Submerging a Biomimetic Metallo‐Receptor in Water for Molecular Recognition: Micellar Incorporation or Water Solubilization? A Case Study,Chemistry - A European Journal

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Submerging a Biomimetic Metallo‐Receptor in Water for Molecular Recognition: Micellar Incorporation or Water Solubilization? A Case Study
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2018-11-26 , DOI: 10.1002/chem.201804768
Solène Collin ₁ , Arnaud Parrot ₁ , Lionel Marcelis ₂ , Emilio Brunetti _{2,

3} , Ivan Jabin ₃ , Gilles Bruylants ₂ , Kristin Bartik ₂ , Olivia Reinaud ₁

Affiliation

Molecular recognition in water is an important topic, but a challenging task due to the very competitive nature of the medium. The focus of this study is the comparison of two different strategies for the water solubilization of a biomimetic metallo‐receptor based on a poly(imidazole) resorcinarene core. The first relies on a new synthetic path for the introduction of hydrophilic substituents on the receptor, at a remote distance from the coordination site. The second involves the incorporation of the organosoluble metallo‐receptor into dodecylphosphocholine (DPC) micelles, which mimic the proteic surrounding of the active site of metallo‐enzymes. The resorcinarene ligand can be transferred into water through both strategies, in which it binds Zn^II over a wide pH window. Quite surprisingly, very similar metal ion affinities, pH responses, and recognition properties were observed with both strategies. The systems behave as remarkable receptors for small organic anions in water at near‐physiological pH. These results show that, provided the biomimetic site is well structured and presents a recognition pocket, the micellar environment has very little impact on either metal ion binding or guest hosting. Hence, micellar incorporation represents an easy alternative to difficult synthetic work, even for the binding of charged species (metal cations or anions), which opens new perspectives for molecular recognition in water, whether for sensing, transport, or catalysis.

中文翻译：

将仿生金属受体浸入水中进行分子识别：胶束掺入或水增溶？案例研究

水中的分子识别是一个重要的话题，但由于该介质的竞争性很强，因此具有挑战性。这项研究的重点是比较两种基于聚咪唑间苯二甲烯核心的仿生金属受体水溶解的不同策略。第一种方法是依靠新的合成途径将亲水性取代基引入受体，且距离配位点较远。第二个过程涉及将有机可溶性金属受体掺入十二烷基磷酸胆碱（DPC）胶束中，该胶束模仿金属酶活性位点的蛋白质周围。间苯二烯配体可以通过两种策略转移到水中，在该策略中，它与Zn ^II结合在较宽的pH范围内。出乎意料的是，两种策略都观察到非常相似的金属离子亲和力，pH响应和识别特性。该系统在接近生理pH值的情况下，可作为水中小型有机阴离子的出色受体。这些结果表明，只要仿生位点结构良好并具有识别袋，胶束环境对金属离子结合或客体宿主的影响就很小。因此，胶束掺入代表了困难的合成工作的简便替代方案，即使对于带电物质（金属阳离子或阴离子）的结合也是如此，这为在水中进行分子识别（无论是传感，运输还是催化）开辟了新的前景。

更新日期：2018-11-26

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