Sterol chemical configuration influences the thermotropic phase behaviour of dipalmitoylphosphatidylcholine bilayers containing 5α-cholestan- 3β- and 3α-ol

Chemistry and Physics of Lipids

Volumn 164, Issue 1, 2011, Pages 62-69

  Benesch, Matthew G K ^a   Mannock, David A ^a   McElhaney, Ronald N ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Cholestanol; Cholesterol; Differential scanning calorimetry; Dihydrocholesterol; Epicholestanol; Phase behaviour; Phosphatidylcholine; Sterol lipid interactions

Indexed keywords

5ALPHA CHOLESTAN 3ALPHA OL; CHOLESTANOL; DIPALMITOYLPHOSPHATIDYLCHOLINE; EPICHOLESTEROL; FUNCTIONAL GROUP; STEROL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CONCENTRATION RESPONSE; CONFORMATION; DIFFERENTIAL SCANNING CALORIMETRY; ENTHALPY; GEL; LIPID BILAYER; LIQUID CRYSTAL; MISCIBILITY; MOLECULAR STABILITY; PHASE TRANSITION; PHOSPHOLIPID BILAYER; PRIORITY JOURNAL;

1,2-DIPALMITOYLPHOSPHATIDYLCHOLINE; CALORIMETRY, DIFFERENTIAL SCANNING; CHOLESTANOL; ISOMERISM; LIPID BILAYERS; MOLECULAR CONFORMATION; PHASE TRANSITION; TEMPERATURE; THERMODYNAMICS;

EID: 78650294212     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2010.10.003     Document Type: Article

References (45)

