Black, Conor, Chu, Adrian J, Thomas, Gavin H orcid.org/0000-0002-9763-1313 et al. (2 more authors) (2022) Synthesis and antimicrobial activity of an SO2-releasing siderophore conjugate. JOURNAL OF INORGANIC BIOCHEMISTRY. 111875. ISSN 0162-0134
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.
Metadata
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Copyright, Publisher and Additional Information: | Copyright © 2022 The Authors. Published by Elsevier Inc. All rights reserved. | ||||||
Dates: |
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Institution: | The University of York | ||||||
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) The University of York > Faculty of Sciences (York) > Biology (York) |
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Depositing User: | Pure (York) | ||||||
Date Deposited: | 13 Jun 2022 13:40 | ||||||
Last Modified: | 06 Dec 2023 14:43 | ||||||
Published Version: | https://doi.org/10.1016/j.jinorgbio.2022.111875 | ||||||
Status: | Published | ||||||
Refereed: | Yes | ||||||
Identification Number: | https://doi.org/10.1016/j.jinorgbio.2022.111875 |
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Filename: 1_s2.0_S0162013422001647_main.pdf
Description: 1-s2.0-S0162013422001647-main
Licence: CC-BY 2.5