Thiosquaramides: pH switchable anion transporters

Nathalie Busschaert, Robert B. P. Elmes, Dawid D. Czech, Xin Wu, Isabelle L. Kirby, Evan M. Peck, Kevin D. Hendzel, Scott K. Shaw, Bun Chan, Bradley D. Smith, Katrina A. Jolliffe, Philip A. Gale
  • Chemical Science, January 2014, Royal Society of Chemistry
  • DOI: 10.1039/c4sc01629g

pH switchable anion transport

What is it about?

This paper reports the anion binding and transport properties of thiosquaramides. These compounds are the sulfur analogues of squaramides that have previously been shown to be very effective at mediating the transport of chloride and bicarbonate through lipid bilayers. The work shows that at neutral pH the thiosquaramides are deprotonated and don't function as anion transporters but at more acidic pH they protonate and their anion transport properties are turned on.

Why is it important?

Compounds with pH switchable transport properties have the potential to target cancer cells which are more acidic than healthy cells. So a transporter could disrupt chemical gradients only in the cancer cell thus reducing its toxicity.

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The following have contributed to this page: Professor Philip Gale and Katrina Jolliffe