Imidazole derivatives as artificial water channel building-blocks: structural design influence on water permeability,Faraday Discussions

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Imidazole derivatives as artificial water channel building-blocks: structural design influence on water permeability
Faraday Discussions ( IF 3.3 ) Pub Date : 2018-07-31 , DOI: 10.1039/c8fd00024g
Zhanhu Sun _{1,

2,

3,

4,

5} , Istvan Kocsis _{1,

2,

3,

4,

5} , Yuhao Li _{1,

2,

3,

4,

5} , Yves-Marie Legrand _{1,

2,

3,

4,

5} , Mihail Barboiu _{1,

2,

3,

4,

5}

Affiliation

A series of mono- and di-ureidoethylimidazole derivatives were tested as self-assembled supramolecular channels for water transport. Several structural behaviours were compared in order to gain insight on the structure–water transport activity relationship. The three main features that are critical to tailor artificial water channel building blocks are: (i) the selectivity of the hydrophilic head, (ii) the H-bonding scaffold favouring the directional self-assembly, and (iii) the lipophilic tail for the compatibility with the hydrophobic environment of the lipid bilayer. The designed compounds bear one or two imidazole heads, one or two urea moieties, and different lipophilic tails. Water transport experiments were performed in order to assess the critical parameters. For that, large unilamellar vesicles (LUV) were fabricated using a mixture of phosphatidylcholine, phosphatidylserine and cholesterol. The bilayer of the LUV constituted a membrane between an intra and an extra vesicular medium. The artificial water channel candidates are put in the presence of this membrane to improve its water permeability. The permeation of elements other than water is ideally maintained to a minimum in order to achieve selective water filtration. In this study the effect of additional urea moieties, as well as its absence, was evidenced as detrimental for the permeation and the influence of the tail was also investigated.

中文翻译：

咪唑衍生物作为人造水通道的组成部分：结构设计对透水性的影响

测试了一系列单-和二-脲基乙基咪唑衍生物作为自组装的超分子水通道。比较了几种结构行为，以便深入了解结构与水的运输活动之间的关系。定制人造水通道构件的三个主要特征是：（i）亲水头的选择性，（ii）有利于定向自组装的H键合支架，以及（iii）亲水性头对于与脂质双层疏水环境的相容性。设计的化合物带有一个或两个咪唑头，一个或两个尿素部分以及不同的亲脂性尾巴。进行水运输实验以评估关键参数。为了那个原因，使用磷脂酰胆碱，磷脂酰丝氨酸和胆固醇的混合物制备大的单层囊泡（LUV）。LUV的双层构成内部和外部囊泡介质之间的膜。将人造水通道候选物置于该膜的存在下以改善其水渗透性。为了实现选择性的水过滤，理想地将除水以外的其他元素的渗透保持在最低水平。在这项研究中，另外的尿素部分的影响以及它的不存在被证明对渗透是有害的，并且还研究了尾巴的影响。将人造水通道候选物置于该膜的存在下以改善其水渗透性。为了实现选择性的水过滤，理想地将除水以外的其他元素的渗透保持在最低水平。在这项研究中，另外的尿素部分的影响以及它的不存在被证明对渗透是有害的，并且还研究了尾巴的影响。将人造水通道候选物置于该膜的存在下以改善其水渗透性。为了实现选择性的水过滤，理想地将除水以外的其他元素的渗透保持在最低水平。在这项研究中，另外的尿素部分的影响以及它的不存在被证明对渗透是有害的，并且还研究了尾巴的影响。

更新日期：2018-09-28

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