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Calixarenes with halogen bond donors for anion transport

par Singh, Anurag ;Torres Huerta, Aaron ;Valkenier, Hennie ;Jabin, Ivan ;Martinez Crespo, Luis ;Renier, Nathan ;Vanderlinden, Tom;Tumanov, Nikolay;Wouters, Johan
Référence 1st Women in Supramolecular Chemistry (WISC) workshop (6th - 8th September 2021)
Publication Non publié, 2021-09-04

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Résumé :

Cystic fibrosis is a life-threatening disease caused by the mutation in Cystic Fibrosis Transmembrane Conductance Regulator (CFTR) protein, affecting chloride transport across cell membranes. One of the potential solutions is to utilize synthetic anion transporters (anionophores) for restoring the chloride transport process. The vast majority of reported synthetic chloride transporters use hydrogen bonds (HB) as an interaction between chloride and the anionophore. Halogen bonds (XBs) are another non-covalent interaction that are relatively less explored. These XBs can have comparable strength to HBs, but XB donors do not have acidic H-atoms, as they interact with anions using halogen atoms. This makes XB-based anionophores potentially less toxic than anionophores relying on HBs, as they are less likely to dissipate pH gradients.In our work, we employed halogen bond (XB) donating groups on a calix[6]arene backbone to obtain anion receptors. A series of calixarene-based molecules were designed and synthesized to screen them for binding and anion transport. Crystallization and NMR titration experiments were performed to explore anion binding with the receptors. After initial screening of the synthesized molecules for anion binding and transport, we further investigated the transport processes and mechanisms involved. XB and HB-based anionophores were compared and one of the XB-based compounds was found to selectively transport chloride over protons.