Membranes, vesicles, and other supramolecular systems made from fluorinated amphiphiles

Handbook of Nonmedical Applications of Liposomes: Volume III: From Design to Microreactors

Volumn , Issue , 2018, Pages 97-141

  Riess, Jean G ^a   Frézard, Frédéric ^a   Greiner, Jacques ^a   Krafft, Marie Pierre ^a   Santaella, Catherine ^a   Vierling, Pierre ^a   Zarif, Leila ^a  

^a UNIVERSITÉ CÔTE D'AZUR   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85052178446     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1201/9781351072724     Document Type: Chapter

References (199)

1. Fendler, J. H., Membrane Mimetic Chemistry, Wiley-Interscience, New York, 1983.
2. Gregoriadis, G., Ed., Liposome Technology, Vols. I—III, 2nd ed., CRC Press, Boca Raton, FL, 1993.
3. Lasic D. D., Liposomes: From Physics to Applications, Elsevier, Amsterdam, 1993.
4. Bangham, A. D., Standish, M. M., and Watkins, J. C., Diffusion of univalent ions across the lamellae of swollen phospholipids, J. Mol. Biol.,13, 238, 1965.
5. Eibl, H., Phospholipids as functional constituents of biomembranes, Angew. Chem., Int. Ed. Engl.,23, 257, 1984.
6. Ringsdorf, H., Schlarb, B., and Venzmer, J., Molecular architecture and function of polymeric oriented systems: models for the study of organization, surface recognition, and dynamics of biomembranes, Angew. Chem., Int. Ed. Engl.,27, 113, 1988.
7. Kunitake, T., Synthetic bilayer membranes: molecular design, self-organization, and application, Angew. Chem., Int. Ed. Engl.,31, 709, 1992.
8. Fuhrhop, J. H. and Helfrich, W., Fluid and solid fibers made of lipid molecular bilayers, Chem. Rev.,93, 1565, 1993.
9. Kunitake, T., A totally synthetic bilayer membrane, J. Am. Chem. Soc.,99, 3860, 1977.
10. Tran, C. D., Klahn, P. L., Romero, A., and Fendler, J. H., Characterization of surfactant vesicles as potential membrane models. Effect of electrolytes, substrates, and fluorescence probes, J. Am. Chem. Soc.,100, 1622, 1978.
11. Gebicki, J. M. and Hicks, M., Ufasomes are stable particles surrounded by unsaturated fatty acid membranes, Nature, 243, 232, 1973.
12. Hargreaves, W. R. and Deamer, D. W., Liposomes from ionic, single-chain amphiphiles, Biochemistry,17,3759,1978.
13. Riess, J. G., Arien, C., Greiner, J., Le Blanc, M., Manfredi, A., Pace, S., Varescon, C., and Zarif, L., Design, synthesis and evaluation of fluorocarbons and surfactants for in vivo applications: new perfluoroalkylated polyhydroxylated surfactants, in Blood Substitutes, Chang, T. M. S. and Geyer, R. P., Dekker, New York, 1989, 421.
14. Riess, J. G. and Greiner, J., Perfluoroalkylated sugar derivatives as surfactants and co-surfactants for biomedical uses, in Carbohydrates as Organic Raw Materials II, Descotes, G., Ed., VCH, Weinheim, 1993, 209.
15. Greiner, J., Riess, J. G., and Vierling, P., Fluorinated surfactants intended for biomedical uses, in Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications, Filler, R., Kobayashi, Y„ and Yagupolskii, L. M., Eds., Elsevier, Amsterdam, 1993, 339.
16. Kissa, E., Fluorinated Surfactants. Synthesis, Properties, Applications, Marcel Dekker, New York, 1994.
17. Riess, J. G., Highly fluorinated systems for oxygen carriage, diagnosis and drug delivery, Colloids Surf., 84, 33, 1994
18. Riess, J. G., Fluorine in our arteries, New Chem.,19, 893, 1995.
19. Riess, J. G., Fluorinated vesicles, J. Drug Target., 2, 455, 1994
20. Riess, J. G., Introducing a new element — fluorine — into the liposomal membrane, J. Liposome Res.,5, 413, 1995.
21. Mukerjee, P. and Yang, A. Y. S., Nonideality of mixing micelles of fluorocarbon and hydrocarbon surfactants and evidence of partial miscibility from differential conductance data, J. Phys. Chem.,80, 1388, 1976.
22. Funasaki, N. and Hada, S., Existence of critical demicellization concentration, J. Colloid Interface Sei.,73, 425, 1980.
23. Mysels, K. J., Critical demicellization concentration?, J. Colloid Interface Sei.,66, 331, 1978.
24. Asakawa, T., Miyagishi, S., and Nishida, M., Coexistence of two kinds of mixed micelles revealed by gel filtration, Langmuir,3, 821, 1987.
25. Kunitake, T., Tawaki, S. I., and Nakashima, N., Excimer formation and phase separation of hydrocarbon and fluorocarbon bilayer membranes, Bull. Chem. Soc. Jpn.,56, 3235, 1983.
26. Kunitake, T. and Higashl, N., Bilayer membranes of fluorocarbon amphiphiles, Makramol, Chem., Suppl.,14,81,1985.
27. Elbert, R., Folda, T., and Ringsdorf, H., Saturated and polymerizable amphiphiles with fluorocarbon chains. Investigation in monolayers and liposomes, J. Am. Chem. Soc.,106, 7687, 1984.
