Supra-molecular association and polymorphic behaviour in systems containing bile acid salts

Molecules

Volumn 12, Issue 8, 2007, Pages 1731-1754

  Calabresi, Marco ^a   Andreozzi, Patrizia ^a   La Mesa, Camillo ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

Bile salts; Fibres; Gels; Liquid crystals; Micelles; Solids; Solutions

Indexed keywords

BILE ACID;

CHEMISTRY; CONFORMATION; METABOLISM; MICELLE; REVIEW;

BILE ACIDS AND SALTS; MICELLES; MOLECULAR CONFORMATION;

EID: 34548403324     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/12081731     Document Type: Review

References (128)

1. Kullak-Ublick, G. A.; Stieger, B.; Hagenbuch, B; Meier, P. J. Hepatic transport of bile salts. Sem. Liver Dis. 2000, 20, 273-92.
2. Small, D.M. Role of ABC transporters in secretion of cholesterol from liver into bile. Proc. Nat. Acad. Sci. U.S.A.; 2003, 100, 4-6.
3. Small, D. M. Point mutations in the ileal bile salt transporter cause leaks in the enterohepatic circulation leading to severe chronic diarrhea and malabsorption. J. Clinical Invest. 1997, 99, 1807-1808.
4. Farthing, M. J. G.; Keusch, G. T.; Carey, M. C.; Varon, S. Effects of bile and bile salts on growth and membrane lipid uptake by Giardia lamblia. Possible implications for pathogenesis of intestinal disease. J. Clinical Invest. 1985, 76, 1727-32.
5. Sanchez-Mete L.; Attili, A. F. Cholelithiasis: genetic hypothesis. Minerva Gastroenterol. Dietol. 2000, 46, 45-55.
6. Van Erpecum, K. J.; Wang, D. Q.-H.; Lammert, F.; Paigen, B.; Groen, A. K.; Carey, M. C. Phenotypic characterization of Lith genes that determine susceptibility to cholesterol cholelithiasis in inbred mice: soluble pronucleating proteins in gallbladder and hepatic biles. J. Hepatol. 2001, 35, 444-451..
7. Small, D. M. Gallstones New Engl. J. Med. 1968, 279, 588-93.
8. Van Dyke, R. W.; Stephens, J. E.; Scharschmidt, B. F. Effects of ion substitution on bile acid-dependent and -independent bile formation by rat liver. J. Clinical Invest. 1982, 70, 505-17.
9. Siegfried, C. M.; Doisy, E. A. Jr; Elliott, W. H. Bile acids. XLIV, quantitation of bile acids from the bile fistula rat given (4-14C) cholesterol. Biochim. Biophys. Acta 1975, 380, 66-75.
10. Blossey, E. C.; Ford, W. T.; Periyasamy, M. Carbon-13 NMR spectra of multifunctional bile acid derivatives. Magn. Res. Chem. 1991, 29, 190-193.
11. Tobin, K. A. R.; Ulven, S. M.; Schuster, G. U.; Steineger, H. H.; Andresen S. M.; Gustafsson, J.-A.; Nebb, H. I. Liver X receptors as insulin-mediating factors in fatty acid and cholesterol biosynthesis. J. Biol. Chem. 2002, 277, 10691-10697.
12. Craven, P. A.; Pfanstiel, J.; De Rubertis, F. R. Role of reactive oxygen in bile salt stimulation of colonic epithelial proliferation. J. Clinical Invest. 1986, 77, 850-859.
13. Gonzalez, M. C.; Sutherland, E.; Simon, F. R. Regulation of hepatic transport of bile salt. Effect of protein synthesis inhibition on excretion of bile salts and their binding to liver surface membrane fractions. J. Clinical Invest. 1979, 63, 684-694.
14. Aubert, E.; Sbarra, V.; Le Petit-Thevenin, J.; Valette, A.; Lombardo, D. Site-directed Mutagenesis of the Basic N-terminal Cluster of Pancreatic Bile Salt-dependent Lipase. Functional significance. J. Biol. Chem. 2002, 277, 34987-34996.
15. Farruggia, B.; Pico, G. Role of electrostatic forces in hydroxy and keto bile salt-albumin interactions: some experimental observations. Gen. Physiol. Biophys. 1992, 11, 219-224.
