title: A product of ozonolysis of cholesterol alters the biophysical properties of phosphatidylethanolamine membranes.
abstract: There is evidence that some products of the reaction of ozone with cholesterol contribute to atherosclerosis. One of these compounds is 3beta-hydroxy-5-oxo-5,6-secocholestan-6-al. We have synthesized this compound and have demonstrated that it reacts with phosphatidylethanolamine to form a Schiff base. The 3beta-hydroxy-5-oxo-5,6-secocholestan-6-al also affects the physical properties of phosphatidylethanolamines. We show by both DSC and X-ray diffraction that it increases the negative curvature of the membrane. In addition, 3beta-hydroxy-5-oxo-5,6-secocholestan-6-al causes the lamellar phase to become disorganized, resulting in the loss of lamellar periodicity. The chemical and physical interactions of 3beta-hydroxy-5-oxo-5,6-secocholestan-6-al with phosphatidylethanolamines may contribute to damaging effects of this lipid on cell membranes, resulting in pathology.
authors.affiliation: Chemical Research Infrastructure Unit, Weizmann Institute of Science, Rehovot, Israel.
authors.forename: Ellen
authors.initials: E
authors.lastname: Wachtel
authors.forename: Diana
authors.initials: D
authors.lastname: Bach
authors.forename: Raquel F
authors.initials: RF
authors.lastname: Epand
authors.forename: Arye
authors.initials: A
authors.lastname: Tishbee
authors.forename: Richard M
authors.initials: RM
authors.lastname: Epand
mesh_terms: D002152:Calorimetry, Differential Scanning / Q000379:methods; D002776:Cholestanes / Q000737:chemistry / Q000378:metabolism; D002778:Cholestanones / Q000737:chemistry / Q000378:metabolism; D002784:Cholesterol / Q000737:chemistry / Q000378:metabolism*; D013058:Mass Spectrometry / Q000379:methods; D008566:Membranes / Q000737:chemistry* / Q000378:metabolism; D010126:Ozone / Q000378:metabolism*; D010714:Phosphatidylethanolamines / Q000737:chemistry* / Q000378:metabolism; D012545:Schiff Bases / Q000737:chemistry; D012632:Secosteroids / Q000737:chemistry / Q000378:metabolism; D013261:Sterols / Q000737:chemistry / Q000378:metabolism; D013696:Temperature; D014961:X-Ray Diffraction / Q000379:methods
chemical_list: C479527:5,6-secosterol; D002776:Cholestanes; D002778:Cholestanones; D010714:Phosphatidylethanolamines; D012545:Schiff Bases; D012632:Secosteroids; D013261:Sterols; C483858:phosphatidylethanolamine; D010126:Ozone; C082684:3-hydroxy-5-oxo-5,6-secocholestan-6-al; D002784:Cholesterol