Kinetic and equilibrium studies of bile salt–liposome interactions

References

• Albalak A, Zeidel ML, Zucker SD, et al. (1996). Effects of submicellar bile salt concentrations on biological membrane permeability to low molecular weight non-ionic solutes. Biochemistry 35:7936–45
   PubMedGoogle Scholar
• Angeletti C, Wylie Nichols J. (1998). Dithionite quenching rate measurement of the inside-outside membrane bilayer distribution of 7-nitrobenz-2-oxa-1,3-diazol-4-yl-labeled phospholipid. Biochemistry 37:15114–19
   Google Scholar
• Annesini MC, Memoli A, Petralito S. (2000). Kinetics of surfactant-induced release from liposomes: a time-dependent permeability model. J Membr Sci 180:121–31
   Google Scholar
• Armstrong VT, Brzustowicz MR, Wassall SR, et al. (2003). Rapid flip-flop in polyunsaturated (docosahexaenoate) phospholipid membranes. Arch Biochem Biophys 414:74–82
   PubMed Web of Science ®Google Scholar
• Avdeef A, Box KJ, Comer JEA, et al. (1998). pH-Metric logP. Determination of liposomal membrane-water partition coefficients of ionizable drugs. Pharm Res 15:209–15
   PubMed Web of Science ®Google Scholar
• Carey MC. (1985). Physico-chemical properties of bile acids and their salts. In: Danielsson H, Sjövall J, eds. Sterols and bile acids. 1st ed. Amsterdam: Elsevier, 345–403
   Google Scholar
• Chen G, Yang L, Zhang H, et al. (2012). Effect of ketocholate derivatives on methotrexate uptake in Caco-2 cell monolayers. Int J Pharm 433:89–93
   Google Scholar
• Chen X, Oshima T, Tomita T, et al. (2011). Acidic bile salts modulate the squamous epithelial barrier function by modulating tight junction proteins. Am J Physiol Gastrointest Liver Physiol 301:G203–9
   Google Scholar
• Dai Y, Zhou R, Liu L, et al. (2013). Liposomes containing bile salts as novel ocular delivery systems for tacrolimus (FK506): in vitro characterization and improved corneal permeation. Int J Nanomed 8:1921–33
   PubMed Web of Science ®Google Scholar
• Donovan JM, Jackson AA. (1997). Transbilayer movement of fully ionized taurine-conjugated bile salts depends upon bile salt concentration, hydrophobicity, and membrane cholesterol content. Biochemistry 36:11444–51
   PubMed Web of Science ®Google Scholar
• Elsayed MMA, Cevc G. (2011). The vesicle-to-micelle transformation of phospholipid-cholate mixed aggregates: a state of the art analysis including membrane curvature effects. Biochim Biophys Acta 1808:140–53
   PubMed Web of Science ®Google Scholar
• Fahey DA, Carey MC, Donovan JM. (1995). Bile acid/phosphatidylcholine interactions in mixed monomolecular layers: differences in condensation effects but not interfacial orientation between hydrophobic and hydrophilic bile acid species. Biochemistry 34:10886–97
   Google Scholar
• Gordon GS, Moses AC, Silver RD, et al. (1985). Nasal absorption of insulin: enhancement by hydrophobic bile salts. Proc Natl Acad Sci USA 82:7419–23
   PubMed Web of Science ®Google Scholar
• Gubernator J, Stasiuk M, Kosubek A. (1999). Dual effect of alkylresorcinols, natural amphiphilic compounds, upon liposomal permeability. Biochim Biophys Acta 1418:253–60
   Google Scholar
• Heerklotz H. (2001). Membrane stress and permeabilization induced by asymmetric incorporation of compounds. Biophys J 81:184–95
   Google Scholar
• Heerklotz H, Seelig J. (2000). Correlation of the membrane/water partition coefficients of detergents with the critical micelle concentration. Biophys J 78:2435–40
   PubMed Web of Science ®Google Scholar
• Hildebrand A, Neubert R, Garidel P, Blume A. (2002). Bile salt induced solubilization of synthetic phosphatidylcholine vesicles studied by isothermal titration calorimetry. Langmuir 18:2836–47
   Web of Science ®Google Scholar
• Hinow P, Radunskaya A, Tucker I, Yang L. (2012). Kinetics of bile salt binding to liposomes revealed by carboxyfluorescein release and mathematical modeling. J Liposome Res 22:237–44
   PubMed Web of Science ®Google Scholar
• Hu S, Niu M, Hu F, et al. (2013). Integrity and stability of oral liposomes containing bile salts studied in simulated and ex vivo gastrointestinal media. Int J Pharm 441:693–700
   PubMed Web of Science ®Google Scholar
• Hunter RJ. (2001). Foundations of colloid science. 2nd ed. Chapter 7. Oxford, UK:Oxford University Press
   Google Scholar
• In't Veld G, Driessen AJ, Op den Kamp JA, Konings WN. (1991). Hydrophobic membrane thickness and lipid-protein interactions of the leucine transport system of Lactococcus lactis. Biochim Biophys Acta 1065:203–12
   Google Scholar
• Kamp F, Hamilton JA. (1993). Movement of fatty acids, fatty acid analogues, and bile acids across phospholipid bilayers. Biochemistry 32:11074–86
