The oxidized form of cholesterol 3β-hydroxy-5-oxo-5,6-secocholestan-6-al induces structural and thermotropic changes in phospholipid membranes

Chemistry and Physics of Lipids

Volumn 161, Issue 2, 2009, Pages 95-102

  Bach, D ^a   Epand, R F ^b   Epand, R M ^b   Miller, I R ^a   Wachtel, E ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

^b MCMASTER UNIVERSITY   (Canada)

Author keywords

Differential scanning calorimetry; Oxidized cholesterol; Phospholipids; Schiff base; X ray diffraction

Indexed keywords

1 PALMITOYL 2 OLEOYLPHOSPHATIDYLSERINE; 2 OLEOYL 1 PALMITOYLPHOSPHATIDYLCHOLINE; ALDEHYDE; CHOLESTEROL; CHOLESTEROL 3BETA HYDROXY 5 OXO 5,6 SECOCHOLESTAN 6 AL; DIPALMITOLEOYLPHOSPHATIDYLCHOLINE; PHOSPHATIDYLETHANOLAMINE; PHOSPHATIDYLSERINE; PHOSPHOLIPID; PROTEIN; SCHIFF BASE; UNCLASSIFIED DRUG; WATER;

ABSORPTION SPECTROSCOPY; ARTICLE; CONTROLLED STUDY; DIFFERENTIAL SCANNING CALORIMETRY; EXPERIMENTAL MODEL; OXIDATION; PHASE TRANSITION; PHOSPHOLIPID BILAYER; PHOSPHOLIPID MEMBRANE; PRIORITY JOURNAL; PROTEIN STRUCTURE; X RAY DIFFRACTION;

CALORIMETRY, DIFFERENTIAL SCANNING; LIPID BILAYERS; MEMBRANES; PHOSPHATIDYLCHOLINES; PHOSPHOLIPIDS; TEMPERATURE; THERMODYNAMICS; WATER; X-RAY DIFFRACTION;

EID: 69849098845     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2009.07.006     Document Type: Article

References (29)

