Modified and derived ethanol injection toward liposomes: development of the process

References

• Abécassis, B., Testard, F., Arleth, L., Hansen, S., Grillo, I., Zemb, T. (2007). Electrostastic control of spontaneous curvature in catanionic reverse micelles. Langmuir 23:9983–9989.
   PubMedGoogle Scholar
• Athmakuri, K., Padala, C., Litt, J., Cole, R., Kumar, S., Kane, R. S. (2010). Controlling DNA adsorption and diffusion on lipid bilayers by the formation of lipid domains. Langmuir 26:397–401.
   PubMedGoogle Scholar
• Bangham, A. D., Standish, M. M., Watkins, J. C. (1965). Diffusion of univalent ions across the lamellae of swollen phospholipids. J Mol Biol 13:238–252.
   PubMed Web of Science ®Google Scholar
• Batzri, S., Korn, E. D. (1973). Single bilayer liposomes prepared without sonication. Biochim Biophys Acta 298:1015–1019.
   PubMed Web of Science ®Google Scholar
• Bergström, L. M. (2001). Thermodynamics of unilamellar vesicles: influence of mixing on the curvature free energy of a vesicle bilayer. J Colloid Interface Sci 240:294–306.
   PubMedGoogle Scholar
• Boffi, F., Bonincontro, A., Bordi, F., Bultrini, E., Cametti, C., Congiu-Castellano, A., et al. (2002). Two-step mechanism in cationic lipoplex formation as observed by dynamic light scattering, dielectric relaxation, and circular dichroism methods. Phys Chem Chem Phys 4:2708–2713.
   Web of Science ®Google Scholar
• Camli, S. T., Buyukserin, F., Balci, O., Budak, G. G. (2010). Size controlled synthesis of sub-100 nm monodisperse poly(methylmethacrylate) nanoparticles using surfactant-free emulsion polymerization. J Colloid Interface Sci 344:528–532.
   PubMed Web of Science ®Google Scholar
• Chanturiya, A., Leikina, E., Zimmerberg, J., Chernomordik, L. V. (1999). Short-chain alcohols promote an early stage of membrane hemifusion. Biophys J 77:2035–2045.
   PubMed Web of Science ®Google Scholar
• Dancey, G. F., Yasuda, T., Kinsky, S. C. (1978). Effect of liposomal model membrane composition on immunogenicity. J Immunol 120:1109–1113.
   PubMed Web of Science ®Google Scholar
• Dos Santos, N., Cox, K. A., McKenzie, C. A., van Baarda, F., Gallagher, R. C., Karlsson, G., et al. (2004). pH gradient loading of anthracyclines into cholesterol-free liposomes: enhancing drug loading rates through use of ethanol. Biochim Biophys Acta 1661:47–60.
   PubMed Web of Science ®Google Scholar
• Galarneau, A., Sartori, F., Cangiotti, M., Mineva, T., Di Renzo, F., Ottaviani, M. F. (2010). Sponge mesoporous silica formation using disordered phospholipid bilayers as template. J Phys Chem B 114:2140–2152.
   PubMed Web of Science ®Google Scholar
• Garti, N., Yaghmur, A., Leser, M. E., Clement, V., Watzke, H. J. (2001). Improved oil solubilization in oil/water food grade microemulsions in the presence of polyols and ethanol. J Agric Food Chem 49:2552–2562.
   PubMed Web of Science ®Google Scholar
• Gentine, P., Bubel, A., Crucifix, C., Bourel-Bonnet, L., Frisch, B. (2012). Manufacture of liposomes by isopropanol injection: characterization of the method. J Liposome Res 22:18–30.
   PubMed Web of Science ®Google Scholar
• Gurtovenko, A., Anwar, J. (2009). Interaction of ethanol with biological membranes: the formation of non-bilayer structures within the membrane interior and their significance. J Phys Chem B 113:1983–1992.
   PubMedGoogle Scholar
• Helfrich, W. (1973). Elastic properties of lipid bilayers: theory and possible experiments. Z Naturforsch 28:693–703.
   Google Scholar
• Justo, O. R., Moraes, A. M. (2011). Analysis of process parameters on the characteristics of liposomes prepared by ethanol injection with a view to process scale-up: effect of temperature and batch volume. Chem Eng Res Des 89:785–792.
   Web of Science ®Google Scholar
• Kim, J. Y., Kim, J. K., Park, J. S., Byun, Y., Kim, C. K. (2009). The use of PEGylated liposomes to prolong circulation lifetimes of tissue plasminogen activator. Biomaterials 30:5751–5756.
   PubMed Web of Science ®Google Scholar
• Komatsu, H., Bouma, B., Wirtz, K. W., Taraschi, T. F., Janes, N. (2000). Activity of phosphatidylinositol transfer protein is sensitive to ethanol and membrane curvature. Biochem J 348:667–673.
   PubMedGoogle Scholar
• Kremer, J. M., Esker, M. W., Pathmamanoharan, C., Wiersema, P. H. (1977). Vesicles of variable diameter prepared by a modified injection method. Biochemistry 16:3932–3935.
   PubMed Web of Science ®Google Scholar
• Lasic, D. D., Joannic, R., Keller, B. C., Frederik, P. M., Auvray, L. (2001). Spontaneous vesiculation. Adv Colloid Interface Sci 89–90:337–349.