16. Donovan, J. M.; Benedek, G. B.; Carey, M. C. Self-association of human apolipoproteins A-I and A-II and interactions of apolipoprotein A-I with bile salts: quasi-elastic light scattering studies. Biochemistry 1987, 26, 8116-8125.
17. Calcamuggi, G.; Lanzio, M.; Babini, G.; Martini, S.; Anfossi, G.; Emanuelli, G. Sodium taurocholate affects prostacyclin constitutive production by cultured human vascular endothelial cells. J. Labor. Clinical Med. 1990, 115, 756-760.
18. nd ed.; Pergamon Press: Cambridge, 1953.
19. Gee, J. M.; Johnson, I. T. Interactions between hemolytic saponins, bile salts and small intestinal mucosa in the rat. J. Nutr. 1988, 118, 1391-1397.
20. Sidhu, G. S.; Oakenfull, D. G. A mechanism for the hypocholesterolemic activity of saponins. British J. Nutr. 1986, 55, 643-649.
21. Donovan, J. M.; Jackson, A. A.; Carey, M. C. Molecular species composition of inter-mixed micellar/vesicular bile salt concentrations in model bile: dependence upon hydrophilichydrophobic balance. J. Lipid Res. 1993, 34, 1131-1140.
22. Schurtenberger, P.; Svård, M.; Wehrli, E.; Lindman, B. Vesicle formation in aqueous solutions of bile salt and monoacylglycerol. Biochim. Biophys.Acta, Gen. Sub. 1986, 882, 465-468.
23. Jones, E. L.; Nassimbeni, L. R. Crystal and molecular structures of the inclusion compounds of cholic acid with methanol, ethanol and 1-propanol. Acta Crystallogr. B 1990, 46, 399-405.
24. Yoswathananont, N.; Sada, K.; Miyata, M.; Akita, S.; Nakano, K. Dependence of selective enclathration on types of cholic acid crystals. Org. Biomol. Chem. 2003, 1, 210-214.
25. Small, D. M.; Dowling, R. H.; Redinger, R. N. Enterohepatic circulation of bile salts Arch. Intern. Med. 1972, 130, 552-573.
26. Redinger, R. N.; Small, D. M. Bile composition, bile salt metabolism, and gallstones Arch. Intern. Med. 1972, 130, 618-630.
27. Hofmann, A. F.; Small, D. M. Detergent properties of bile salts: correlation with physiological function. Ann. Rev. Med. 1967, 18, 333-376.
28. Ulmius, J.; Lindblom, G.; Wennerström, H.; Johansson, L. B.-Å, Fontell, K.; Söderman, O.; Arvidson, G. Molecular organization in the liquid-crystalline phases of lecithin-sodium cholate-water systems studied by nuclear magnetic resonance. Biochemistry 1982, 21, 1553-1560.
29. Small, D. M.; Physical chemistry of cholanic acids; In The Bile Acids, Nair, P. P.; Kritchevsky, D.; Eds.; Plenum Press: New York, 1971; Vol. I, Chapt. IV, pp. 249-356.
30. Cabral, D. J.; Hamilton, J.A.; Small, D. M. The ionization behavior of bile acids in different aqueous environments. J. Lipid Res. 1986, 27, 334-343.
31. D'Archivio, A. A.; Galantini, L.; Gavuzzo, E.; Giglio, E.; Scaramuzza, L. Possible Models for the Micellar Aggregates of Glycocholate and Taurocholate Salts from Crystal Structures, QELS, and CD Measurements. Langmuir 1996, 12, 4660-4667.
32. De Sanctis Candeloro, S.; D'Archivio, A. A.; Galantini, L.; Gavuzzo, E.; Giglio, E. On the role of hydronium ions in the protonated micellar aggregates of bile salts. Perkin 2 2000, 403-407.
33. Laughlin, R. G. The Aqueous Phase Behavior of Surfactants; Academic Press: San Diego, 1994.
34. Gu, J.; Hofmann, A. F.; Ton, N.; Huong T.; Schteingart, C. D.; Mysels, K. J. Solubility of calcium salts of unconjugated and conjugated natural bile acids. J. Lipid Res. 1992, 33, 635-646.
35. Hofmann, A. F.; Mysels, K. J. Bile acid solubility and precipitation in vitro and in vivo: the role of conjugation, pH, and Ca2+ ions. J. Lipid Res. 1992, 33, 617-626.