   PubMedGoogle Scholar
• Krämer SD, Jakits-Deiser C, Wunderli-Allenspach H. (1997). Free fatty acids cause pH-dependent changes in drug-lipid membrane interactions around physiological pH. Pharm Res 14:827–32
   PubMed Web of Science ®Google Scholar
• Lichtenberg D, Ahyayauch H, Goñi FM. (2013). The mechanism of detergent solubilization of lipid bilayers. Biophys J 105:289–99
   PubMed Web of Science ®Google Scholar
• Lin CM, Chang GP, Tsao HK, Sheng YJ. (2011). Solubilization mechanism of vesicles by surfactants: effect of hydrophobicity. J Chem Phys 135:045102 (1–10)
   Google Scholar
• Liu J, Conboy JC. (2005). 1,2-Diacyl-phosphatidylcholine flip-flop measured directly by sum-frequency vibrational spectroscopy. Biophys J 89:2522–32
   PubMed Web of Science ®Google Scholar
• Luk AS, Kaler EW, Lee SP. (1997). Structural mechanisms of bile salt-induced growth of small unilamellar cholesterol-lecithin vesicles. Biochemistry 36:5633–44
   Google Scholar
• Matsuzaki K, Murase O, Fujii ND, Miyajima K. (1996). An antimicrobial peptide, magainin 2, induced rapid flip-flop of phospholipids coupled with pore formation and peptide translocation. Biochemistry 35:11361–8
   PubMed Web of Science ®Google Scholar
• McIntyre JC, Sleight RG. (1991). Fluorescence assay for phospholipid membrane asymmetry. Biochemistry 30:11819–27
   PubMed Web of Science ®Google Scholar
• Memoli A, Annesini MC, Petralito S. (1999). Surfactant-induced leakage from liposomes: a comparison among different lecithin vesicles. Int J Pharm 184:227–35
   PubMed Web of Science ®Google Scholar
• Mikov M, Fawcett JP, Kuhajda K, Kevresan S. (2006). Pharmacology of bile acids and their derivatives. Eur J Drug Metab Pharmacokinet 31:237–516
   PubMed Web of Science ®Google Scholar
• Mikov M, Kevresan S, Kuhajda K, et al. (2004). 3Alpha,7alpha-dihydroxy-12-oxo-5beta-cholanate as blood-brain barrier permeator. Pol J Pharmacol 56:367–71
   PubMedGoogle Scholar
• Moreno MJ, Estronca LMBB, Vaz WLC. (2006). Translocation of phospholipids and dithionite permeability in liquid-ordered and liquid-disordered membranes. Biophys J 91:873–81
   PubMed Web of Science ®Google Scholar
• Morimoto K, Nakai T, Morisaka K. (1987). Evaluation of permeability enhancement of hydrophilic compounds and macromolecular compounds by bile salts through rabbit corneas in-vitro. J Pharm Pharmacol 39:124–6
   PubMed Web of Science ®Google Scholar
• Naveen C, Kiran Kumar Y, Venkateshwar Rao P, Rama Rao T. (2011). Chemical enhancers in buccal and sublingual delivery. Int J Pharm Sci Nanotech 4:1307–19
   Google Scholar
• O'Connor CJ, Wallace RG, Iwamoto K. (1985). Bile salt damage of egg phosphatidylcholine liposomes. Biochim Biophys Acta 817:95–102
   PubMed Web of Science ®Google Scholar
• Raimondi F, Santori P, Barone MV, et al. (2008). Bile acids modulate tight junction structure and barrier function of Caco-2 monolayers. Am J Physiol Gastrointest Liver Physiol 294:G906–13
   PubMed Web of Science ®Google Scholar
• Rowland RN, Woodley JF. (1980). The stability of liposomes in vitro to pH, bile salts and pancreatic lipase. Biochim Biophys Acta 620:400–9
   PubMed Web of Science ®Google Scholar
• Schubert R, Jaroni H, Schoelmerich J, Schmidt KH. (1983). Studies on the mechanism of bile salt-induced liposomal membrane damage. Digestion 28:181–90
   PubMed Web of Science ®Google Scholar
• Schubert R, Schmidt KH. (1988). Structural changes in vesicle membranes and mixed micelles of various lipid compositions after binding of different bile salts. Biochemistry 27:8787–94
   PubMed Web of Science ®Google Scholar
• Spigelman MK, Zappula RA, Malis LI, et al. (1983). Intracarotid dehydrocholate infusion: a new method for prolonged reversible blood brain barrier disruption. Neurosurgery 12:606–12
   PubMed Web of Science ®Google Scholar
• van Blitterswijk WJ, van der Meer BW, Hilkmann H. (1987). Quantitative contributions of cholesterol and the individual classes of phospholipids and their degree of fatty acyl (un)saturation to membrane fluidity measured by fluorescence polarization. Biochemistry 26:1746–56
   PubMedGoogle Scholar
• Yang L, Fawcett JP, Østergaard J, et al. (2012). Mechanistic studies of the effect of bile salts on rhodamine 123 uptake into RBE4 cells. Mol Pharm 9:29–36
   PubMed Web of Science ®Google Scholar
• Yang L, Zhang H, Mikov M, Tucker IG. (2009). Physicochemical and biological characterization of monoketocholic acid, a novel permeability enhancer. Mol Pharm 6:448–56
   PubMed Web of Science ®Google Scholar