   Google Scholar
• Leng, J., Egelhaaf S. U., Cates, M. E. (2002). Kinetic pathway of spontaneous vesicle formation. Europhys Lett 59:311–317.
   Google Scholar
• Leng, J., Egelhaaf, S. U., Cates, M. E. (2003). Kinetics of the micelle-to-vesicle transition: aqueous lecithin-bile salt mixtures. Biophys J 85:1624–1646.
   PubMed Web of Science ®Google Scholar
• Lindman, B., Alexandridis, P. (2000). Amphiphilic molecules: small and large. In: Lindman, B., Alexandridis, P., (Eds.), Amphiphilic block copolymers: self-assembly and applications ( pp. 1–12). Amsterdam: Elsevier Science B.V.
   Google Scholar
• Maitani, Y., Soeda, H., Junping, W., Takayama, K. (2001). Modified ethanol injection method for liposomes containing β-sitosterol β-D-glucoside. J Liposome Res 11:115–125.
   PubMed Web of Science ®Google Scholar
• Meure, L. A., Foster, N. R., Dehghani, F. (2008). Conventional and dense gas techniques for the production of liposomes: a review. AAPS Pharm Sci Tech 9:798–809.
   PubMed Web of Science ®Google Scholar
• Monneraye, J. (2004). Transparency in vesicle-based formulations. Le MiDiFABs 2:17–24.
   Google Scholar
• Pabst, G., Rappolt, M., Amenitsch, H., Bernstorff, S., Laggner, P. (2000). X-ray kinematography of temperature-jump relaxation probes the elastic properties of fluid bilayers. Langmuir 16:8994–9001.
   Google Scholar
• Pabst, G., Katsaras, J., Raghunathan, V. A., Rappolt, M. (2003). Structure and interactions in the anomalous swelling regime of phospholipid bilayers. Langmuir 19:1716–1722.
   Web of Science ®Google Scholar
• Paunov, V. N., Sandler, S. I., Kaler, E. W. (2000). A simple molecular model for the spontaneous curvature and the bending constants of nonionic surfactant monolayers at the oil/water interface. Langmuir 16:8917–8925.
   Google Scholar
• Péroche, S., Degobert, G., Putaux, J. L., Blanchin, M. G., Fessi, H., Parrot-Lopez, H. (2005). Synthesis and characterisation of novel nanospheres made from amphiphilic perfluoroalkylthio-beta-cyclodextrins. Eur J Pharm Biopharm 60:123–131.
   PubMed Web of Science ®Google Scholar
• Pons, M., Foradada, M., Estelrich, J. (1993). Liposomes obtained by the ethanol injection method. Int J Pharm 95:51–56.
   Web of Science ®Google Scholar
• Risselada, H. J., Marrink, S. J. (2009). Curvature effects on lipid packing and dynamics in liposomes revealed by coarse grained molecular dynamics simulations. Phys Chem Chem Phys 11:2056–2067.
   PubMed Web of Science ®Google Scholar
• Rosenkrands, I., Agger, E. M., Olsen, A. W., Korsholm, K. S., Andersen, C. S., Jensen, K. T., et al. (2005). Cationic liposomes containing mycobacterial lipids: a new powerful Th1 adjuvant system. Infect Immun 73:5817–5826.
   PubMed Web of Science ®Google Scholar
• Sun, W. Q., Leopold, A. C., Crowe, L. M., Crowe, J. H. (1996). Stability of dry liposomes in sugar glasses. Biophys J 70:1769–1776.
   PubMed Web of Science ®Google Scholar
• Van Damme, P., Cramm, M., Safary, A., Vandepapelière, P., Meheus, A. (1992). Heat stability of a recombinant DNA hepatitis B vaccine. Vaccine 10:366–367.
   PubMed Web of Science ®Google Scholar
• Venditti, F., Angelico, R., Palazzo, G., Colafemmina, G., Ceglie, A., Lopez, F. (2007). Preparation of nanosize silica in reverse micelles: ethanol produced during TEOS hydrolysis affects the microemulsion structure. Langmuir 23:10063–10068.
   PubMedGoogle Scholar
• Vollmer, D., Strey, R. (1995). Latent heat of spontaneous-curvature-induced lamellar-to-microemulsion transitions. Europhys Lett 32:693–698.
   Google Scholar
• Vollmer, D., Vollmer, J. (2001). Bending free energy and spontaneous curvature for micelles and microemulsions with weak and strong surfactants. Eur Phys J E 4:153–159.
   Google Scholar
• Wagner, A., Vorauer-Uhl, K., Kreismayr, G., Katinger, H. (2002). The crossflow injection technique: an improvement of the ethanol injection method. J Liposome Res 12:259–270.
   PubMed Web of Science ®Google Scholar
• Wesley, J. F. (2003). Osmolality—a novel and sensitive tool for detection of tampering of beverages adulterated with ethanol, γ-butyrolactone, and 1,4-butanediol, and for detection of dilution-tampered Demerol syringes. Microgram J 1:8–17.
   Google Scholar
• Zook, J. M., Vreeland, W. N. (2010). Effects of temperature, acyl chain length, and flow-rate ratio on liposome formation and size in a microfluidic hydrodynamic focusing device. Soft Matter 6:1352–1360.
   Web of Science ®Google Scholar