Sugar-based surfactants with isoprenoid-type hydrophobic chains: Physicochemical and biophysical aspects

Sugar-Based Surfactants: Fundamentals and Applications

Volumn , Issue , 2008, Pages 361-411

  Hato, Masakatsu ^a   Minamikawa, Hiroyuki ^b   Kato, Tadashi ^c  

^a RIKEN YOKOHAMA INSTITUTE   (Japan)

^b NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

^c TOKYO METROPOLITAN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GENE TRANSFER; HYDROPHOBICITY;

GENE DELIVERY; HYDROPHOBIC CHAINS; ISOPRENOIDS; RECENT RESEARCHES; RENEWABLE RESOURCE; SUGAR-BASED SURFACTANTS;

SURFACE ACTIVE AGENTS;

EID: 84891416160     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1201/9781420051674     Document Type: Chapter

References (136)

1. Hill, K., von Rybinski, W., and Stoll, G., Alkyl Polyglycosides. VCH, Weinheim, 1997.
2. Kitamoto, D., Toma, K., and Hato, M., in Handbook of Nanostructured Biomaterials and Their Applications in Nano-biotechnology, Vol.1., Nalwa, S. H., Ed., American Scientific Publishers, Stevenson Ranch, 2005, Chapter 6.
3. Laughlin, R. G., in The Aqueous Phase Behavior of Surfactants. Academic Press, London, 1994, Chapters 3 and 5.
4. Shinoda, K., in Solution and Solubility, 3rd ed., Maruzen, Tokyo, 1991, Chapter 1.
5. Jeffrey, G. A., Acc. Chem. Res., 1986, 19, 168.
6. Abe, Y., Harata, K., Fujiwara, M., and Ohbu, K., J. Chem. Soc. Perkin Trans., 1998, 2, 177.
7. Hato, M., Curr. Opin. Colloid Interface Sci., 2001, 6, 268.
8. Boyd, B. J., Drummond, G. J., Krodkiewska, I., and Grieser, F., Langmuir, 2000, 16, 7359.
9. Sakya, P., Seddon, J. M., and Vill, V., Liq. Cryst., 1997, 23, 409.
10. Shinoyama, H., Gama, Y., Nakahara, H., Ishigami, Y., and Yasui, T., Bull. Chem. Soc. Jpn., 1991, 64, 29.
11. Nilsson, F., Soderman, O., Hansson, P., and Johansson, I., Langmuir, 1998, 14, 4050.
12. Koynova, R. and Caffrey, M., Chem. Phys. Lipids, 1994, 69, 181.
13. Kates, M., in Handbook of Lipid Research 6, Glycolipids, Phosphoglycolipids, and Sulfoglycolipids, Kates, M., Ed., Plenum Press, New York and London, 1990, pp. 1-122.
14. Smith, P. F., in Microbial Lipids, Vol. 1, Ratledge, C. and Wilkinson, S. G., Eds., Academic Press, New York, 1988, pp. 489-525.
15. Langworthy, T. A. and Pond, J. L., in Thermophiles: General, Molecular, and Applied Microbiology, Brock, T. D., Ed., John Wiley & Sons, New York, 1986, pp. 107-135.
16. Fischer, E. and Helperich, B., Justus Liebigs Ann. Chem., 1911, 383, 68.
17. Fischer, E., Ber. Dtsh. Chem. Ges., 1893, 26, 2400.
18. Konigs, W. and Knorr, E., Ber., 1901, 34, 957.
19. Veeneman, G. H., in Carbohydrate Chemistry, Boon G.-J., Ed., Blackie Academic & Professional, London, 1998, Chapter 4.
20. Schmidt, R. R. and Klager, R., Angew. Chem., Int. Ed. Engl., 1985, 24, 65.
21. Schmidt, R. R., Angew. Chem., Int. Ed., Engl., 1986, 25, 212.
22. Minamikawa, H., Murakami, T., and Hato, M., Chem. Phys. Lipids, 1994, 72, 111.
23. Exoffier, G., Gagnaire, D. G., and Utille, J.-P., Carbohydr. Res., 1975, 39, 368.
24. Urban, F. J., Moore, B. S., and Breitenbach, R., Tetrahedron Lett., 1990, 31, 4421.
25. Hanessian, S. and Banoub, J., Carbohydr. Res., 1997, 59, 261.
26. Salkar, R. J., Minamikawa, H., and Hato, M., Chem. Phys. Lipids, 2004, 127, 65.