1. Bach D., Wachtel E., Borochov N., Senisterra G., and Epand R.M. Phase behavior of heteroacid phosphatidylserines and cholesterol. Chem. Phys. Lipids 63 (1992) 105-113
2. Bach D., Borochov N., and Wachtel E. Phase separation of cholesterol and the interaction of ethanol with phosphatidylserine-cholesterol bilayer membranes. Chem. Phys. Lipids 114 (2002) 123-130
3. Bach D., Epand R.F., Epand R.M., and Wachtel E. Interaction of 7-ketocholesterol with two major components of the inner leaflet of the plasma membrane: phosphatidylethanolamine and phosphatidylserine. Biochemistry 47 (2008) 3004-3012
4. Bach D., Wachtel E., and Miller I.R. Kinetics of Schiff base formation between the cholesterol ozonolysis product 3-β-hydroxy-5-oxo-6,6-secocholestan-6-al and phosphatidylethanolamine. Chem. Phys. Lipids 157 (2009) 51-55
5. Biesche J., Zhang Q., Powers E.T., Lerner R.A., and Kelly J.W. Oxidative metabolites accelerate Alzheimers amyloidogenesis by a two-step mechanism, eliminating the requirement for nucleation. Biochemistry 44 (2005) 4977-4983
6. Epand R.M., Hughes D.W., Sayer B.G., Borochov N., Bach D., and Wachtel E. Novel properties of cholesterol-dioleoylphosphatidylcholine mixtures. Biochim. Biophys. Acta 1616 (2003) 196-208
7. Epand R.M., Epand R.F., Hughes D.W., Sayer B.G., Borochov N., Bach D., and Wachtel E. Phosphatidylcholine structure determines cholesterol solubility and lipid polymorphism. Chem. Phys. Lipids 135 (2005) 39-53
8. Evans D.F., and Wennerstrom H. The Colloidal Domain (1994), VCH Publishers, Inc., New York pp. 12-16
9. Greenwood A.I., Pan J., Mills T.T., Nagle J.F., Epand R.M., and Tristram-Nagle S. CRAC motif peptide of the HIV-1 gp41 protein thins SOPC membranes and interacts with cholesterol. Biochim. Biophys. Acta 1778 (2008) 1120-1130
10. Harroun T.A., Katsaras J., and Wassall S.R. Cholesterol hydroxyl group is found to reside in the center of a polyunsaturated lipid membrane. Biochemistry 45 (2006) 1227-1233
11. Harroun T.A., Katsaras J., and Wassall S.R. Cholesterol is found to reside in the center of a polyansaturated lipid membrane. Biochemistry 47 (2008) 7090-7096
12. Hauser H. Some aspects of the phase behaviour of charged lipids. Biochim. Biophys. Acta 772 (1984) 37-50
13. Hodzic A., Rappolt M., Amenitsch H., Laggner P., and Pabst G. Differential modulation of membrane structure and fluctuations by plant sterols and cholesterol. Biophys. J. 94 (2008) 3935-3944
14. Petrache H.I., Harries D., and Parsegian V.A. Alteration of lipid membrane rigidity by cholesterol and its metabolic precursors. Macromol. Symp. 219 (2005) 39-50
15. Privalov G., Kavina V., Freire E., Privalov P.L., et al. Precise scanning calorimeter for studying thermal properties of biological macromolecules in dilute solution. Anal. Biochem. 232 (1995) 79-85
16. Pryor W.A., Wang K., and Bermudez E. Cholesterol ozonation products as biomarkers for ozone exposure in rats. Biochem. Biophys. Res. Commun. 188 (1992) 618-623
17. Pulfer M.K., and Murphy R.C. Formation of biologically active oxysterols during ozonolysis of cholesterol present in lung surfactant. J. Biol. Chem. 279 (2004) 26331-26338
18. Salva A., Donoso J., Frau J., and Munoz F. Theoretical studies on Schiff base formation of vitamin B6 analogues. J. Mol. Struct. 577 (2002) 229-238
19. 2H nuclear magnetic resonance study. Biochemistry 29 (1990) 10676-10684
20. Sathishkumar K., Haque M., Perumal T.E., Francis J., and Uppu R.M. A major ozonation product of cholesterol, 3β-hydroxy-5-oxo-5,6-secocholestan-6-al, induces apoptosis in H9c2 cardiomyoblasts. FEBS Lett. 579 (2005) 6444-6450
21. Sathishkumar K., Xi X., Martin R., and Uppu R.M. Cholesterol secoaldehyde, an ozonation product of cholesterol, induces amyloid aggregation and apoptosis in murine GT1-7 hypothalamic neurons. J. Alzheimers Dis. 11 (2007) 261-274
22. Sathishkumar K., Murthy S.N., and Uppu R.M. Cytotoxic effects of oxysterols produced during ozonolysis of cholesterol in murine GT1-7 hypothalamic neurons. Free Radic. Res. 41 (2007) 82-88
23. Scott H.L., and Kalaskar S. Lipid chains in model membranes: a Monte Carlo study. Biochemistry 28 (1989) 3567-3591
24. Takeuchi C., Galve R., Wittner D.P., Wentworth A.D., Troseth R.P., Lerner R.A., and Wentworth Jr. P. Proatherogenic effects of the cholesterol ozonolysis products, atheronal A and atheronal B. Biochemistry 45 (2006) 7162-7170
25. Villalain J. Location of cholesterol in model membranes by magic-angle-sample-spinning NMR. Eur. J. Biochem. 241 (1996) 586-593
26. Wachtel E., Bach D., Epand R.F., Tishbee A., and Epand R.M. A product of ozonolysis of cholesterol alters the biophysical properties of phosphatidylethanolamine membranes. Biochemistry 45 (2006) 1345-1351
27. Wentworth Jr. P., McDunn J.E., Wentworth A.D., Takeuchi C., Nieva J., Jones T., Bautista C., Ruedi J.M., Gutierrez A., Janda K.D., Babior B.M., Eschenmoser A., and Lerner R.A. Evidence for antibody-catalyzed ozone formation in bacterial killing and inflammation. Science 298 (2002) 2195-2199
28. Wentworth Jr. P., Nieva J., Takeuchi C., Galve R., Wentworth A.D., Dilley R.B., DeLaria G.A., Saven A., Babior B.M., Janda K.D., Eschenmoser A., and Lerner R.A. Evidence for ozone formation in human atherosclerotic arteries. Science 302 (2003) 1053-1056
29. Yeagle P.L. Modulation of membrane function by cholesterol. Biochimie 73 (1991) 1303-1310