1. C-H interactions, anomeric effects. What is really important? J. Org. Chem. 65 2000 3910 3919
2. M.R. Ali, K.H. Cheng, and J. Huang Assess the nature of cholesterol-lipid interactions through the chemical potential of cholesterol in phosphatidylcholine bilayers Proc. Natl. Acad. Sci. U.S.A. 104 2007 5372 5377 (Pubitemid 47175687)
3. R. Baker, and J. Hudec Long-range substituent effects in steroidal systems J. Chem. Soc. Chem. Commun. 1967 479 480
4. Y. Barenholz Sphingomyelin and cholesterol: From membrane biophysics and rafts to potential medical applications Subcell. Biochem. 37 2004 167 215
5. D.H.R. Barton The conformation of the steroid nucleus Experentia VI 1950 316 320
6. D.H.R. Barton The principles of conformational analysis Science 169 1970 539 544
7. F. Biasi, C. Mascia, M. Astegiano, E. Chiarpotto, M. Nano, B. Vizio, G. Leonarduzzi, and G. Poli Trojan horse-like behavior of a biologically representative mixture of oxysterols Free Radic. Biol. Med. 47 2009 1731 1741 (Pubitemid 38401939)
8. A. Carpinteiro, C. Dumitru, M. Schenck, and E. Gulbins Ceramide-induced cell death in malignant cells Cancer Lett. 264 2008 1 10
9. A.E. Cremesti, F.M. Goni, and R. Kolesnick Role of sphingomyelinase and ceramide in modulating rafts: Do biophysical properties determine biological outcome? FEBS Lett. 531 2002 47 53 (Pubitemid 35232783)
10. M. Edidin The state of lipid rafts: From model membranes to cells Annu. Rev. Biophys. Biomol. Struct. 32 2003 257 283 (Pubitemid 37056230)
11. R.M. Epand, D. Bach, N. Borochov, and E. Wachtel Cholesterol crystalline polymorphism and the solubility of cholesterol in phosphatidylserine Biophys. J. 78 2000 866 873 (Pubitemid 30211844)
12. A. Federico, and M.T. Dotti Cerebrotendinous xanthomatosis H.W. Moser, Handbook of Clinical Neurology Neurodystrophies and Neurolipidoses vol. 22 1996 Elsevier Science BV Amsterdam 599 613
13. S.A. Galema, J.B.F.N. Engberts, H. Hoiland, and G.M. Ferrland Informative thermodynamic properties of the effect of stereochemistry on carbohydrate hydration J. Phys. Chem. 97 1993 6885 6889
14. F.M. Goñi, and A. Alonso Effects of ceramide and other simple sphingolipids on membrane lateral structure Biochim. Biophys. Acta 1788 2009 169 177
15. T. Harder Formation of functional cell membrane domains: The interplay of lipid- and protein-mediated interactions Philos. Trans. R. Soc. Lond. B, Biol. Sci. 358 2003 863 868 (Pubitemid 36639709)
16. G.P. Holland, and T.M. Alam Unique backbone-water interaction detected in sphingomyelin bilayers with H-1/P-31 and H-1/C-13 HETCOR MAS-NMR spectroscopy Biophys. J. 95 2008 1189 1198
17. D. Huster, H.A. Scheidt, K. Arnold, A. Herrmann, and P. Müller Desmosterol may replace cholesterol in lipid membranes Biophys. J. 88 2005 1838 1844 (Pubitemid 40976197)
18. J.N. Israelachvili Intermolecular and Surface Forces 1992 Academic Press Ltd. San Diego, CA, USA
19. W.-L. Jeng, and B.-C. Han Coprostanol in a sediment core from the anoxic Tan-Shui estuary Taiwan Est. Coast. Shelf Sci. 42 1996 727 735 (Pubitemid 26287586)
20. C. Kubli-Garfias, R. Vázquez, A.J. Cooney, and F. Larrea Ab initio electronic structure of the progestogen norethisterone and its 5 alpha-derivatives J. Steroid Biochem. Mol. Biol. 82 2002 385 391 (Pubitemid 36187401)
21. E. Lancelot, and C. Grauby-Heywang Comparison of the interaction of dihydrocholesterol and cholesterol with sphingolipid or phospholipid Langmuir monolayers Colloid Surf. B 59 2007 81 86 (Pubitemid 47016927)
22. K.Y.C. Lee, J.F. Klingler, and H.M. McConnell Electric field-induced concentration gradients in lipid monolayers Science 263 1994 655 658
23. R.N.A.H. Lewis, D.A. Mannock, and R.N. McElhaney Differential scanning calorimetry in the study of lipid phase transitions in model and biological membranes: practical considerations A. Dopico, Methods in Membrane Lipids 2007 Humana Press Totown, NJ 171 195 (Pubitemid 350183689)
24. B. Maggio, G.A. Borioli, M. Del Boca, L. De Tullio, M.L. Fanani, R.G. Oliveira, C.M. Rosetti, and N. Wilke Composition-driven surface domain structuring mediated by sphingolipids and membrane-active proteins Cell Biochem. Biophys. 50 2008 79 109
