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Synthesis and antimicrobial activity of an SO2-releasing siderophore conjugate

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JournalJOURNAL OF INORGANIC BIOCHEMISTRY
DateAccepted/In press - 21 May 2022
DateE-pub ahead of print (current) - 1 Jun 2022
DatePublished - Sep 2022
Volume234
Number of pages12
Early online date1/06/22
Original languageEnglish

Abstract

A novel Trojan Horse conjugate consisting of an SO2-releasing 2,4-dinitrobenzenesulfonamide group attached to the monocatecholate siderophore aminochelin was synthesized to examine whether a bidentate catecholate siderophore unit could help potentiate the antimicrobial activity of SO2-releasing prodrugs. The conjugate obtained displays rapid SO2 release on reaction with glutathione, and proved more active against S. aureus than a comparable SO2-releasing prodrug lacking the siderophore unit, although activity required micromolar concentrations. The conjugate was inactive against wild-type E. coli, but activity was observed against an entA mutant strain that is unable to produce its major siderophores. Hence, the poor activity of the conjugate in wild-type E. coli may be due to the production of native siderophores that can compete with the conjugate for iron binding and uptake.

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Copyright © 2022 The Authors. Published by Elsevier Inc. All rights reserved.

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