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Thiosquaramides: pH switchable anion transporters.

Nathalie Busschaert1, Robert B P Elmes2, Dawid D Czech1

  • 1Chemistry, University of Southampton, Southampton, SO17 1BJ, UK.

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|July 7, 2015
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New thiosquaramide molecules mimic biological anion transporters. Their pH-dependent chloride binding and transport activity can be switched ON or OFF, offering potential for synthetic biological systems.

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Area of Science:

  • Supramolecular Chemistry
  • Membrane Transport
  • Synthetic Biology

Background:

  • Cellular anion transport is crucial, mediated by specialized proteins.
  • Synthetic molecules mimicking these transporters are emerging, but few exhibit biological gating behavior.
  • Thiosquaramides present a novel class of synthetic anion transporters.

Purpose of the Study:

  • To synthesize thiosquaramides and investigate their pH-dependent chloride binding.
  • To explore the anion transport capabilities of these compounds.
  • To understand their gating/switching behavior in relation to pH.

Main Methods:

  • Synthesis of thiosquaramide compounds.
  • Nuclear Magnetic Resonance (NMR) titrations for pH-dependent binding studies.
  • Single crystal X-ray diffraction for structural analysis.
  • Vesicle-based assays and spectrophotometric titrations for transport studies.
  • Density Functional Theory (DFT) calculations for acidity analysis.

Main Results:

  • Thiosquaramides exhibit significantly higher acidity (pKa 4.0-9.0) compared to oxosquaramides.
  • At physiological pH (7.2), anion transport is switched OFF due to receptor deprotonation.
  • Transport activity is fully switched ON at lower pH values.
  • Demonstrated pH-dependent chloride binding and transport.

Conclusions:

  • Thiosquaramides function as pH-switchable anion transporters.
  • Their acidity is key to their gating mechanism.
  • These molecules show promise for developing synthetic systems that mimic biological transport with controllable gating.