A product of ozonolysis of cholesterol alters the biophysical properties of phosphatidylethanolamine membranes.
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.
Wachtel
Ellen
E
Chemical Research Infrastructure Unit, Weizmann Institute of Science, Rehovot, Israel.
Bach
Diana
D
Epand
Raquel F
RF
Tishbee
Arye
A
Epand
Richard M
RM
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
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