28. Overney, R. M., Meyer, E., Frommer, J., Brodbeck, D., Liithi, R., Howald, L., Giintherodt, H. J., Fujlhira, M Takano, H., and Gotoh, Y., Friction measurements on phase-separated thin films with a modified atomic force microscope, Nature,359, 133, 1992.
29. Ishikawa, Y., Kuwahara, H., and Kunitake, T., Self-assembly of bilayers from double-chain fluorocarbon amphiphiles in aprotic solvents: thermodynamic origin and generalization of the bilayer assembly, J. Am. Chem. Soc.,116, 5579, 1994.
30. Riess, J. G., Ed., Blood Substitutes and Related Products: The fluorocarbon Approach, Proc. Int. Symp. Blood Substitutes, Vol. Ill, Art. Cells, Blood Subst., Immob. Biotech.,22, 1994.
31. Riess, J. G., Overview on progress in the fluorocarbon approach to in vivo oxygen delivery, in Blood Substitutes and Oxygen Carriers, Chang, T. M. S., Ed., Marcel Dekker, New York, 1993, 24.
32. Zuck, T. F. and Riess, J. G., Current status of injectable oxygen carriers, Crit. Rev. Clin. Lab. Sci.,31, 295, 1994.
33. Riess, J. G., Pace, S., and Zarlf, L., Highly effective surfactants with low hemolytic activity, Adv. Mater.,3, 249, 1991.
34. Ostro, M. J., Ed., Liposomes: From Biophysics to Therapeutics, Marcel Dekker, New York, 1987.
35. Friberg, S. and Lindman, B., Eds., Organized Solutions. Surfactants in Science and Technology, Marcel Dekker, New York, 1992.
36. Murakami, Y., Supramolecular Assemblies, Mita Press, Tokyo, 1990.
37. Rosen, M. J., Surfactants and Interfacial Phenomena, John Wiley & Sons, New York, 1978.
38. Bondi, A., Van der Waals volumes and radii, J. Phys. Chem.,68, 441, 1964.
39. Tiddy, G. J. T., Concentrated surfactant systems, in Modern Trends of Colloid Science in Chemistry and Biology, Eicke, E., Ed., Birkäuser Verlag, Basel, 1985, 148.
40. xOH, in aqueous solution, J. Phys. Chem.,86, 541, 1982.
41. Tanford, C., The Hydrophobic Effect,2nd ed., John Wiley & Sons, New York, 1980.
42. Israelachvili, J. N., Mitchell, D. J., and Ninham, B. W., Theory of self-assembly of lipid bilayers and vesicles, Biochim. Biophys. Acta,470, 185, 1977.
43. Weast, R. C. and Astle, M. J., Eds., CRC Handbook of Chemistry and Physics,63rd ed., CRC Press, Boca Raton, FL, 1982.
44. Asakawa, T., Mouri, M., Miyagishi, S., and Nishida, M., Probe methods for the second cmc of fluorocarbon and hydrocarbon surfactant mixtures, Langmuir,5, 343, 1989.
45. Hoffmann, H., Kalus, J., and Thurn, H., Small angle neutron scattering measurements on micellar solutions of perfluor detergents, Colloid Polym. Sci.,261, 1043, 1983.
46. l6 segment monitored by fluorescence, J. Am. Chem. Soc.,112, 2821, 1990.
47. Gruen, D. W. R., A model for the chains in amphiphilic aggregates. II. Thermodynamic and experimental comparisons for aggregates of different shape and size, J. Phys. Chem.,89, 153, 1985.
48. Flory, P. J., Statistical Mechanics of Chain Molecules, Interscience Publishers, New York, 1969, 153.
49. Rigby, H. A. and Bunn, C. W., A room temperature transition in polytetrafluoroethylene, Nature,164, 583, 1949.
50. Furukawa, G. T., McCoskey, R. E., and King, G. J., Calorimetric properties of polytetrafluoroethylene (Teflon), J. Res. Nat. Bur. Stand.,49, 273, 1952.
51. Shinoda, K., Hato, M., and Hayashi, T., The physicochemical properties of aqueous solutions of fluorinated surfactants, J. Phys. Chem.,76, 909, 1972.
52. Smart, B. E., in The Chemistry of Functional Groups, Suppl. D. The Chemistry of Halides, Pseudo Halides and Azides, Part 2, Patai, S. and Rappoport, Z., Eds., John Wiley & Sons, Chichester, 1983, 603.
53. Riess, J. G., Perfluorochemical emulsions for intravascular use: principles, materials and methods, in Fluorine in Medicine, Banks, R. E. and Lowe, K. C., Eds., Rapra Technology Ltd, Shawbury, 1994, paper 20.
54. Mukerjee, P. and Handa, T., Adsorption of fluorocarbon and hydrocarbon surfactants to air-water, hexane-water, and perfluorohexane-water interfaces. Relative affinities and fluorocarbon-hydrocarbon ijonideality effects, J. Phys. Chem.,85, 2298, 1981.
55. Mukerjee, P., Fluorocarbon-hydrocarbon interactions in micelles and other lipid assemblies, at interfaces and in solutions, Colloids Surf.,84, 1, 1994.
