Solubilization of lipid bilayers by myristyl sucrose ester: effect of cholesterol and phospholipid head group size

Chemistry and Physics of Lipids

Volumn 157, Issue 2, 2009, Pages 104-112

  Toro, C ^a   Sanchez, S A ^b   Zanocco, A ^a   Lemp, E ^a   Gratton, E ^b   Gunther, G ^a  

^a UNIVERSITY OF CHILE   (Chile)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Cholesterol; DODAC; Liposomes; POPC; Solubilization; Sucrose ester; Vesicles

Indexed keywords

2 OLEOYL 1 PALMITOYLPHOSPHATIDYLCHOLINE; AMMONIUM CHLORIDE; BETA DEXTRO FRUCTOFURANOSYL 6 O MYRISTYL ALPHA DEXTRO GLUCOPYRANOSIDE; CHOLESTEROL; DIOCTADECYLDIMETHYLAMMONIUM CHLORIDE; LIPOSOME; PHOSPHOLIPID; SUCROSE ESTER DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CONTROLLED STUDY; LIPID ANALYSIS; LIPID BILAYER; MEMBRANE STRUCTURE; MOLECULAR DYNAMICS; PRIORITY JOURNAL; SOLUBILIZATION;

2-NAPHTHYLAMINE; CHOLESTEROL; DETERGENTS; KINETICS; LAURATES; LIPID BILAYERS; LIPOSOMES; MYRISTIC ACID; PHOSPHATIDYLCHOLINES; PHOSPHOLIPIDS; QUATERNARY AMMONIUM COMPOUNDS; SOLUBILITY; SPECTROMETRY, FLUORESCENCE;

EID: 58149477463     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2008.11.004     Document Type: Article

References (56)