36. nd Ed.; Academic Press: New York, 1980.
37. Mukerjee, P.; Mysels, K. J. Critical Micelle Concentration of Aqueous Surfactant Systems; NSRDS, NBS: Washington, DC, 1971.
38. Shinoda, K.; Hutchinson, E. Pseudo-phase separation model for thermodynamic calculations on micellar solutions. J. Phys. Chem. 1958, 62, 577-582.
39. Stilbs, P. Fourier transform pulsed-gradient spin-echo studies of molecular diffusion. Prog. Nucl. Magn. Reson. Spectrosc. 1987, 19, 1-45.
40. Kratohvil, J. P.; Hsu, W. P.; Kwok, D. I. How large are the micelles of di-a-hydroxy bile salts at the critical micellization concentrations in aqueous electrolyte solutions? Results for sodium taurodeoxycholate and sodium deoxycholate. Langmuir 1986, 2, 256-258.
41. Roda, A.; Hofmann, A. F.; Mysels, K. J. The influence of bile salt structure on self-association in aqueous solutions. J. Biol. Chem. 1983, 258, 6362-6370.
42. van Os, N. M.; Haak, J. R.; Rupert, L. A. M. Physico-Chemical Properties of Selected Anionic, Cationic and Nonionic Surfactants; Elsevier: Amsterdam, 1993.
43. Ekwall, P. Concentration limits in association colloid solutions. J. Colloid Sci. 1954, Suppl.1, 66-80.
44. Desnoyers, J. E.; Caron, G.; De Lisi, R.; Roberts, D.; Roux, A.; Perron, G. Thermodynamic properties of alkyldimethylamine oxides in water. Application of a mass-action model for micellization. J. Phys. Chem. 1983, 87, 1397-1406.
45. Small, D. M. Size and structure of bile salt micelles. Influence of structure, concentration, counterion concentration, pH, and temperature. Adv. Chem. Ser. 1968, 84, 31-52.
46. Oakenfull, D. G.; Fisher, L. R. The role of hydrogen bonding in the formation of bile salt micelles. J. Phys. Chem. 1977, 81, 1838-1841.
47. Zana, R. The role of hydrogen bonding in the formation of bile salt micelles. Comments. J. Phys. Chem. 1978, 82, 2440-2443.
48. Oakenfull, D. G.; Fisher, L. R. The role of hydrogen bonding in the formation of bile salt micelles. Reply to comments. J. Phys. Chem. 1978, 82, 2443-2445.
49. Rajagopalan, N.; Vadnere, M.; Lindenbaum, S. Thermodynamics of aqueous bile salt solutions: heat capacity, enthalpy and entropy of dilution. J. Solution Chem. 1981, 10, 785-801.
50. Sugihara, G.; Yamakawa, K.; Murata, Y.; Tanaka, M. Effects of pH, pNa, and temperature on micelle formation and solubilization of cholesterol in aqueous solutions of bile salts. J. Phys. Chem. 1982, 86, 2784-2788.
51. Tanaka, M.; Kodera, Y.; Sugihara, G. Colloid chemistry of free bile salts. II. Recent information on mechanism of micelle formation. Fukuoka Daigaku Rigaku Shuho 1978, 8, 29-45.
52. Briganti, G.; D'Archivio, A. A.; Galantini, L.; Giglio, E. Structural Study of the Micellar Aggregates of Sodium and Rubidium Glyco- and Taurodeoxycholate. Langmuir 1996, 12, 1180-1187, and references therein.
53. Rich, A.; Blow, D. M. Formation of a helical steroid complex. Nature 1958, 182, 423-426.
54. D'Archivio, A. A.; Galantini, L.; Giglio, E. X-Ray, QELS, and CD Studies of the Micellar Aggregates of Calcium Taurodeoxycholate. Langmuir 1997, 13, 4197-4203.
55. Campanelli, A. R.; Candeloro De Sanctis, S.; Giglio, E.; Petriconi, S. The structure of helices of rubidium deoxycholate-water(3/10), 3(Rb+.C24H39O4-).10H2O. Acta Crystallogr. Sect. C 1984, 40, 631-635.
56. Campanelli, A. R.; Candeloro De Sanctis, S.; Giglio, E.; Scaramuzza, L. A model for micellar aggregates of a bile salt: crystal structure of sodium taurodeoxycholate monohydrate. J. Lipid Res. 1987, 28, 483-489.