56. Schneider, J., Erdelen, C., Ringsdorf, H., and Rabolt, J. F., Structural studies of polymers with hydrophilic spacer groups. II. Infrared spectroscopy of Langmuir-Blodgett multilayers of polymers with fluorocarbon side chains at ambient and elevated temperature, Macromolecules,22, 3475, 1989.
57. Mukerjee, P. and Mysels, K. J., Critical micelle concentrations of aqueous surfactant systems, NSRDS-NBS-36, U.S. Government Printing Office, Washington, D.C., 1971.
58. Mathis, G., Leempoel, P., Ravey, J. C., Selve, C., and Delpuech, J. J., A novel class of nonionic microemulsions: fluorocarbons in aqueous solutions of fluorinated poly(oxyethylene) surfactants, J. Am. Chem. Soc.,106,6162,1984.
59. Ravey, J. C., Gherbi, A., and Stébé, M. J., Comparative study of fluorinated and hydrogenated nonionic surfactants. I. Surface activity properties and critical concentrations, Prog. Colloid Polym. Sci.,76, 234, 1988.
60. Kunieda, H. and Shinoda, K., Krafft points, critical micelle concentrations, surface tension, and solubilizing power of aqueous solutions of fluorinated surfactants, J. Phys. Chem.,80, 2468, 1976.
61. Riess, J. G., Greiner, J., Abouhilale, S., and Milius, A., Stabilization of fluorocarbon emulsions by sugar-derived perfluoroalkylated surfactants and co-surfactants, Prog. Colloid Polym. Sci.,88, 123, 1992.
62. Selve, C. and Achilefu, S., Synthesis of monodisperse perfluoroalkyl-oxyethylene surfactants with methoxy capping: surfactants of high chemical inertness, J. Chem. Soc., Chem. Commun,911, 1990.
63. Maurizls, J. C., Pavia, A. A., and Pucci, B., Efficiency of nonionic telomeric surfactants for the solubilization of subcellular fractions proteins, Bioorg. Med. Chem. Lett.,3, 161, 1993.
64. 558, composant membranaire de la NADPH oxydase de neutrophiles humains, Eur. J. Clin. Invest., 25(Suppl. 2), Abstr. 141, 1995.
65. Fung, B. M., Mamrosh, D. L., O’Rear, E. A., Fresh, C. B., and Afzal, J., Unusual micellar properties of a new class of fluorinated nonionic surfactants, J. Phys. Chem.,92, 4405, 1988.
66. Guo, W., Brown, T. A., and Fung, B. M., Micelles and aggregates of fluorinated surfactants, J. Phys. Chem.,95, 1829, 1991.
67. Jones, M. N., Carbohydrate-mediated liposomal targeting and drug delivery, Adv. Drug Delivery Rev., 13, 215, 1994.
68. Laschewsky, A., Ringsdorf, H., and Schmidt, G., Polymerization of hydrocarbon and fluorocarbon amphiphiles in Langmuir-Blodgett multilayers, Thin Solid Films,134, 153, 1985.
69. Higashi, N. and Kunitake, T., Stabilization and facilitated deposition of surface monolayers of fluorocarbon amphiphiles through polyion complex formation, Chem. Lett.,105, 1986.
70. Erdelen, C., Laschewsky, A., Ringsdorf, H., Schneider, J., and Schuster, A., Thermal behaviour of polymeric Langmuir-Blodgett multilayers, Thin Solid Films,180, 153, 1989.
71. Klassen, J. K., Mitchell, M. B., Govoni, S. T., and Nathanson, G. M., Insoluble perfluorinated monolayers and thin films on the surfaces of corrosive acids, J. Phys. Chem.,97, 10166, 1993.
72. Li, M., Acero, A. A., Huang, Z., and Rice, S. A., Formation of an ordered Langmuir monolayer by a non-polar chain molecule, Nature,367, 151, 1994.
73. Santaella, C. and Vierling, P., unpublished results, 1994.
74. Jacquemain, D., Grayer Wolf, S., Leveiller, F., Deutsch, M., Kjaer, K., Als-Nielsen, J., Lahav, M., and Leiserowitz, L., Two-dimensional crystallography of amphiphilic molecules at the air-water interfaces, Angew. Chem., Int. Ed. Engl.,31, 130, 1992.
75. Barton, S. W., Goudot, A., Bouloussa, O., Rondelez, F., Lin, B., Novak, F., Acero, A., and Rice, S. A., Structural transitions in a monolayer of fluorinated amphiphile molecules, J. Chem. Phys.,96, 1343, 1992.
76. Shin, S., Collazo, N., and Rice, S. A., A molecular dynamics study of the packing structures in monolayers of partially fluorinated amphiphiles, J. Chem. Phys.,96, 1352, 1992.
77. Collazo, N., Shin, S., and Rice, S. A., Molecular-dynamics studies of the structure and properties of monolayers of perfluorinated amphiphiles, J. Chem. Phys.,96, 4735, 1992.
78. Lebeau, L., Schultz, P., Célia, H., Mésini, P., Nuss, S., Keinger, C., Ollard, S., Ondet, P., and Nioskowski, C., Specifically designed lipid assemblies as tools for two dimensional crystallization of soluble biological macromolecules, in Handbook of Nonmedical Applications of Liposomes, Vol. II, Barenholz, Y. and Lasic, D. D., Eds., CRC Press, Boca Raton, FL, 1996, in press.
