Differences in Interactions of Benzoic Acid and Benzoate with Interfaces.
Differences in Interactions of Benzoic Acid and Benzoate with Interfaces.
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DOI：
10.1021/acs.langmuir.6b02073
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发表时间：
2016-09-20
期刊：
影响因子：
--
通讯作者：
Crans DC
中科院分区：
文献类型：
--
作者：
Peters BJ;Groninger AS;Fontes FL;Crick DC;Crans DC
苯甲酸和苯甲酸酯与模型膜系统的相互作用，其特征在于了解的分子相互作用的两种形式的一个简单的芳香族酸与膜的组件。基于双（2乙基己基）磺基琥珀酸酯（AOT）的微乳液体系允许使用1D NMR和2D NMR光谱方法测定分子定位。发现苯甲酸和苯甲酸盐都渗透膜/水界面;然而，苯甲酸能够渗透得更深，因此更容易穿过膜。使用二棕榈酰磷脂酰胆碱的Langmuir单层模型系统用作细胞的通用膜脂质。单层的压缩等温线证明了与脂质单层的pH依赖性相互作用，并证实了反胶束模型系统中所示的pH依赖性观察结果。这些研究为苯甲酸盐无活性时苯甲酸的抗微生物活性提供了解释。此外，这些研究形成了我们正在研究吡嗪酸的细菌摄取模式的框架，吡嗪酸是吡嗪酰胺的活性形式，吡嗪酰胺是用于对抗结核病的一线药物。
The interaction of benzoic acid and benzoate with model membrane systems was characterized to understand the molecular interactions of the two forms of a simple aromatic acid with the components of the membrane. The microemulsion system based on bis(2ethylhexyl)sulfosuccinate (AOT) allowed determination of the molecular positioning using 1D NMR and 2D NMR spectroscopic methods. Benzoic acid and benzoate were both found to penetrate the membrane/water interfaces; however, the benzoic acid was able to penetrate much deeper and thus is more readily able to traverse a membrane. The Langmuir monolayer model system, using dipalmitoylphosphatidylcholine, was used as a generic membrane lipid for a cell. Compression isotherms of monolayers demonstrated a pH dependent interaction with a lipid monolayer and confirming the pH dependent observations shown in the reverse micellar model system. These studies provide an explanation for the antimicrobial activity of benzoic acid while benzoate is inactive. Furthermore, these studies form the framework upon which we are investigating the mode of bacterial uptake of pyrazinoic acid, the active form of pyrazinamide, a front line drug used to combat tuberculosis.
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