57. Campanelli, A. R.; Candeloro DeSanctis, S.; Chiessi, E.; D'Alagni, M.; Giglio, E.; Scaramuzza, L. Sodium glyco- and taurodeoxycholate: possible helical models for conjugated bile salt micelles. J. Phys. Chem. 1989, 93, 1536-1542.
58. Campanelli, A. R.; Candeloro DeSanctis, S.; Galantini, L.; Giglio, E.; Scaramuzza, L. A possible helical model for sodium glycocholate micellar aggregates. J. Inclus. Phenom. Mol. Recognit. Chem. 1991, 10, 367-377.
59. Galantini, L.; Giglio, E.; La Mesa, C.; Pavel, N. V.; Punzo, F. Sodium Taurodeoxycholate Structure from Solid to Liquid Phase. Langmuir 2002, 18, 2812-2816.
60. Fontell, K. Micellar behavior in solutions of bile acid salts. III. Viscosity and density measurements in aqueous solutions. Koll. Z. u. Z. Polym. 1971, 246, 614-625.
61. Plowiec, R.; Kielczynski, P.; D'Arrigo, G.; La Mesa, C. Dynamic shear viscosity measurements in aqueous sodium deoxycholate solutions. Adv. Mol. Relax. Interact. Proc. 1982, 24, 181-189.
62. D'Arrigo, G.; La Mesa, C. Temperature and Concentration Effects on the Viscoelasticity of Concentrated Aqueous Solutions of Bile Salts in the Ultrasonic Range. Phys. Rev. A, 1981, 24, 2187-2190.
63. Sesta, B.; La Mesa, C.; Bonincontro, A.; Cametti, C.; Di Biasio, A. Molecular aggregation of sodium deoxycholate in water and water-urea mixtures; a multistep process. Ber. Bunsen. Phys. Chem. 1981, 85, 798-803.
64. Sesta, B.; La Mesa, C.; Bonincontro, A.; Cametti, C.; Di Biasio, A. Micellization processes in concentrated sodium deoxycholate solutions - effect of different counterions. Ber. Bunsen-Ges. Phys. Chem. 1982, 86, 664-670.
65. Mazer, N. A.; Kwasnick, R. F.; Carey, M. C.; Benedek, G. B.; Quasielastic light scattering spectroscopic studies of aqueous bile salt, bile salt-lecithin and bile salt-lecithin-cholesterol solutions. In Micellization, Solubilization, Microemulsions, Mittal, K. L.; Ed.; Plenum: New York, 1977; Vol. 1, pp. 383-402.
66. Mazer, N. A.; Carey, M. C.; Kwasnick, R. F.; Benedek, G. B. Quasielastic light scattering studies of aqueous biliary lipid systems. Size, shape, and thermodynamics of bile salt micelles. Biochemistry 1979, 18, 3064-3075.
67. Galantini, L.; Giglio, E.; Pavel, N. V.; Punzo, F. QELS and X-ray study of two dihydroxy bile salt aqueous solutions. Colloids Surf. A: Physicochem. Engineer. Asp. 2004, 248, 79-84.
68. Stark, R. E.; Gosselin, G. J.; Donovan, J. M.; Carey, M. C.; Roberts, M. F. Influence of dilution on the physical state of model bile systems: NMR and quasi-elastic light-scattering investigations. Biochemistry 1985, 24, 5599-605.
69. Hjelm, R. P.; Schteingart, C. D.; Hofmann, A. F.; Thiyagarajan, P. Structure of Conjugated Bile Salt-Fatty Acid-Monoglyceride Mixed Colloids: Studies by Small-Angle Neutron Scattering. J. Phys. Chem. B 2000, 104, 197-211.
70. Lindman, B. Micelles and microemulsions in ionic surfactant and bile salt systems studied by self-diffusion. Hepatology 1984, 4, 103S-109S.
71. Schurtenberger, P.; Lindman, B. Coexistence of simple and mixed bile salt-lecithin micelles: an NMR self-diffusion study. Biochemistry 1985, 24, 7161-7165.
72. D'Arrigo, G.; Sesta, B.; La Mesa, C. Evidence of viscoelastic effects in highly concentrated aqueous solutions of the bile salt sodium deoxycholate by ultrasonic measurements. J. Chem. Phys. 1980, 73, 4562-4568.