79. Sasaki, D. Y., Kurihara, K., and Kunitake, T., Self-assembled multifunctional receptors for nucleotides at the air-water interface, J. Am. Chem. Soc.,114, 10994, 1992.
80. Tian, Y., Lian, B., Li, Z., Liang, Y., Lu, L., and Huang, W., Specific and non-specific interaction between double perfluoroalkyl-chain steroidal glycoside monolayers and cellulase at the air-water interfaces, J. Chem. Soc., Chem. Commun.,31, 1993.
81. Kunitake, T., Higashi, N., and Kajiyama, T., Oxygen enrichment by fluorocarbon bilayer films, Chem. Lett.,717, 1984.
82. Higashi, N., Kunitake, T., and Kajiyama, T., Surface structure and oxygen permeation in mixed multibilayer nlms of hydrocarbon and fluorocarbon amphiphiles, Macromolecules,19, 1362, 1986.
83. Takahara, A., Higashi, N., Kunitake, T., and Kajiyama, T., State of aggregation and surface chemical composition of composite thin films composed of polyfvinyl alcohol and fluorocarbon amphiphile, Macromolecules, 21, 2443, 1988.
84. Takahara, A., Morotomi, N., Hiraoka, S., Higashi, N., Kunitake, T., and Kajiyama, T., Analysis of the surface structure of a built-up film of fluorocarbon amphiphile and polymer/(fluorocarbon amphiphile) composite thin film by means of X-ray photoelectron spectroscopy, Macromolecules,22, 617, 1989.
85. Okahata, Y., Ebato, H., and Ye, X., Molecular selective adsorption on a multibilayer-coated piezoelectric crystal, J. Chem. Soc., Chem. Commun.,1037, 1988.
86. Ravey, J. C. and Stébé, M. J., Phase and structure behaviour of fluorinated nonionic surfactant systems, Prog. Colloid Polym. Sei.,73, 127, 1987.
87. Ravey, J. C. and Stébé, M. J., Properties of fluorinated non-ionic surfactant-based systems and comparison with non-fluorinated systems, Colloids Surf.,84, 11, 1994.
88. Fonteil, K. and Lindman, B., Fluorocarbon surfactants. Phase equilibrium and phase structures in aqueous systems of a totally fluorinated fatty acid and some of its salt, J. Phys. Chem.,87, 3289, 1983.
89. El Moujahid, C., Propriétés physicochimiques de systèmes aqueux de tensioactifs non ioniques fluorés, Thèse de Doctorat, Université de Nancy, France, 1993.
90. Tiddy, G. J. T., Fluorocarbon surfactant-water mesomorphic phases. I. Study of the ammonium perfluorooctanoate-water system by optical microscopy and low angle X-ray diffraction, J. Chem. Soc., Faraday Trans. I,68, 608, 1972.
91. Krafft, M. P., Giulieri, F., and Riess, J. G., Can single-chain perfluoroalkylated amphiphiles alone form vesicles and other organized supramolecular systems?, Angew. Chem., Int. Ed. Engl.,32, 741, 1993.
92. Giulieri, F., Krafft, M. P., and Riess, J. G., Stable flexible fibers and rigid tubules made from single-chain perfluoroalkylated amphiphiles, Angew. Chem., Int. Ed. Engl.,33, 1514, 1994.
93. Zarif, L., Gulik-Krzywicki, T., Riess, J. G., Pucci, B., Guedj, C., and Pavia, A. A., Alkyl and perfluoralkyl glycolipid-based supramolecular assemblies, Colloids Surf.,84, 107, 1994.
94. Bleasdale, T. A. and Tiddy, G. J. T., Surfactant liquid crystals, in The Structure, Dynamics and Equilibrium Properties of Colloidal Systems, Bloor, D. M. and Wyn-Jones, E„ Eds., Kluwer Academic, Dordrecht, The Netherlands, 1990, 397.
95. Kunitake, T., Okahata, Y., Shimomura, M., Yasunami, S. I., and Takarabe, K., Formation of stable bilayer assemblies in water from single-chain amphiphiles. Relationship between the amphiphile structure and the aggregate morphology, J. Am. Chem. Soc.,103, 5401, 1981.
96. Menger, F. M. and Yamasaki, Y., Hyperextended amphiphiles. Bilayer formation from single-tailed compounds, J.Am. Chem. Soc.,115, 3840, 1993.
97. Handjani-Vila, R. M., Ribier, A., and Vanlerberghe, G., Les niosomes, in Les Liposomes — Applications Thérapeutiques, Puisieux, F., Delattre, J., Eds., Lavoisier, Paris, 1985, 297.
98. Bouwstra, J. A., Hofland, H. E. J., Gooris, G. S., and Junginger, H. E., Characterization of niosomes, in Emulsions —A Fundamental and Practical Approach, Sjöblom, J., Ed., Kluwer Academic, Dordrecht, The Netherlands, 1992,227.
99. 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, 1371, 1989.
100. Fukuda, H., Kawata, K., Okuda, H., and Regen, S. L., Bilayer-forming ion-pair amphiphiles from single-chain surfactants, J. Am. Chem. Soc.,112, 1635, 1990.
101. Benz, R., Prass, W., and Ringsdorf, H., Black lipid membranes from polymerizable lipids, Angew. Chem., Int. Ed. Engl.,21, 368, 1982.