1. Ahmed S.N., Brown D.A., and London E. On the origin of sphingolipid/cholesterol-rich detergent-insoluble cell membranes: physiological concentrations of cholesterol and sphingolipid induce formation of a detergent-insoluble, liquid-ordered lipid phase in model membranes. Biochemistry 36 (1997) 10944-10953
2. Almog S., Litman B.J., Wimley W., Cohen J., Wachtel E.J., Barenholz Y., Benshaul A., and Lichtenberg D. States of aggregation and phase-transformations in mixtures of phosphatidylcholine and octyl glucoside. Biochemistry 29 (1990) 4582-4592
3. Angelova M.I., and Dimitrov D.S. Liposome electroformation. Faraday Discuss. Chem. Soc. 81 (1986) 303-311
4. Becerra N., de la Nuez L.R., Zanocco A.L., Lemp E., and Gunther G. Solubilization of dodac small unilamellar vesicles by sucrose esters-a fluorescence study. Colloid Surf. A 272 (2006) 2-7
5. Brown D.A., and Rose J.K. Sorting of GPI-anchored proteins to glycolipid-enriched membrane subdomains during transport to the apical cell-surface. Cell 68 (1992) 533-544
6. Carmona-Ribeiro A.M., and Chaimovich H. Salt-Induced aggregation and fusion of dioctadecyldimeethylammonium chloride and sodium dihexadecylphosphate vesicles. Biophys. J. 50 (1986) 621-628
7. Cocera M., Lopez O., Coderch L., Parra J.L., and de la Maza A. Sublytic alterations caused by the nonionic surfactant dodecyl maltoside in stratum corneum lipid liposomes. Langmuir 18 (2002) 297-300
8. Chern C.S., Chiu H.C., and Yang Y.S. Interactions between nonionic Triton X surfactants and cholesterol-containing phosphatidylcholine liposomes. J. Colloid Interface Sci. 302 (2006) 335-340
9. de la Maza A., and Parra J.L. Disintegration liposomes by anionic surfactants and formation mixed micelles. Langmuir 9 (1993) 870-873
10. de la Maza A., and Parra J.L. Solubilization of phospholipid bilayer caused by surfactants. J. Am. Oil Chem. Soc. 70 (1993) 699-706
11. Deo N., and Somasundaran P. Disintegration of liposomes by surfactants: mechanism of protein and cholesterol effects. Langmuir 19 (2003) 2007-2012
12. Deo N., Somasundaran P., and Itagaki Y. Mechanisms of solubilization of mixed liposomes: preferential dissolution of liposome components. Ind. Eng. Chem. Res. 44 (2005) 1181-1186
13. El Kirat K., and Morandat S. Cholesterol modulation of membrane resistance to Triton X-100 explored by atomic force microscopy. Biochim. Biophys. Acta Biomembr. 1768 (2007) 2300-2309
14. Encinas M.V., Lemp E., and Lissi E.A. Vesicular effect on the reactivity of anthracene-derivatives towards singlet molecular-oxygen. J. Photochem. Photobiol. B: Biol. 3 (1989) 113-122
15. 4 and alcohol systems. J. Colloid Interface Sci. 273 (2004) 638-644
16. Harris F.M., Best K.B., and Bell J.D. Use of Laurdan fluorescence intensity and polarization to distinguish between changes in membrane fluidity and phospholipid order. BBA 1565 (2002) 123-128
17. 6 between lipid-detergent mixed membranes and water by means of Laurdan Fluorescence Spectroscopy. J. Fluoresc. 4 (1994) 319-352
18. Helenius A., and Simons K. Solubilization of membranes by detergents. Biochim. Biophys. Acta 415 (1975) 29-79
19. Inoue T., Muraoka Y., Fukushima K., and Shimozawa R. Interaction of surfactants with vesicle membrane of dipalmitoylphosphatidylcholine-fluorescence depolarization study. Chem. Phys. Lip. 46 (1988) 107-115
20. Jackson M.L., Schmidt C.F., Lichtenberg D., Litman B.J., and Albert A.D. Solubilization of phosphatidilcholine by octyl glucoside. Biochemistry 21 (1982) 4576-4582
21. Koynova R., and Caffrey M. Phases and phase transitions of the phosphatidylcholines. Biochim. Biophys. Acta: Rev. Biomembr. 1376 (1998) 91-145
22. Kragh-Hansen U., le Maire M., and Möller J.V. The mechanism of detergent solubilization of liposomes and protein-containing membranes. Biophys. J. 75 (1998) 2932
23. Lemp E., Zanocco A.L., and Gunther G. Structural changes in DODAC unilamellar liposomes by addition of sucrose esters monitored by using fluorescent techniques. Colloid Surf. A 229 (2003) 63-73
24. Lichtenberg D. Characterization of the solubilization of lipid bilayers by surfactants. BBA 821 (1985) 470-478
25. Lichtenberg D., Goni F.M., and Heerklotz H. Detergent-resistant membranes should not be identified with membrane rafts. Trends Biochem. Sci. 30 (2005) 430-436
26. Lissi E.A., Abuin E., Saez M., Zanocco A., and Disalvo A. Anomalous dependence of pyrene spectra and lifetimes with temperature in large unilamellar vesicles from dioctadecyldimethylammonium chloride and dipalmitoylphosphatidylcholine. Langmuir 8 (1992) 348-350
27. Lopez O., Walther P., Cocera M., de la Maza A., Coderch L., and Parra J.L. Structural modifications in the stratum corneum by effect of different solubilizing agents: a study based on high-resolution low-temperature scanning electron microscopy. Skin Pharmacol. App. Skin Phys. 13 (2000) 265-272
28. Lopez O., Cocera M., Parra J.L., and de la Maza A. Solubilization of stratum corneum lipid liposomes by C-14-betain/sodium dodecyl sulfate mixtures. Influence of the level of ceramides in the solubilization process. Colloid Surf. A 162 (2000) 131-140
