Thiosquaramides: pH switchable anion transporters.

ABSTRACT: The transport of anions across cellular membranes is an important biological function governed by specialised proteins. In recent years, many small molecules have emerged that mimick the anion transport behaviour of these proteins, but only a few of these synthetic molecules also display the gating/switching behaviour seen in biological systems. A small series of thiosquaramides was synthesised and their pH-dependent chloride binding and anion transport behaviour was investigated using ¹H NMR titrations, single crystal X-ray diffraction and a variety of vesicle-based techniques. Spectrophotometric titrations and DFT calculations revealed that the thiosquaramides are significantly more acidic than their oxosquaramide analogues, with pK_a values between 4.0 and 9.

SUBMITTER: Busschaert N 

PROVIDER: S-EPMC4486358 | biostudies-literature | 2014 Sep

REPOSITORIES: biostudies-literature