102. Wakita, M., Edwards, K. A., Regen, S. L., Turner, D., and Grüner, S. M., Use of a polymeric counterion to induce bilayer formation from a single-chain surfactant, J. Am. Chem. Soc.,110, 5221, 1988.
103. Kunitake, T., Okahata, Y., and Yasunami, S., Formation and enhanced stability of fluoroalkyl bilayer membranes, J. Am. Chem. Soc.,104, 5547, 1982.
104. Krafft, M. P., Giulieri, F., and Riess, J. G., Supramolecular assemblies from single-chain perfluoroalkylated phosphorylated amphiphiles, Colloids Surf.,84, 113, 1994.
105. Riess, J. G. and Krafft, M. P., Fluorinated phosphocholine-based amphiphiles as components of fluorocarbon emulsions and fluorinated vesicles, Chem. Phys. Lipids,75, 1, 1995.
106. Krafft, M. P., Rolland, J. P., Vierling, P., and Riess, J. G., New perfluoroalkylated phosphocholines. Effects on particle size and stability of fluorocarbon emulsions, New J. Chem.,14, 869, 1990.
107. Krafft, M. P., Vierling, P., and Riess, J. G., Synthesis and preliminary data on biocompatibility and emulsifying properties of perfluoroalkylated phosphoramidates as injectable surfactants, Eur. J. Med. Chem.,26, 545, 1991.
108. Zarif, L., Guedj, C., Pucci, B., Pavia, A. A., and Riess, J. G., Modular glycolipids with perfluoroalkylated, hydrogenated, or mixed perfluoroalkylated/hydrogenated hydrophobic tails as components for fluorinated vesicles and other supramolecular assemblies, Abstract Int. Symp. Liposomes in Drug Delivery: The Nineties and Beyond, London, 1993, 126.
109. Zarif, L., Gulik-Krzywicki, T., Riess, J. G., Pucci, B., Guedj, C., and Pavia, A. A., unpublished results, 1994.
110. Giulieri, F, and Krafft, M. P., Can the formation of vesicles from single-chain perfluoroalkylated amphiphiles be predicted?, Colloids Surf.,84, 121, 1994.
111. Giulieri, F., Krafft, M. P., and Riess, J. G., Fluorinated vesicles from single-chain perfluoroalkylated amphiphiles, Abstract Int. Symp. Liposomes in Drug Delivery: The Nineties and Beyond, London, 1993, 78.
112. Trevino, L., Krafft, M. P., Frézard, F., Giulieri, F., and Riess, J. G., Fluorinated liposomes. Use of (F-alkyl)alkyl components to impart impermeability to the liposomal membrane, Proc. Int. Symp. Control. Rel. Bioact. Mater.,21, 606, 1994.
113. Santaella, C., Vierling, P., Riess, J. G., Gulik-Krzywicki, T., Gulik, A., and Monasse, B., Polymorphic phase behavior of perfluoroalkylated phosphatidylcholines, Biochim. Biophys. Acta,1190, 25, 1994.
114. Zarif, L., Riess, J. G., Pucci, B., Guedj, C., and Pavia A. A., Double-tailed perfluoroalkylated glycolipids as components for drug delivery and targeting systems. Preliminary biocompatibility results, Art. Cells, Blood Subst., Immob. Biotech.,22, 1485, 1994.
115. Guedj, C., Pucci, B., Zarif, L., Coulomb, C., Riess, J. G., and Pavia, A. A, Vesicles and other supramolecular systems from biocompatible synthetic glycolipids with hydrocarbon and/or fluorocarbon chains, Chem. Phys. Lipids, 72, 153, 1994.
116. Myrtil, E., Zarif, L., Greiner, J., Riess, J. G. Pucci, B., and Pavia, A. A., Double-tailed perfluoroalkyl telomeric surfactants derived from tris(hydroxymethyl)-acrylamidomethane for medical applications, Macromol. Chem. Phys., 195, 1289, 1994.
117. Myrtil, E., Zarif, L., Greiner, J., Riess, J. G. Pucci, B., and Pavia, A. A., unpublished results, 1994.
118. Sternberg, B., Zarif, L., Greiner, J., and Riess, J. G., unpublished results, 1994.
119. Trevino, L., Frézard, F., Rolland, J. P., Postel, M., and Riess, J. G., Novel liposome systems based on the incorporation of (perfluoroalkyl)alkenes (FmHnE) into the bilayer of phospholipid liposomes, Colloids Surf.,84, 223, 1994.
120. Trevino, L., Frézard, F., Postel, M., and Riess, J. G., Incorporation of a (perfluoroalkyl)alkane into the phospholipid bilayer of DMPC liposomes results in greater encapsulation stability, J. Liposome Res.,4, 1017, 1994.
121. Riess, J. G., Sole-Violan, L., and Postel, M., A new concept in the stabilization of injectable fluorocarbon emulsions: the use of mixed fluorocarbon-hydrocarbon dowels, J. Dispersion Sci. Technol.,13, 349, 1992.
122. Riess, J. G. and Postel, M., Stability and stabilization of fluorocarbon emulsions destined for injection, Biomat., Art. Cells, Immob. Biotech.,20, 819, 1992.
123. Cornélus, C., Krafft, M. P., and Riess, J. G., Improved control over particles sizes and stability of concentrated fluorocarbon emulsions by using mixed fluorocarbon/hydrocarbon molecular dowels, Art. Cells, Blood Subst., Immob. Biotech.,22, 1183, 1994.