27. Minamikawa, H. and Hato, M., Langmuir, 1997, 13, 2564.
28. Minamikawa, H. and Hato, M., Langmuir, 1998, 14, 4503.
29. Hato, M., Yamashita, I., Kato, K., and Abe, Y., Langmuir, 2004, 20, 11366.
30. Milkereit, G., Garamus, V. M., Yamashita, J., Hato, M., Morr, M., and Vill, V., J. Phys. Chem. B., 2005, 109, 1599.
31. Hato, M., Seguer, J. B., and Minamikawa, H., Stud. Surf. Sci. Catal., 2001, 132, 725.
32. Hato, M. and Minamikawa, H., Langmuir, 1996, 12, 1658.
33. Nilsson, F., Soderman, O., and Reimer, J., Langmuir, 1998, 14, 6396.
34. Lang, J. C. and Morgan, R. D., J. Chem. Phys., 1980, 73, 5849.
35. Kahlweit, M. and Strey, R., Angew. Chem. Int. Ed. Engl, 1985, 24, 654.
36. Minamikawa, H. and Hato, M., Chem. Phys. Lipids, 2005, 134, 151.
37. Hato, M., Minamikawa, H., Salkar, R. A., and Matsutani, S., Progr. Colloid Polym. Sci., 2004, 127, 65.
38. Hato, M., Minamikawa, H., Salkar, R. A., and Matsutani, S., Langmuir, 2002, 18, 3425.
39. Hyde, S. T., Andersson, S., Ericsson, B., and Larsson, K., Z. Kristallogr., 1984, 168, 213.
40. Turner, D. C., Wang, Z.-G., Gruner, S. M., Mannock, D. A., and McElhaney, N., J. Phys. II France, 1992, 2, 2039.
41. Barauskas, J. and Landh, T., Langmuir, 2003, 19, 9562.
42. Seddon, J. M., Biochemistry, 1990, 29, 7997.
43. Seddon, J. M., Bartle, E. A., and Mingins, J., J. Phys. Condens. Matter, 1990, 2, SA285.
44. Kennedy, J. F., in Carbohydrate Chemistry, Kennedy, J. F., Ed., Clarendon Press, Oxford, 1988, Chapter 1.
45. Tamada, K., Minamikawa, H., Hato, M., and Miyano, K., Langmuir, 1996, 12, 1666.
46. Baba, T., Toshima, Y., Minamikawa, H., Hato, M., Suzuki, K., and Kamo, N., Biochim. Biophys. Acta, 1999, 1421, 91.
47. Nilsson, F., Soderman, O., and Johansson, I., Langmuir, 1996, 12, 902.
48. Wieslander, A., Ulmius, J., Lindblom, G., and Fontell, K., Biochim. Biophys. Acta, 1978, 512, 241.
49. McDaniel, R. V., Biochim. Biophys. Acta, 1998, 940, 158.
50. Larsson, K., in Lipids-Molecular Organization, Physical Functions and Technical Applications, The Oily Press, Dundee, 1994, Chapter 3.
51. Chapman, R. M., Williams, B. D., and Ladbrooke, B. D., Chem. Phys. Lipids., 1967, 1, 445.
52. Gruner, S. M., Tate, M. W., Kirk, G. L., So, P. T. C., Turner, D. C., Keane, D.T., Tilcock, C. P. S., and Cullis, P. R., Biochemistry, 1988, 27, 2853.
53. Shipley, G. G., Green, J. P., and Nichols, B. W., Biochim. Biophys. Acta, 1973, 311, 53.
54. We, Y., He, K., Ludtke, S. J., and Huang, H. W., Biophys. J., 1995, 68, 2361.
55. Nagel, J. F., Zhang, R., Tristram-Nagle, S., Sun, W., Petrache, H. L., and Suter, R. M., Biophys. J., 1995, 68, 2361.
56. Gounaris, K., Mannock, D. A., Sen, A., Brain, A. P. R., Williams, W. P., and Quinn, J. P., Biochim. Biophys. Acta, 1983, 732, 229.
57. Mannock, D. A., Lewis, R. N. A. H., Sen, A., and McElhaney, R. N., Biochemistry, 1988, 27, 6852.
58. Hinz, H. J., Kuttenreich, H., Meyer, R., Renner, M., and Frund, R., Biochemistry, 1991, 30, 5125.
59. Endo, T., Inoue, K., and Nojima, S., J. Biochem. (Tokyo), 1982, 92, 953.
60. Iwamoto, K., Sunamoto, J., Inoue, K., Endo, T., and Nojima, S., Biochim. Biophys. Acta, 1982, 691, 44.
61. Shinoda, W., Mikami, M., Baba, T., and Hato, M., J. Phys. Chem. B, 2003, 107, 14030.
