Photomodulation of Transmembrane Transport and Potential by Stiff-Stilbene Based Bis(thio)ureas.

Sander J Wezenberg, Li-Jun Chen, Jasper E Bos, Ben L Feringa, Ethan N W Howe, Xin Wu, Maxime A Siegler, Philip A Gale

Journal of the American Chemical Society 2022 Jan 12

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Membrane transport proteins fulfill important regulatory functions in biology with a common trait being their ability to respond to stimuli in the environment. Various small-molecule receptors, capable of mediating transmembrane transport, have been successfully developed. However, to confer stimuli-responsiveness on them poses a fundamental challenge. Here we demonstrate photocontrol of transmembrane transport and electric potential using bis(thio)ureas derived from stiff-stilbene. UV-vis and 1H NMR spectroscopy are used to monitor E-Z photoisomerization of these bis(thio)ureas and 1H NMR titrations reveal stronger binding of chloride to the (Z)-form than to the (E)-form. Additional insight into the binding properties is provided by single crystal X-ray crystallographic analysis and DFT geometry optimization. Importantly, the (Z)-isomers are much more active in transmembrane transport than the respective (E)-isomers as shown through various assays. As a result, both membrane transport and depolarization can be modulated upon irradiation, opening up new prospects toward light-based therapeutics as well as physiological and optopharmacological tools for studying anion transport-associated diseases and to stimulate neuronal activity, respectively.

Citation

Sander J Wezenberg, Li-Jun Chen, Jasper E Bos, Ben L Feringa, Ethan N W Howe, Xin Wu, Maxime A Siegler, Philip A Gale. Photomodulation of Transmembrane Transport and Potential by Stiff-Stilbene Based Bis(thio)ureas. Journal of the American Chemical Society. 2022 Jan 12;144(1):331-338