124. Cornélus, C., Krafft, M. P., and Riess, J. G., About the mechanism of stabilization of fluorocarbon emulsions by mixed fluorocarbon/hydrocarbon additives, J. Colloid Interface Sci.,163, 391, 1994.
125. Cornélus, C., Krafft, M. P., and Riess, J. G., The dowel effect — mechanism of stabilization of fluorocarbon emulsions by mixed fluorocarbon/hydrocarbon amphiphiles, Abstract, 14th Int. Symp. Fluorine Chemistry, Yokohama, Japan, 1994, 49.
126. Trevino, L., Postel, M., and Riess, J. G., The dowel effect of (perfluoroalkyl)alkenes at the fluorocarbon/water interface: increased adsorption of sodium laurate, J. Colloid Interface Sci.,166, 414, 1994.
127. Cohen, J. A. and Krafft, M. P., unpublished results, 1994.
128. 2 is slowed down when (perfluoroalkyl)alkanes are incorporated into the liposomal membrane, Biochim. Biophys. Acta,1254, 1, 1994.
129. Zarif, L., Postel, M., Septe, B., Trevino, L., Riess, J. G., Mahé, A. M., and Follana, R., Biodistribution and excretion of mixed fluorocarbon-hydrocarbon dowel molecules used as stabilizers of fluorocarbon emulsions. A quantitative study by fluorine NMR, Pharm. Res.,11, 122, 1994.
130. Schnur, J. M., Lipid tubules: a paradigm for molecularly engineered structures, Science,262, 1669, 1993.
131. Krafft, M. P., Giulieri, F., and Riess, J. G., Enhanced proclivity to self-aggregation of phosphorous-based amphiphiles when fluorinated: the (perfluoroakyl)alkyl dimorpholinophosphates, in Phosphorous, Sulfur, Silicon, in press.
132. Giulieri, F., Krafft, M. P., and Riess, J. G., About the self-organization of single chain fluorinated amphiphiles with fluorinated alcohols, Thin Solid Films, in press.
133. El Ghoul, M., Rico, I., and Lattes, A., Colloids Surf., in press.
134. Guillod, F., Synthèse et évaluation physico-chimique de glycophospholipides perfluoroalkylés composants de liposomes pour la vectorisation de principes actifs, Thèse de Doctorat, Université de Nice, France, 1994.
135. Guillod, F., Giulieri, F., Greiner, J., Krafft, M. P., and Riess, J. G., unpublished results, 1994.
136. Papahadjopoulos, D., Wail, W. J., Jacobson, K., and Poste, G., Cochleate lipid cylinders: formation by fusion of unilamellar vesicles, Biochim. Biophys. Acta,394, 483, 1975.
137. Fuhrhop, J. H., Schnieder, P., Rosenberg, J., and Boekema, E., The chiral bilayer effect stabilizes micellar fibers, J. Am. Chem. Soc.,109, 3387, 1987.
138. Fuhrhop, J. H., Demoulin, C., Rosenberg, J., and Boettcher, C., Cloth-like aggregates of micellar fibers made of N-dodecyltartaric acid monoamides, J. Am. Chem. Soc.,112, 2827, 1988.
139. Imae, T., Takahashi, Y., and Muramatsu, H., Formation of fibrous molecular assemblies by amino acids surfactants in water, J. Am. Chem. Soc.,114, 3414, 1992.
140. Newkome, G. R., Baker, G. R., Arai, S., Saunders, M. J., Russo, P. S., Theriot, K. J., Moorefield, C. N., Rogers, L. E., Miller, J. E., Lieux, T. R., Murray, M. E., Phillips, B., and Pascal, L., Synthesis and characterization of two-directional Cascade molecules and formation of aqueous gels, J. Am. Chem. Soc.,112, 8458, 1990.
141. Russel, T. P., Rabolt, J. F., Twigg, R. T., Siemens, R. L., and Farmer, B. L., Structural characterization of semi-fluorinated n-alkanes. II. Solid-solid transition behavior, Macromolecules,19, 1135, 1986.
142. Turberg, M. P. and Brady, J. E., Semifluorinated hydrocarbons: primitive surfactant molecules, J. Am. Chem. Soc.,110, 7797, 1988.
143. Ishikawa, Y., Kuwahara, H., and Kunitake, T., Self-organization of solvophobic double-chained fluorocarbon derivatives in organic media, Chem. Lett.,1737, 1989.
144. Ishikawa, Y., Kuwahara, H., and Kunitake, T., Self-assembly of bilayer membranes in organic solvents by novel “amphiphilic” compounds, J. Am. Chem. Soc., ill, 8530, 1989.
145. Kuwahara, H., Hamada, M., Ishikawa, Y., and Kunitake, T., Self-organization of bilayer assemblies in a fluorocarbon medium, J. Am. Chem. Soc.,115, 3002, 1993.
146. Riess, J. G., Greiner, J., Abouhilale, S., and Milius, A., Stabilization of fluorocarbon emulsions by sugar-derived perfluoroalkylated surfactants and co-surfactants, Progr. Colloid Polym. Sci.,88, 123, 1992.
147. Stadtler, V., Krafft, M. P., and Riess, J. G., Water-in-fluorocarbon emulsions for drug delivery, Proc. Int. Symp. Control. Rel. Bioactive Mater.,22, 464, 1995.
