1979.

Menger, F.M., Binder, W.H., and Keiper, J.S., “Cationic surfactants with counterions of glucuronate glycosides,” Langmuir, 13, 3247-3250, 1997.

Miguel, M.G., Pais, A.A.C.C., Dias, R.S., Leal, C., Rosa, M. and Lindman, B., “DNA-cationic amphiphile interactions,” Colloids and Surfaces A: Physicochem. Eng. Aspects 228, 43-55, 2003.

Morgan, J.D., Johnson, C.A., Kaler, E.W., ”Polymerization of equilibrium vesicles,” Langmuir, 13, 6447-6451, 1997.

New, R.R.C., “in Liposomes : a practical approach” Oxford University Press : New York, 1990.

Plessis, J.D., Ramachamdran, C., Weiner, N., Muller, D.G., “The influence of lipid composition and lamellarity of liposomes on the physical stability of liposomes up storage,” International Journal of Pharmaceutics, 127, 273-278, 1996.

Purohit, G., Sakthivel, T. and Florence A.T., “Interaction of cationic partial dendrimers with charged and neutral liposomes,” International Journal of Pharmaceutics, 214, 71-76, 2001.

Safran, S.A., Pincus, P.A., Amdelman, D. and MacKintosh, F.C., “Stability and phase behavior of mixed surfactant vesicles,” the American Physical Society, 43, 2, 1071-1078, 1991.

Sekiguchi, A., Yamauchi, H., Manosroi, A., “Molecular interactions between phospholipids and glycolipids in a lipid bilayer,” Colloids and Surfaces B: Biointerfaces, 4, 287-296, 1995.

Tondre, C., 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.

Walker S.A., and Zasadzinski, A.J., “Electrostatic control of spontaneous vesicle aggregation,” Langmuir, 13(19), 5076-5081, 1997.

Yoshida, A., Manosroi, A., Manosroi, J., Yamauchi, H. and Abe., M., “Molecular interactions between phospholipid and mangostin in a lipid bilayer.” Colloids and Surfaces B : Biointerfaces, 4, 423-432, 1995.

Yuet, P.K. and Blankschtein, D., “Molecular-thermodynamic modeling of mixed cationic / anionic vesicles,” Langmuir, 12(16), 3802-3818, 1996.

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。

李雅鈺, “含膽固醇之陰陽離子液胞穩定性及包覆行為的研究,” 國立成功大學化學工程學系碩士論文, 2004。

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。

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。

鐘依玲, “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。