Abstract
A series of symmetrical and unsymmetrical alkyl tren based tris-thiourea anion transporters were synthesised and their anion binding and transport properties studied. Overall, increasing the steric bulk of the substituents resulted in improved chloride binding and transport abilities. Including a macrocycle in the scaffold enhanced the selectivity of chloride transport in the presence of fatty acids, by reducing the undesired H+ flux facilitated by fatty acid flip-flop. This study demonstrates the benefit of including enforced steric hindrance and encapsulation in the design of more selective anion receptors.
Highlights
Anion transporters that can restore chloride flux through apical epithelial cell membranes have potential to function as ‘channel replacement therapies’ to ameliorate the symptoms of diseases, such as cystic fibrosis (CF) [1,2,3,4,5,6,7]
The rate determining step in the transport cycle is diffusion of the free receptor, while fatty acid flip-flop provides an alternate pathway through the membrane for anion transporters, which results in an increased rate of H+ /Cl− symport
We have shown that increasing the steric hindrance of simple tren based receptors results in anWe increase in binding affinity towards chloride
Summary
Anion transporters that can restore chloride flux through apical epithelial cell membranes have potential to function as ‘channel replacement therapies’ to ameliorate the symptoms of diseases, such as cystic fibrosis (CF) [1,2,3,4,5,6,7]. The rate determining step in the transport cycle is diffusion of the free receptor, while fatty acid flip-flop provides an alternate pathway through the membrane for anion transporters, which results in an increased rate of H+ /Cl− symport. +/OH− or transport or fatty fatty acid calixpyrroles thatthat increasing the the degree of encapsulation of a receptor resultsresults in a high of chloride selectivity, increasing degree of encapsulation of a receptor in adegree high degree of chloride which is not compromised in the presence of fatty acids [19]. To further investigate this phenomenon, selectivity, which is not compromised in the presence of fatty acids [19]. As investigations into the Cl− > H+/OH− transport selectivity were performed
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