148. Rosano, H. L. and Gerbacia, W. E., Fluorocarbon microemulsions, U.S. Patent 2,452,513, 1975.
149. Robert, A. and Tondre, C., Solubilization of water in binary mixtures of fluorocarbon and nonionic fluorinated surfactants: existence domains of reverse microemulsions, J. Colloid Interface Sci.,98, 515, 1984.
150. Lattes, A. and Rico-Lattes, I., Microemulsions of perfluorinated and semi-fluorinated compounds, Art. Cells, Blood Subst., Immob. Biotech., 22,1007, 1994.
151. Schubert, K. V. and Kaler, E. W., Microemulsifying fluorinated oils with mixtures of fluorinated and hydrogenated surfactants, Colloids Surf.,84, 97, 1994.
152. Krafft, M. P. and Riess, J. G., Stable highly concentrated fluorocarbon gels, Angew. Chem., Int. Ed. Engl.,33, 1100, 1994.
153. Krafft, M. P. and Riess, J. G., Fluorocarbon polyaphrons, Abstracts 14th Int. Symp. on Fluorine Chemistry, Yokohama, Japan, 1994, 255.
154. Solans, C., Dominguez, J. G., Parra, J. L., Heuser, J., and Friberg, S. S., Gelled emulsions with a high water content. Colloid Polym. Sci.,266, 570, 1988.
155. Kunieda, H., Solans, C., Shida, N., and Parra, J. L., The formation of gel-emulsions in a water/nonionic surfactant/oil system, Colloids Surf.,24, 225, 1987.
156. Ravey, J. C. and Stébé, M. J., Structure of inverse micelles and emulsions-gels with fluorinated nonionic surfactants. A small-angle neutron scattering study, Prog. Colloid. Polym. Sci.,82, 218, 1990.
157. Ravey, J. C. and Stébé, M. J., Small angle neutron scattering studies of aqueous gels with fluorinated nonionic surfactants, Physica B,156-157, 394, 1989.
158. Pons, R., Erra, P., Solans, C., Ravey, J. C., and Stébé, M. J., Viscoelastic properties of gel-emulsions: their relationship with structure and equilibrium properties, J. Phys. Chem.,97, 12320, 1993.
159. Riess, J. G., Santaella, C., and Vierling, P., New perfluoroalkylated phosphatidylcholines as surfactants for biomedical applications, Proc. XXII CED Meeting on Surfactants, Palma de Mallorca, Comité Espagnol Detergencia, Tensioactivos y Afines, Ed., Barcelona, 1991, 157.
160. Santaella, C., Vierling, P., and Riess, J. G., Highly stable liposomes derived from perfluoroalkylated glycerophophocholines, Angew. Chem., Int. Ed. Engl.,30, 567, 1991.
161. Kunitake, T., Ando, R., and Ishikawa, Y., DSC studies of the phase transition behavior of synthetic bilayer membranes. II. Bilayer membranes of single-chain and triple-chain amphiphiles, Mem. Fac. Eng., Kyushu Univ.,46, 245, 1986.
162. Ravily, V., Gaenztler, S., Santaella, C., and Vierling, P., unpublished results, 1994.
163. Phospholipids Handbook, Cevc, G., Ed., Marcel Dekker, New York, 1993.
164. Clary, L., Santaella, C., and Vierling, P., unpublished results, 1994.
165. Kunitake, T., Ando, R., and Ishikawa, Y., DSC studies of the phase transition behavior of synthetic bilayer membranes. I. Bilayer membranes of double-chain amphiphiles, Mem. Fac. Eng., Kyushu Univ.,46, 221, 1986.
166. 19F-NMR, Sci. Eng. Rev., Doshisha Univ.,29, 24, 1988.
167. Kunitake, T. and Higashi, N., Bilayer membranes of triple-chain, fluorocarbon amphiphiles, J. Am. Chem. Soc.,107, 692, 1985.
168. Rolland, P., Santaella, C., and Vierling, P., unpublished results, 1994.
169. Mabray, S. and Sturtevant, J. M., Investigation of phase transitions of lipids and lipid mixtures by high sensitivity differential scanning calorimetry, Proc. Natl. Acad. Sci. U.S.A.,73, 3862, 1976.
170. Shinkai, S., Torigoe, K., Manabe, O., and Kajiyama, T., Complete thermocontrol of ion permeation through ternary composite membranes composed of polymer-liquid crystal-fluorocarbon-containing crown ethers, J. Chem. Soc., Chem. Commun.,933, 1986.
171. Shinkai, S., Torigoe, K., Manabe, O., and Kajiyama, T., Temperature regulation of crown-mediated ion transport through polymer/liquid crystal composite membranes. Remarkable transport ability of fluorocarbon-containing crown ethers, J. Am. Chem. Soc.,109, 4458, 1987.
172. Ihara, H., Hashiguchi, Y., and Kunitake, T., Functional fluorocarbon micelles. Phase separation and reactivity change of hydroxamate nucleophiles in mixed micelles of hydrocarbon and fluorocarbon surfactants, Chem. Lett.,733, 1983.
173. Kunitake, T., Ihara, H., and Hashiguchi, Y., Functional fluorocarbon micelles. Specific rate enhancement in the catalytic hydrolysis of phenyl esters due to selective binding of fluorocarbon and hydrocarbon substrates, J. Am. Chem. Soc.,106, 1156, 1984.
