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

被引:10
作者
Bach, D. [1 ]
Epand, R. F. [2 ]
Epand, R. M. [2 ]
Miller, I. R. [1 ]
Wachtel, E. [3 ]
机构
[1] Weizmann Inst Sci, Dept Biol Chem, IL-76110 Rehovot, Israel
[2] McMaster Univ, Dept Biochem & Biomed Sci, Hamilton, ON L8N 3Z5, Canada
[3] Weizmann Inst Sci, Chem Res Infrastruct Unit, IL-76110 Rehovot, Israel
基金
加拿大自然科学与工程研究理事会;
关键词
Oxidized cholesterol; Phospholipids; Schiff base; X-ray diffraction; Differential scanning calorimetry; SCHIFF-BASE FORMATION; OZONATION PRODUCT; OZONE FORMATION; PHASE-BEHAVIOR; OZONOLYSIS; MODULATION; PHOSPHATIDYLETHANOLAMINE; OXYSTEROLS; APOPTOSIS; RESIDE;
D O I
10.1016/j.chemphyslip.2009.07.006
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The effect of an oxidized form of cholesterol, 3 beta-hydroxy-5-oxo-5,6-secocholestan-6-al on the thermotropic and structural properties of phospholipid membranes was investigated by differential scanning calorimetry and X-ray diffraction and compared with that of cholesterol. The phospholipids studied included 1palmitoyl-2-oleoylphosphatidylserine, dipalmitoleoylphosphatidylethanolamine, 1-palmitoyl-2-oleoylphosphatidylethanolamine, dipalmitoleoylphosphatidylcholine, 1-palmitoyl-2-oleoylphosphatidylcholine. Depending on the constituent phospholipids, the oxidized cholesterol is observed to shift phase transitions, disrupt stacking, modify interbilayer spacings and promote increased negative membrane curvature. We determined by absorption spectroscopy that the amino group of phosphatidylserine forms a Schiff base with the aldehyde group of the 3 beta-hydroxy-5oxo-5,6-secocholestan-6-al as was previously found for the amino group of phosphatidylethanolamine. This result strengthens the biologically significant finding that not only amino groups of proteins but also amino groups of phospholipids are able to form a Schiff base with oxidized cholesterol. The marked triangular shape of the Schiff base complex with phosphatidylethanolamine may explain how 3 beta-hydroxy-5-oxo-5,6-secocholestan-6-al can promote increased negative curvature in the hexagonal phase, as compared to cholesterol, even though its increased polarity would favor a location closer to the interface with water. (C) 2009 Elsevier Ireland Ltd. All rights reserved.
引用
收藏
页码:95 / 102
页数:8
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