73. Berchiesi, G.; Berchiesi, M. A.; La Mesa, C.; Sesta, B. Static and dynamic studies on sodium taurodeoxycholate micellar aggregation in water in the range 25-45°C. J. Phys. Chem. 1984, 88, 3665-3669.
74. Bonincontro, A.; D'Archivio, A. A.; Galantini, L.; Giglio, E.; Punzo, F. X-ray, Electrolytic Conductance, and Dielectric Studies of Bile Salt Micellar Aggregates. Langmuir 2000, 16, 10436-10443.
75. Capalbi, A.; Gente, G.; La Mesa, C. Solution properties of alkyl glucosides, alkyl thioglucosides and alkyl maltosides. Colloids Surf. A: Physicochem. Eng. Asp. 2004, 246, 99-108.
76. Antonelli, M. L.; Capalbi, A.; Gente, G.; Palacios, A. C.; Sallustio, S.; La Mesa, C. Thermodynamic properties of the bovine serum albumin-sodium taurodeoxycholate system. Colloids Surf. A: Physicochem. Eng. Asp. 2004, 246, 127-134.
77. Palacios, A. C.; Antonelli, M. L.; La Mesa, C. Interactions between bovine serum albumin and sodium taurodeoxycholate: thermodynamic properties. Thermochim. Acta 2004, 418, 69-77.
78. Lydon, J. Chromonic liquid crystal phases. Curr. Opin. Colloid Interface Sci. 1998, 3, 455-466.
79. Small, D. M. Liquid crystals in living and dying systems. J. Colloid Interface Sci. 1977, 58, 581-602.
80. Edlund, H.; Khan, A.; La Mesa, C. Formation of a Liquid Crystalline Phase in the Water-Sodium Taurodeoxycholate System. Langmuir 1998, 14, 3691-3697.
81. Marques, E. F.; Edlund, H.; La Mesa, C.; Khan, A. Liquid Crystals and Phase Equilibria Binary Bile Salt-Water Systems. Langmuir 2000, 16, 5178-5186.
82. Amenitsch, H.; Edlund, H.; Khan, A.; Marques, E. F.; La Mesa, C. Bile salts form lyotropic liquid crystals. Colloids Surf. A: Physicochem. Eng. Asp. 2003, 213, 79-92.
83. La Mesa, C. A. Supra-molecular association in bile salts. Recent Res. Develop. Surf. Colloids 2004, 1, 97-115.
84. La Mesa, C.; Coppola, L. Krafft point solubility phenomena. Colloids Surf. 1989, 35, 325-328.
85. Rosevear, F. B. The microscopy of the liquid crystalline neat and middle phases of soaps and synthetic detergents. J. Am. Oil Chem. Soc. 1954, 31, 628-639.
86. Rosevear, F. B. Liquid crystals: the mesomorphic phases of surfactant compositions. J. Soc. Cosmet. Chem. 1968, 19, 581-594.
87. Ekwall, P. Composition, properties, and structures of liquid crystalline phases in systems of amphiphilic compounds. In Advances in Liquid Crystals; Brown, G. H.; Ed.; Academic Press: New York, 1975; Vol. I, pp. 1-142.
88. Luzzati, V.; Mustacchi, H.; Skoulios, A.E. Husson, F. The structure of association colloids. I. The liquid-crystalline phases of the amphiphile-water system. Acta Crystallogr. 1960, 13, 660-667.
89. Fontell, K. Liquid crystallinity in lipid-water systems. Mol. Cryst. Liq. Cryst. 1982, 63, 59-82.
90. Lindman, B.; Söderman, O.; Wennerström, H.; NMR studies of surfactant systems. In: Surfactant Solutions. New Methods of Investigation; Zana, R.; Ed.; Marcel Dekker: New York, 1986; Chap. VI, pp. 295-357.
91. Khan, A.; Fontell, K.; Lindblom, G.; Lindman, B. Liquid crystallinity in a calcium surfactant system. Phase equilibriums and phase structures in the system calcium octyl sulfate/decan-1-ol/water. J. Phys Chem. 1982, 86, 4266-4271.
92. Marques, E.; Khan, A.; Miguel, M. G.; Lindman, B. Self-assembly in mixtures of a cationic and an anionic surfactant: the sodium dodecyl sulfate-didodecyldimethylammonium bromide-water system. J. Phys. Chem. 1993, 97, 4729-4736.
