Boosting Anion Transport Activity of Diamidocarbazoles by Electron Withdrawing Substituents

Artificial chloride transporters have been intensely investigated in view of their potential medicinal applications. Recently, we have established 1,8-diamidocarbazoles as a versatile platform for the development of active chloride carriers. In the present contribution, we investigate the influence...

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Bibliographic Details
Published in:Frontiers in chemistry 2021-05, Vol.9, p.690035-690035
Main Authors: Maslowska-Jarzyna, Krystyna, Korczak, Maria L, Chmielewski, Michał J
Format: Article
Language:English
Subjects:
anion transport
Chemistry
chloride transport
liposomes
lucigenin
LUVs
pH-switchable transport
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Summary:Artificial chloride transporters have been intensely investigated in view of their potential medicinal applications. Recently, we have established 1,8-diamidocarbazoles as a versatile platform for the development of active chloride carriers. In the present contribution, we investigate the influence of various electron-withdrawing substituents in positions 3 and 6 of the carbazole core on the chloride transport activity of these anionophores. Using lucigenin assay and large unilamellar vesicles as models, the 3,6-dicyano- and 3,6-dinitro- substituted receptors were found to be highly active and perfectly deliverable chloride transporters, with EC value as low as 22 nM for the Cl /NO exchange. Mechanistic studies revealed that diamidocarbazoles form 1:1 complexes with chloride in lipid bilayers and facilitate chloride/nitrate exchange by carrier mechanism. Furthermore, owing to its increased acidity, the 3,6-dinitro- substituted receptor acts as a pH-switchable transporter, with physiologically relevant apparent pK of 6.4.
ISSN:2296-2646
2296-2646
DOI:10.3389/fchem.2021.690035