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通过表面压力测量和布鲁斯特角显微镜研究糖生物碱番茄碱与二肉豆蔻酰磷脂酰胆碱(DMPC)和甾醇单层的相互作用。

Interaction of the glycoalkaloid tomatine with DMPC and sterol monolayers studied by surface pressure measurements and Brewster angle microscopy.

作者信息

Stine Keith J, Hercules Rachel K, Duff Joy D, Walker Barry W

机构信息

Department of Chemistry and Biochemistry, Center for Molecular Electronics, University of Missouri- St. Louis, Saint Louis, Missouri 63121, USA.

出版信息

J Phys Chem B. 2006 Nov 9;110(44):22220-9. doi: 10.1021/jp056139j.

Abstract

The interaction of the glycoalkaloid tomatine with monolayers of dimyristoylphosphatidylcholine (DMPC) and cholesterol, as well as other selected sterols, has been investigated using surface pressure measurements at constant area and Brewster angle microscopy (BAM). The interaction of tomatine with sterol monolayers is found to vary with the structure of the sterol. The interaction of tomatine with cholesterol-containing monolayers results in a surface pressure increase accompanied by the appearance of a mottled texture. Morphological changes are observed that suggest the formation of tomatine-cholesterol complexes that aggregate at the water-air interface. No morphology change observable by BAM is observed for monolayers containing epicholesterol, suggesting that the stereochemistry of hydrogen bonding between the sterol and the sugar units on tomatine is of particular significance. Strong interactions are observed with cholestanol- and coprostanol-containing monolayers, and BAM reveals formation of spiked aggregates upon interaction with 7:3 mole ratio DMPC/coprostanol mixed monolayers. More modest surface pressure changes are observed for cholestenone- and epicoprostanol-containing monolayers. A much smaller surface pressure increase is observed when tomatine is injected beneath a pure DMPC monolayer.

摘要

已使用恒定面积下的表面压力测量和布鲁斯特角显微镜(BAM)研究了糖生物碱番茄碱与二肉豆蔻酰磷脂酰胆碱(DMPC)和胆固醇单层以及其他选定固醇的相互作用。发现番茄碱与固醇单层的相互作用随固醇结构而变化。番茄碱与含胆固醇单层的相互作用导致表面压力增加,并伴有斑驳纹理的出现。观察到形态变化,表明形成了在水-空气界面聚集的番茄碱-胆固醇复合物。对于含表胆固醇的单层,未观察到BAM可检测到的形态变化,这表明固醇与番茄碱上糖单元之间氢键的立体化学具有特别重要的意义。观察到与含胆甾烷醇和粪甾烷醇的单层有强烈相互作用,并且BAM显示与7:3摩尔比的DMPC/粪甾烷醇混合单层相互作用时形成了尖刺状聚集体。对于含胆甾烯酮和表粪甾烷醇的单层,观察到的表面压力变化较小。当将番茄碱注入纯DMPC单层下方时,观察到的表面压力增加要小得多。

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