93. Tiddy, G. J. T. Surfactant-water liquid crystal phases. Phys. Rep. 1980, 57, 1-46.
94. Khan, A.; Jönsson, B.; Wennerström, H. Phase equilibria in the mixed sodium and calcium di-2-ethylhexylsulfosuccinate aqueous system. An illustration of repulsive and attractive double-layer forces. J. Phys. Chem. 1985, 89, 5180-5184.
95. Larsson, K. Lipids - Molecular Organisation, Physical Functions and Technical Applications; The Oily Press: Dundee, 1994.
96. Hofmann, A. F. Micellar solubilization of fatty acids and monoglycerides by bile salt solutions. Nature 1961, 190, 1106-1107.
97. Jones, C. A.; Hofmann, A. F.; Mysels, K. J.; Roda, A. The effect of calcium and sodium ion concentration on the properties of dilute aqueous solutions of glycine conjugated bile salts: phase behavior and solubility products of the calcium salts of the common glycine conjugated bile acids. J. Colloid Interface Sci. 1986, 114, 452-470.
98. Small, D. M.; Bourges, M.; Dervichian, D. G. Ternary and quaternary aqueous systems containing bile salt, lecithin, and cholesterol. Nature 1966, 211, 816-818.
99. Small, D. M.; Bourges, M.; Dervichian, D. G. The biophysics of lipidic associations. I. The ternary systems: lecithin-bile salt-water. Biochim. Biophys. Acta, Lip. Lipid Metabol. 1966, 125, 563-580.
100. Small, D. M.; Bourges, M. Lyotropic paracrystalline phases obtained with ternary and quaternary systems of amphiphilic substances in water: Studies on aqueous systems of lecithin, bile salt, and cholesterol. Mol. Cryst. 1966, 1, 541-561.
101. Bourges, M.; Small, D. M.; Dervichian, D. G. Biophysics of lipid associations. III. Quaternary systems lecithin-bile salt-cholesterol-water. Biochim. Biophys. Acta, Lip. Lipid Metabol. 1967, 144, 189-201.
102. Fisher, L.; Oakenfull, D. The environment of solubilized molecules in bile salt micelles. Aust. J. Chem. 1979, 32, 31-39.
103. Fontell, K. Micellar behavior in solutions of bile acid salts. Koll. Z. u. Z. Polym. 1972, 250, 333-343.
104. Hay, D.W.; Cahalane, M. J.; Timofeyeva, N.; Carey, M. C. Molecular species of lecithins in human gallbladder bile. J. Lipid Res. 1993, 34, 759-768.
105. Fontell, K. Micellar behavior in solutions of bile acid salts. VI. Solutions of the three-component system bile acid salt, n-decanol, and water. Koll. Z. u. Z. Polym. 1972, 250, 825-835.
106. Jönsson, B.; Wennerström, H. Phase equilibria in a three-component water-soap-alcohol system. A thermodynamic model. J. Phys. Chem. 1987, 91, 338-352.
107. La Mesa, C.; Khan, A.; Fontell, K.; Lindman, B. Phase diagrams and NMR studies of some ternary sodium deoxycholate-surfactant-water systems. J. Colloid Interface Sci. 1985, 103, 373-391.
108. Swanson-Vethamuthu, M.; Almgren, M.; Bergenståhl, B.; Mukhtar, E. The hexagonal phase and cylindrical micelles in the system alkyltrimethylammonium bromide-sodium desoxycholate-water as studied by x-ray diffraction and fluorescence quenching. J. Colloid Interface Sci. 1996, 178, 538-548.
109. Svärd, M.; Schurtenberger, P.; Fontell, K.; Jönsson, B.; Lindman, B. Micelles, vesicles, and liquid crystals in the monoolein-sodium taurocholate-water system: phase behavior, NMR, selfdiffusion, and quasi-elastic light scattering studies. J. Phys. Chem. 1988, 92, 2261-2270.
110. Marques, E. F.; Regev, O.; Edlund, H.; Khan, A. Micelles, Dispersions, and Liquid Crystals in the Catanionic Mixture Bile Salt-Double-Chained Surfactant. The Bile Salt-Rich Area. Langmuir 2000, 16, 8255-8262.