62. Shinoda, W., Mikami, M., Baba, T., and Hato, M., J. Phys. Chem. B, 2004, 108, 9346.
63. Shinoda, W., Mikami, M., Baba, T., and Hato, M., Chem. Phys. Lett., 2004, 390, 35.
64. Degani, H., Danon, A., and Caplan, S. R., Biochemistry, 1980, 19, 1626.
65. Baba, T., Minamikawa, H., Hato, M., and Handa, T., Biophys. J., 2001, 81, 3377.
66. Holmes, M. C., and Charvolin, J., J. Phys. Chem., 1984, 88, 810.
67. Kekicheff, P., Cabane, B., and Rawiso, M., J. Physique, Lett., 1984, 45, L-813.
68. Funari, S. S., Holmes, M. C., and Tiddy, G. J. T., J. Phys. Chem., 1994, 98, 3015.
69. Fairhurst, C. E., Holmes, M. C., and Leaver, M. S., Langmuir, 1997, 17, 4964.
70. Gustafsson, J., Oradd, G., Lindblom, G., Olsson, U., and Almgren, M., Langmuir, 1997, 13, 852.
71. Minewaki, K., Kato, T., Yoshida, H., Imai, M., and Ito, K., Langmuir, 2001, 17, 1864.
72. Hyde, S. T., Colloque de Physique, 1990, 51, C7.
73. Hyde, S. T., Colloids Surf. A, 1995, 103, 227.
74. Yamashita, I., Kawabata, Y., Kato, T., Hato, M., and Minamikawa, H., Colloids Surf. A, 2004, 250, 485.
75. Dorfler, H.-D. and Gopfert, A., J. Disp. Sci. Technol., 1999, 20, 35-58.
76. Hato, M., Minamikawa, H., and Seguer, J. B., J. Phys. Chem. B., 1998, 102, 11035.
77. Shinoda, K., Yamaguchi, T., and Hori, R., Bull. Chem. Soc. Jpn., 1961, 34, 237.
78. Aveyard, R., Binks, B. P., Chen, J., and Fletcher, I., Langmuir, 1998, 14, 4699.
79. De Grip, W. J. and Bovee-Geurts, P. H. M., Chem. Phys. Lipids, 1979, 23, 321.
80. Israelachvili, J., in Intermolecular and Surface Forces, 2nd ed., Academic Press, New York, 1992, Chapter 17.
81. Kato, T., Kawabata, Y., Fujii, M., Kato, T., Hato, M., and Minamikawa, H., J. Colloid Interface Sci., 2007, 312, 122.
82. Focher, B., Savelli, G., Torri, G., Vecchio, G., McKenzie, D. C., Nicoli, D. F., and Bunton, C. A., Chem. Phys. Lett., 1989, 158, 491.
83. He, L., Garamus, V. M., Funari, S. S., Malfois, M., Willumeit, R., and Niemeyer, B., J. Phys. Chem. B., 2002, 106, 7596
84. Durpuy, C., Auvray, X., Petipas, C., Rico-Lattes, I., and Lattes, A., Langmuir, 1997, 13, 3965.
85. Ben-Shaul, A. and Gelbart, W. M., in Micelles, Membranes, Microemulsions, and Monolayers, Gelbart, W. M., Ben-Shaul, A., and Roux, D., Eds., Springer, New York, 1994, p. 1.
86. Nilsson, F., Soderman, O., and Johansson, I., J. Colloid Interface Sci., 1998, 203, 131.
87. Whiddon, C., Soderman, O., and Hansson, P., Langmuir, 2002, 18, 4610.
88. Whiddon, C., Reimer, J., and Soderman, O., Langmuir, 2004, 20, 2172.
89. Miller, C., Ion Channel Reconstitution, Plenum, New York, 1986.
90. Baba, T., Minamiakwa, H., Hato, M., Motoki, A., Hirano, M., Zhou, D., and Kawasaki, K., Biochim. Biophys. Res. Commun., 1999, 265, 734.
91. Baba, T., Zheng, L.-Q., Minamikawa, H., and Hato, M., J. Colloid Interface Sci., 2000, 223, 235.
92. Minami, H., Inoue, T., and Shimozawa, R., Langmuir, 1996, 12, 3574.
93. Gamon, B. L., Virden, J. W., and Berg, J. C., J. Colloid Interface Sci., 1989, 132, 125.
94. Balzer, D., Langmuir, 1993, 9, 3375.
95. Webb, M. S., Tilcock, C. P. S., and Green, B. R., Biochim. Biophys. Acta, 1988, 938, 323.
96. Webb, M. S. and Green, B. R., Biochim. Biophys. Acta, 1990, 1030, 231.
97. Fragata, M., Menikh, A., and Robert, S., J. Phys. Chem., 1993, 97, 13920.
