Fructose controlled ionophoric activity of a cholate-boronic acid.

Fructose controlled ionophoric activity of a cholate-boronic acid.
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果糖控制胆酸硼酸的离子载体活性。

DOI:
10.1039/c4ob00165f
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发表时间:
2014
影响因子:
3.2
通讯作者:
Brown JR
Brown JR
中科院分区:
化学3区
文献类型:
--
作者:
Brown JR

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Wulff型硼酸已被证明在pH 8.2下通过将Na+转运通过磷脂双层而充当离子载体。合成了胆酸盐-硼酸缀合物,并显示其是离子载体,尽管胆酸盐部分的羟基内衬面没有增强离子转运。机制研究表明,载体机制的Na+运输。果糖(>5 mM)的加入强烈抑制胆酸盐-硼酸缀合物的离子载体活性,这反映在该化合物分配到有机相中的能力的强烈降低。使用在pH 8.2下测量的果糖/硼酸结合常数对分区和离子传输数据进行建模,显示出与果糖/硼酸络合程度的良好相关性,并建议高极性果糖/硼酸络合物是差的离子载体。离子转运对果糖的敏感性意味着在周围环境中具有由多糖调节的活性的基于硼酸的抗生素离子载体可能是可访问的。
Wulff-type boronic acids have been shown to act as ionophores at pH 8.2 by transporting Na+ through phospholipid bilayers. A cholate–boronic acid conjugate was synthesised and shown to be an ionophore, although the hydroxyl-lined face of the cholate moiety did not enhance ion transport. Mechanistic studies suggested a carrier mechanism for Na+ transport. The addition of fructose (>5 mM) strongly inhibited ionophoric activity of the cholate–boronic acid conjugate, mirrored by a strong decrease in the ability of this compound to partition into an organic phase. Modelling of the partitioning and ion transport data, using a fructose/boronic acid binding constant measured at pH 8.2, showed a good correlation with the extent of fructose/boronic acid complexation and suggested high polarity fructose/boronic acid complexes are poor ionophores. The sensitivity of ion transport to fructose implies that boronic acid-based antibiotic ionophores with activity modulated by polysaccharides in the surrounding environment may be accessible.
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