111. Szebeni, J.; Baranyi, L.; Savay, S.; Milosevits, J.; Bunger, R.; Laverman, P.; Metselaar, J.; Storm, G.; Chanan-Khan, A.; Liebes, L.; Muggia, F. M.; Cohen, R.; Barenholz, Y. Role of complement activation in hypersensitivity reactions to doxil and HYNIC PEG liposomes: experimental and clinical studies. J. Liposome Res. 2002, 12, 165-172.
112. Coppola, L.; private communication.
113. Orioni, B.; Roversi, M.; La Mesa, C.; Asaro, F.; Pellizer, D'Errico, G. Polymorphic Behavior in Protein-Surfactant Mixtures: The Water-Bovine Serum Albumin-Sodium Taurodeoxycholate System. J. Phys. Chem. B 2006, 110, 12129-12140.
114. Palacios, A. C.; Sarnthein-Graf, C.; La Mesa, C. Equilibrium between phases in water-protein-surfactant systems. Colloids Surf. A, Physicochem. Engineer. Asp. 2003, 228, 25-35.
115. Scagnolari, F.; Roda, A.; Fini, A.; Grigolo, B. Thermodynamic features of bile salt-human serum albumin interaction. Biochim. Biophys. Acta, Protein Struct. Mol. Enzymol. 1984, 791, 274-277.
116. Nakamura, K.; Era, S.; Ozaki, Y.; Sogami, M.; Hayashi, T.; Muratami, M. Conformational changes in seventeen cystine disulfide bridges of bovine serum albumin proved by Raman spectroscopy. FEBS Lett. 1997, 417, 375-378.
117. Ferre, M. L.; Duchowicz, R.; Carrasco, B.; Garcia de la Torre, J.; Acuna, A. U. The conformation of serum albumin in solution: a combined phosphorescence depolarization-hydrodynamic modeling study. Biophys. J. 2001, 80, 2422-2430.
118. Moren, A. K.; Khan, A. Phase Equilibria of an anionic surfactant (Sodium Dodecyl Sulfate) and an Oppositely Charged Protein (Lysozyme) in Water. Langmuir 1995, 11, 3636-3643.
119. Moren, A. K.; Khan, A. Surfactant Hydrophobic Effect on the Phase Behavior of Oppositely Charged Protein and Surfactant Mixtures: Lysozyme and Sodium Alkyl Sulfates. Langmuir 1998, 14, 6818-6826.
120. Sesta, B.; Gente, G.; Iovino, A.; Laureti, F.; Michiotti, P.; Paiusco, O.; Palacios, A. C.; Persi, L.; Princi, A.; Sallustio, S.; Sarnthein-Graf, C.; Capalbi, A.; La Mesa, C. Supramolecular Association in the System Water-Lysozyme-Lithium Perfluorononanoate. J. Phys. Chem. B 2004, 108, 3036-3043.
121. Roversi, M.; La Mesa, C. Rheological properties of protein-surfactant based gels. J. Colloid Interface Sci. 2005, 284, 470-476.
122. Aldini, R.; Montagnani, M.; Roda, A.; Hrelia, S.; Biagi, P. L.; Roda, E. Intestinal absorption of bile acids in the rabbit: different transport rates in jejunum and ileum. Gastroenterology 1996, 110, 459-468.
123. Calabresi, M.; La Mesa, C. Manuscript in preparation.
124. Fletcher, P. D. I.; Robinson, B. H. Freedman, R. B. Oldfield, C. Activity of lipase in water-in-oil microemulsions. J. Chem Soc. Faraday Trans. 1985, 81, 2667-2679.
125. Waldmann, T. A. in: Albumin: Structure, Function and Uses; Rosenoer, V. M.; Oratz, M.; Rothschild, M. A.; Eds; Pergamon: Oxford, 1977; p. 255.
126. Boye, J. J.; Inteaz, A.; Ismail, A.A. Interactions Involved in the Gelation of Bovine Serum Albumin J. Agr. Food Chem. 1996, 44, 996-1004.
127. Stenstam, A.; Montalvo, G.; Grillo, I.; Gradzielski, M. Small Angle Neutron Scattering Study of Lysozyme-Sodium Dodecyl Sulfate Aggregates. J. Phys. Chem. B 2003, 107, 12331-12338.
128. La Mesa, C. Polymer-surfactant and protein-surfactant interactions. J. Colloid Interface Sci. 2005, 286, 148-157.