25. D.A. Mannock, T.J. McIntosh, X. Jiang, D.F. Covey, and R.N. McElhaney Effects of natural and enantiomeric cholesterol on the thermotropic phase behavior and structure of egg sphingomyelin bilayers Biophys. J. 84 2003 1038 1046 (Pubitemid 36133428)
26. D.A. Mannock, R.N.A.H. Lewis, and R.N. McElhaney Comparative calorimetric and spectroscopic studies of the effects of lanosterol and cholesterol on the thermotropic phase behavior and organization of dipalmitoylphosphatidylcholine bilayer membranes Biophys. J. 91 2006 3327 3340
27. D.A. Mannock, M.Y. Lee, R.N. Lewis, and R.N. McElhaney Comparative calorimetric and spectroscopic studies of the effects of cholesterol and epicholesterol on the thermotropic phase behaviour of dipalmitoylphosphatidylcholine bilayer membranes Biochim. Biophys. Acta 1778 2008 2191 2202
28. D.A. Mannock, R.N.A.H. Lewis, and R.N. McElhaney A calorimetric and spectroscopic comparison of the effects on ergosterol and cholesterol on the thermotropic phase behavior of dipalmitoylphosphatidylcholine bilayer membranes Biochim. Biophys. Acta 1798 2010 376 388
29. D.A. Mannock, R.N.A.H. Lewis, T.P.W. McMullen, and R.N. McElhaney The effect of variations in phospholipid and sterol structure on the nature of lipid-sterol interactions in lipid bilayer model membranes Chem. Phys. Lipids 163 2010 403 448
30. T.P.W. McMullen, R.N.A.H. Lewis, and R.N. McElhaney Differential scanning calorimetric study of the effect of cholesterol on the thermotropic phase behavior of a homologous series of linear saturated phosphatidylcholines Biochemistry 32 1993 516 522
31. 31P NMR spectroscopic studies of the effects of cholesterol and androstenol on the thermotropic behavior and organization of phosphatidylcholine bilayers Biophys. J. 66 1994 741 752
32. T.P. McMullen, R.N.A.H. Lewis, and R.N. McElhaney Cholesterol- phospholipid interactions, the liquid-ordered phase and lipid rafts in model and biological membranes Curr. Opin. Colloid Interface Sci. 8 2004 459 468
33. T.P. McMullen, R.N.A.H. Lewis, and R.N. McElhaney Calorimetric and spectroscopic studies of the effects of cholesterol on the thermotropic phase behavior and organization of a homologous series of linear saturated phosphatidylglycerol bilayer membranes Biochim. Biophys. Acta 1788 2009 345 357
34. D.J. McNamara, A. Proia, and T.A. Miettinen Thin-layer and gas-liquid-chromatographic identification of neutral steroids in human and rat feces J. Lipid Res. 22 1981 474 484 (Pubitemid 11076141)
35. S. Munro Lipid rafts: elusive or illusive? Cell 115 2003 377 388 (Pubitemid 37456801)
36. I. Novak, and B. Kovac Electronic structure and biological activity of steroids Biophys. Chem. 78 1999 233 240 (Pubitemid 29189163)
37. T.K.M. Nyholm, M. Nylund, and J.P. Slotte A calorimetric study of binary mixtures of dihydrosphingomyelin and sterols, sphingomyelin, or phosphatidylcholine Biophys. J. 84 2003 3138 3146 (Pubitemid 36531761)
38. B. Ramstedt, and J.P. Slotte Sphingolipids and the formation of sterol-enriched ordered membrane domains Biochim. Biophys. Acta 1758 2006 1945 1956 (Pubitemid 44879357)
39. 2H NMR, FTIR, DSC and neutron scattering study Biophys. J. 61 1992 1025 1035
40. T. Rog, M. Pasenkiewicz-Gierula, I. Vattulainen, and M. Karttunen Ordering effects of cholesterol and its analogues Biochim. Biophys. Acta 1788 2009 97 121
41. C.M. Rosetti, B. Maggio, and N. Wilke Micron-scale phase segregation in lipid monolayers induced by myelin basic protein in the presence of a cholesterol analog Biochim. Biophys. Acta 1798 2010 498 505
42. J.K. Rugutt, and K.J. Rugutt Relationships between molecular properties and antimycobacterial activities of steroids Nat. Prod. Lett. 16 2002 107 113
43. B.L. Stottrup, and S.L. Keller Phase behaviour of lipid monolayers containing DPPC and cholesterol analogs Biophys. J. 90 2006 3176 3183
44. O. Takahashi, K. Yamasaki, Y. Kohno, K. Ueda, H. Suezawa, and M. Nishio The conformation of levopimaric acid investigated by high-level ab initio MO calculations. Possibility of the CH/π hydrogen bond Tetrahedron 65 2009 3525 3528
45. S. Vainio, M. Jansen, M. Koivusalo, T. Róg, M. Karttunen, I. Vattulainen, and E. Ikonen Significance of sterol structural specificity. Desmosterol cannot replace cholesterol in lipid rafts J. Biol. Chem. 281 2006 348 355 (Pubitemid 43671195)