98. Johnsson, M., Wagenaar, A., and Engberts, J. B. F. N., J. Am. Chem. Soc., 2003, 125, 757.
99. Zhang, L., Somasundaran, P., and Maltesh, C., Langmuir, 1996, 12, 2371.
100. Tomoasia-Cotisel, M., Zsako, J., Chifu, E., and Quinn, P. J., Chem. Phys. Lipids, 1983, 34, 55.
101. Johnston, D. S., Coppard, E., and Chapman, D., Biochim. Biophys. Acta, 1985, 815, 325.
102. Verwey, E. J. and Overbeek, J. Th. G., Theory of Stability of Lyophobic Colloid, Elsevier, Amsterdam, 1948.
103. Hogg, R., Healy, T. W., and Fuerstenau, D. W., Trans. Faraday Soc., 1966, 62, 1638.
104. Wiese, G. and Healy, T. W., Trans. Faraday Soc., 1970, 66, 490.
105. Vold, M. J., J. Colloid Sci., 1961, 16, 1.
106. Korchowiec, B. M., Baba, T., Minamikawa, H., and Hato, H., Langmuir, 2001, 17, 1853.
107. Rand, R. P. and Parsegian, V. A., Biochim. Biophys. Acta, 1989, 988, 351.
108. Israelachvili, J. N. and Wennerstrom, H., Nature, 1996, 379, 219.
109. McIntosh, T. J. and Simon, S. A., Biochemistry, 1993, 32, 8374.
110. Helfrich, W., Z. Naturforsch., 1978, 33a, 305.
111. Evans, E. A. and Parsegian, V. A., Proc. Natl. Acad. Sci. U. S. A., 1986, 83, 7132.
112. Blodgett, K. B. and Langmuir, I., Phys. Rev., 1937, 51, 964.
113. Ninham, B. W. and Parsegian, A. D., J. Theor. Biol., 1971, 31, 405.
114. Ohshima, H., Colloid Polym. Sci., 1976, 254, 484.
115. Ohshima, H. and Mitsusi, T., J. Colloid Interface Sci., 1978, 63, 525.
116. Chan, D. Y., Pashley, R. M., and White, L. R., J. Colloid Interface Sci., 1980, 77, 283.
117. Derjaguin, B. V., Kolloid-Z., 1934, 69, 155.
118. Lorenzen, S., Servuss, R. M., and Helfrich, W., Biophys. J., 1986, 50, 565.
119. Evans, E. and Rawicz, W., Phys. Rev. Lett., 1990, 64, 2094.
120. Doppert, H. L. and Staverman, A. J., J. Polym. Sci. A-1, 1966, 4, 2367.
121. Montal, M. and Muller, P., Proc. Natl. Acad. Sci., U. S. A., 1972, 69, 3561.
122. Stern, J., Freisleben, H.-J., Janku, S., and Ring, K., Biochim. Biophys. Acta, 1992, 1128, 227.
123. Gambacorta, A., Gliozzi, A., and Rosa, M. De., J. Microbial. Biotechnol., 1995, 11, 115.
124. Rosa, M. De, Thin Solid Films, 1996, 284/285, 13.
125. Elferink, M. G. L., De Wit, J. G., Driessen, A. J. M., and Konings, W. N., Biochim. Biophys. Acta, 1994, 1193, 247.
126. Dannenmuller, O., Arakawa, K., Eguchi, T., Kakinuma, K., Blanc, S., Albrecht, A.-M., Schumtz, M., Nakatani, Y., and Ourisson, G., Chem. Eur. J., 2000, 6, 645.
127. Hirata, H., Ohno, K., and Tsuda, M., Seibutsubutsuri (Biophysics), 1986, 26, S108.
128. Ikeuchi, M., Bot. Mag. Tokyo, 1992, 105, 327.
129. Nash, D., Miyao, M., and Murata, N., Biochim. Biophys. Acta, 1985, 807, 127.
130. Hato, M., Minamikawa, H., Tamada, K., Baba, T., and Tanabe, Y., Adv. Colloid Interface Sci., 1999, 80, 233.
131. Yamashita, J., Shiono, M., and Hato, M., J. Phys. Chem. B, 2008, in press.
132. Waltermo, A., Manev, E., Pugh, R., and Claesson, P. M., J. Disp. Sci. Technol., 1994, 15, 273.
133. Person, C. M. and Claesson, P. M., Langmuir, 2000, 16, 10227.
134. Ricoul, F., Dubois, M., Belloni, L., Zemb, T., Andre-Barres, C., and Rico-Lattes, I., Langmuir, 1993, 14, 2645.
135. McIntosh, T. J., Curr. Opin. Struct. Biol., 2000, 10, 481, and references cited therein.
136. Robello, M. and Gliozzi, A., Biochim. Biophys. Acta, 1989, 982, 173.