Biological and Medicinal Chemistry

Dissecting transmembrane bicarbonate transport by 1,8-di(thio)amidocarbazoles

Authors

  • Krystyna Maslowska-Jarzyna Faculty of Chemistry, Biological and Chemical Research Centre, University of Warsaw, Żwirki i Wigury 101, 02-089 Warsaw, Poland ,
  • Alessio Cataldo Université Libre de Bruxelles, Engineering of Molecular Nano Systems, Ecole Polytechnique de Bruxelles, Avenue F.D. Roosevelt 50, CP165/64, 1050 Brussels, Belgium ,
  • Anna Marszalik Department of Bacterial Physiology, Institute of Microbiology, Faculty of Biology, University of Warsaw, Miecznikowa 1, 02-096 Warsaw, Poland ,
  • Ilona Ignatikova Department of Bacterial Physiology, Institute of Microbiology, Faculty of Biology, University of Warsaw, Miecznikowa 1, 02-096 Warsaw, Poland ,
  • Stephen Butler Loughborough University, Department of Chemistry, Epinal Way, LE11 3TU, Loughborough, United Kingdom ,
  • Radosław Stachowiak Department of Bacterial Physiology, Institute of Microbiology, Faculty of Biology, University of Warsaw, Miecznikowa 1, 02-096 Warsaw, Poland ,
  • Michał J. Chmielewski Faculty of Chemistry, Biological and Chemical Research Centre, University of Warsaw, Żwirki i Wigury 101, 02-089 Warsaw, Poland ,
  • Hennie Valkenier Université Libre de Bruxelles, Engineering of Molecular Nano Systems, Ecole Polytechnique de Bruxelles, Avenue F.D. Roosevelt 50, CP165/64, 1050 Brussels, Belgium

Abstract

Synthetic ionophores able to transport bicarbonate and chloride anions across lipid bilayers are appealing for their wide range of potential biological applications. We have studied the bicarbonate and chloride transport by carbazoles with two amido/thioamido groups using a bicarbonate-sensitive europium(III) probe in liposomes and found a highly remarkable concentration dependence. This can be explained by a combination of two distinct transport mechanisms: HCO3−/Cl− exchange and a combination of unassisted CO2 diffusion and HCl transport, of which the respective contributions were quantified. The compounds studied were found to be highly potent HCl transporters. Based on the mechanistic insights on anion transport, we have tested the antimicrobial activity of these compounds and found good correlation with their ion transport properties and a high activity against Gram-positive bacteria.

Content

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Supplementary material

Thumbnail image of Dissecting transmembrane bicarbonate transport by 1,8-di(thio)amidocarbazoles_ESI.pdf
Dissecting transmembrane bicarbonate transport by 1,8-di(thio)amidocarbazoles
A file containing detailed protocols and results of anion transport studies and biological studies.