174. Liang, K. and Hui, Y., Vesicle of a hybrid bolaamphiphile: flip-flop behavior of spin labels, J. Am. Chem. Soc., 114, 6588, 1992.
175. Liang, K. and Hui, Y., Biphasic kinetics and flip-flop behaviour of vesicles of fluorocarbon amphiphiles with a 1,3-disubstituted glycerol structure, J. Phys. Org. Chem.,5, 715, 1992.
176. Senior, J. and Gregoriadis, G., Stability of small unilamellar liposomes in serum and clearance from the circulation: the effect of the phospholipid and cholesterol components, Life Sci.,30, 2123, 1982.
177. Kirby, C., Clarke, J., and Gregoriadis, G., Effect of the cholesterol content of small unilamellar liposomes on their stability in vivo andin vitro, Biochem. J.,186, 591, 1980.
178. Frézard, F., Santaella, C., Vierling, P., and Riess, J. G., Permeability and stability in buffer and in human serum of fluorinated phospholipid-based liposomes, Biochim. Biophys. Acta,1192, 61, 1994.
179. Frézard, F., Santaella, C., Vierling, P., and Riess, J. G., unpublished results, 1992.
180. Guillod, F., Greiner, J., Milius, A., and Riess, J. G., Amphiphilic sugar phosphates with single or double perfluoroalkylated hydrophobic chains for use in oxygen and drug delivery systems, Art. Cells, Blood Subst., Immob. Biotech.,22, 1273, 1994.
181. Guillod, F., Greiner, J., and Riess, J. G., unpublished results, 1994.
182. Papahadjopoulos, D., Nir, S., and Ohki, S., Permeability properties of phospholipid membranes: effect of choles terol and temperature, Biochim. Biophys. Acta,266, 561, 1971.
183. Bresselers, J. M., Goderis, H. L., and and Tobback, P. P., Measurement of the glucose permeation rate across phospholipid bilayers using small unilamellar vesicles, Biochim. Biophys. Acta,772, 374, 1984.
184. + permeability, active doxorubicin encapsulation and stability in human serum, Biochim. Biophys. Acta,1194, 61,1994.
185. Kunitake, T., Okahata, Y., and Yasunami, S., Substrate entrapment and formation of pH gradient in ammonium bilayer vesicles, Chem. Lett.,1397, 1981.
186. Mahe, A. M., Manoux, J., Valla, A., Follana, R., Zarif, L., Greiner, J., Vierling, P., and Riess, J. G., Perfluoroalkylated surfactants: relationships between structure and acute toxicity in mice, Biomat., Art. Cells, Immob. Biotech.,20, 839, 1992.
187. Santaella, C., Frezard, F., Vierling, P., and Riess, J. G., Extended in vivo blood circulation time of fluorinated liposomes, FEBS Lett.,336, 481, 1993.
188. Allen, T. M. and Chonn, A., Large unilamellar liposomes with low uptake into the reticuloendothelial system, FEBS Lett.,223, 42, 1987.
189. Gabizon, A. and Papahadjopoulos, D., Liposome formulations with prolonged circulation time in blood and enhanced uptake by tumors, Proc. Natl. Acad. Sci. U.S.A.,85, 6949, 1988.
190. Lasic, D. D., Sterically stabilized vesicles, Angew. Chem., Int. Ed. Engl.,33, 1685, 1994.
191. Gregoriadis, G., Liposomes as Drug Carriers: Recent Trends and Progress, John Wiley & Sons, Chichester, 1988.
192. Scherphof, G., Damen, J., and Hoekstra, D., Interactions of liposomes with plasma proteins and components of the immune systems, in Liposomes: From Structure to Therapeutic Applications, Knight, C. G., Ed., Elsevier, Amsterdam, 1981, 299.
193. Szonyi, S. and Cambon, A., New synthetic strategy to vesicle-forming perfluoroalkylated amphiphiles, New. J. Chem.,17, 425, 1993.
194. Trabelsi, H., Szonyi, S., Gaysinski, M., and Cambon, A., Synthesis and vesicle formation of cationic surfactants based on trisubstituted perfluoroalkylated thiourea, Langmuir,9, 1201, 1993.
195. Liang, K. and Hui, Y., Characterization and phase transition study for vesicles of fluorocarbon amphiphiles with 1,3-disubstituted glycerol structure, Chin. J. Chem., 10, 396, 1992.
196. Guillod, F., Greiner, J., and Riess, J. G., Synthesis of double-tailed (perfluoroalkyl)alkyl phosphosugars: new components for drug-carrying and -targeting systems, Carbohydr. Res.,261, 37, 1994.
197. Higashi N., Adachi T., and Niwa M., Molecular weight control of photopolymerization at an oriented bilayer surface using phase separation of fluorocarbon- and hydrocarbon-amphiphiles, J. Chem. Soc., Chem. Commun.,1573, 1988.
198. Gu, J. H., Luo, S. M., Kong, H. K., and Hui, Y. Z., Synthesis of fluorocarbon phospholipids and the formation of their liposomes, Acta Chim. Sin.,46, 913, 1988.
199. Montisci, M. J. M., Clary, L., Ravily, V., Santaella, C., and Vierling, P., unpublished results, 1994.