THE EFFECT OF THE STEROL OXYGEN FUNCTION ON THE INTERACTION WITH PHOSPHOLIPIDS

被引:24
作者
DEMEL, RA [1 ]
LALA, AK [1 ]
KUMARI, SN [1 ]
VANDEENEN, LLM [1 ]
机构
[1] INDIAN INST TECHNOL, DEPT CHEM, BIOORGAN LAB, BOMBAY 400076, INDIA
关键词
D O I
10.1016/0005-2736(84)90526-1
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 cholesteryl ethers (namely cholesteryl methyl ether, cholesteryl ethyl ether, cholesteryl n-propyl ether, cholesteryl isopropyl ether, cholesteryl butyl ether, cholesteryl methoxymethyl ether, cholesteryl (2''-hydroxy)-3-ethyl ether) and cholesteryl ester (namely cholesteryl acetate) is tested on the interaction with phosphatidylcholines in liquid-crystalline and crystalline state. The interfacial properties of sterols are tested at the air-water interface. The cholesteryl ethers show a reduced interfacial stability with increasing hydrophobicity of the ether-linked moiety. The interaction between the sterol derivatives and phospholipids in mixed monolayers is indicated by measuring the deviation from the simple addivity rule (condensing effect). An interaction is found only for cholesteryl (2''-hydroxy)-3-ethyl ether, cholesteryl methyl ether and cholesteryl ethyl ether. These sterols also reduce the glucose permeability of liposomal membranes in this order. In this respect cholesteryl (2''-hydroxy)-3-ethyl ether is as effective as cholesterol. Cholesteryl methyl ether and cholesteryl ethyl ether show 62% and 33% of the effect observed with cholesterol. The effect of the sterol derivatives on the gel-to-liquid-crystalline phase transition of dipalmitoylphosphatidylcholine is measured by differential scanning calorimetry. Cholesteryl methyl ether, cholesteryl ethyl ether and cholesteryl (2''-hydroxy)-3-ethyl ether reduce the energy content of the phase transition nearly as effectively as cholesterol, cholesteryl n-propyl ether has only a small effect. Although cholesteryl acetate and cholesteryl methoxymethyl ether have no condensing or permeability-reducing effect, they have a considerable effect on the gel-to-liquid-crystalline phase transition. Cholesteryl isopropyl ether and cholesteryl butyl ether have no effect. A free 3.beta.-hydroxy group is not a prerequisite to observe a sterol-like effect in membranes. However, the interfacial stability and the orientation of the sterol and oxygen moiety at the sterol 3-position are important.
引用
收藏
页码:142 / 150
页数:9
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