Issue 38, 2022

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

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 transporter 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 a good correlation with their ion transport properties and a high activity against Gram-positive bacteria.

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

Supplementary files

Article information

Article type
Paper
Submitted
10 8 2022
Accepted
12 9 2022
First published
16 9 2022

Org. Biomol. Chem., 2022,20, 7658-7663

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

K. Maslowska-Jarzyna, A. Cataldo, A. Marszalik, I. Ignatikova, S. J. Butler, R. Stachowiak, M. J. Chmielewski and H. Valkenier, Org. Biomol. Chem., 2022, 20, 7658 DOI: 10.1039/D2OB01461K

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