29. Lopez O., Cocera M., Walther P., de la Maza A., Coderch L., and Parra J.L. Octyl glucoside as a tool to induce structural modifications in the stratum corneum. Colloid Surf. A 168 (2000) 115-123
30. Lopez O., Cocera M., Parra J.L., and de la Maza A. Influence of the hydrophobic tail of alkyl glucosides on their ability to solubilize stratum corneum lipid liposomes. Colloid Polym. Sci. 279 (2001) 909-915
31. Lopez O., Cocera M., Parra J.L., and de la Maza A. Influence of the alkyl chain length of alkyl glucosides on their ability to solubilize phosphatidylcholine liposomes. Colloid Surf. A 193 (2001) 221-229
32. Lopez O., Cocera M., Lopez-Iglesias C., Walter P., Coderch L., Parra J.L., and de la Maza A. Reconstitution of liposomes inside the intercellular lipid domain of the stratum corneum. Langmuir 18 (2002) 7002-7008
33. Melchior D.L., Scavitto F.J., and Steim J.M. Dilatometry of dipalmitoyllecithin-cholesterol bilayers. Biochemistry 19 (1980) 4828-4834
34. Munro S. Lipid rafts: ellusive or illusive?. Cell 115 (2003) 377-388
35. Nascimento D.B., Rapuano R., Lessa M.M., and Carmona-Ribeiro A.M. Counterion effects on properties of cationic vesicles. Langmuir 14 (1998) 7387-7391
36. Needham D., McIntosh T.J., and Evans E. Thermomechanical and transition properties of dimyristoylphosphatidylcholine cholesterol bilayers. Biochemistry 27 (1988) 4668-4673
37. Nemeczt G., and Schroeder F. Time-resolved fluorescence investigation membrane cholesterol heterogeneity and exchange. Biochemistry 27 (1988) 7740-7749
38. Ollivon M., Eidelman O., Blumenthal R., and Walter A. Micelle-vesicle transition of egg phosphatidylcholine and octyl glucoside. Biochemistry 27 (1988) 1695-1703
39. Osipow L., Snell F.D., York W.C., and Finchler A. Methods of preparation of fatty acid esters of sucrose. Ind. Eng. Chem. 48 (1956) 1459
40. Parasassi T., De Stasio G., Ravagnan G., Rusch R.M., and Gratton E. Quantitation of lipid phases in phospholipid vesicles by the generalized polarization of LAURDAN fluorescence. Biophys. J. 60 (1991) 179-189
41. Parasassi T., Krasnowska E.K., Bagatolli L., and Gratton E. Laurdan and Prodan as polarity-sensitive fluorescent membrane probes. J. Fluoresc. 8 (1998) 365-373
42. Paternostre M., Meyer O., GrabielleMadelmont C., Lesieur S., Ghanam M., and Ollivon M. Partition coefficient of a surfactant between aggregates and solution: Application to the micelle-vesicle transition of egg phosphatidylcholine and octyl beta-d-glucopyranoside. Biophys. J. 69 (1995) 2476-2488
43. Paternostre M.T., Roux M., and Rigaud J.L. Mechanisms of membrane-protein insertion into liposomes during reconstitution procedures involving the use of detergents. 1. Solubilization of large unilamellar liposomes (prepared by reverse-phase evaporation) by Triton X-100, octyl glucoside, and sodium cholate. Biochemistry 27 (1988) 2668-2677
44. Pike L.J. Growth factor receptors, lipid rafts and caveolae: an evolving story. BBA 1476 (2005) 260-273
45. Pike L.J. Rafts defined: a report on the keystone symposium on lipids rafts and cell function. J. Lipid Res. 47 (2006) 1597-1598
46. Rawicz W., Olbrich K.C., McIntosh T., Needham D., and Evans E. Effect of chain length and unsaturation on elasticity of lipid bilayers. Biophys. J. 79 (2000) 328-339
47. Sanchez S.A., Bagatolli L.A., Gratton E., and Hazlett T.L. A two-photon view of an enzyme at work: Crotalus atrox venom PLA(2) interaction with single-lipid and mixed-lipid giant unilamellar vesicles. Biophys. J. 82 (2002) 2232-2243
48. Schnitzer E., Kozlov M.M., and Lichtenberg D. The effect of cholesterol on the solubilization of phosphatidylcholine bilayers by the non-ionic surfactant Triton X-100. Chem. Phys. Lipids 135 (2005) 69-82
49. So P.T.C., French T., Yu W.M., Berland K.M., Dong C.Y., and Gratton E. Time resolved fluorescence microscopy using two photon excitation. Bioimaging 3 (1995) 49-63
50. Sot J., Collado M.I., Arrondo J.L.R., Alonso A., and Goni F.M. Triton X-100-resistant bilayers: effect of lipid composition and relevance to the raft phenomenon. Langmuir 18 (2002) 2828-2835
51. Thewalt J.L., and Bloom M. Phosphatidylcholine-cholesterol phase-diagrams. Biophys. J. 63 (1992) 1176-1181
52. Vlahov I.R., Vlahova P.I., and Lindhart R.J. Regioselective synthesis of sucrose monoesters as surfactants. J. Carbohyd. Chem. 16 (1997) 1-10
53. Williams E.E., Cooper J.A., Stillwell W., and Jenski L.J. The curvature and cholesterol content of phospholipid bilayers alter the transbilayer distribution of specific molecular species of phosphatidylethanolamine. Mol. Membr. Biol. 17 (2000) 157-164
54. Yakushi T., Kojima M., and Homma K. Isolation of Vibrio alginolyticus sodium-driven flagellar motor complex composed PomA and PomB solubilized by sucrose monocaprate. Microbiology-Sgm 150 (2004) 911-920
55. York W.C., Finchler A., Osipow L., and Snell F.D. Structural studies on sucrose monolaurate. J. Am. Oil Chem. Soc. 33 (1956) 424
56. Zidovetzki R., and Levitan I. Use of cyclodextrins to manipulate plasma membrane cholesterol content: evidence, misconceptions and control strategies. BBA 1768 (2007) 1311-1324