Hydroxamate siderophores: natural occurrence, chemical synthesis, iron binding affinity and use as Trojan horses against pathogens.
File(s)
Author(s)
Al Shaer, Danah
Almusaimi, Othman
de la Torre, Beatriz G
Albericio, Fernando
Type
Journal Article
Abstract
Hydroxamic acids are an important class of molecules, in particular because of their metal-chelating ability. Microorganisms, including pathogenic bacteria, use hydroxamate-based entities (siderophores), among others, to acquire Fe (III). The "Trojan horse" strategy exploits the need of bacteria for this metal by using Fe (III) active transporters to carry antibacterial or bactericidal moieties into the bacterial cell. Many natural Trojan horses (sideromycins) are derived from hydroxamic acids, thereby reflecting their potency. Various artificial sideromycins and their antibacterial activities have been reported. This review discusses the structural aspects of the hydroxamate-siderophores isolated in the last two decades, the chemical synthesis of their building blocks, their binding affinity towards Fe (III), and their application as Trojan horses (weaknesses and strengths).
Date Issued
2020-12-15
Date Acceptance
2020-08-24
Citation
European Journal of Medicinal Chemistry, 2020, 208, pp.1-31
ISSN
0223-5234
Publisher
Elsevier
Start Page
1
End Page
31
Journal / Book Title
European Journal of Medicinal Chemistry
Volume
208
Copyright Statement
© 2020 Elsevier Masson SAS. All rights reserved. This manuscript is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International Licence http://creativecommons.org/licenses/by-nc-nd/4.0/
Identifier
https://www.ncbi.nlm.nih.gov/pubmed/32947228
PII: S0223-5234(20)30763-7
Subjects
Fe (III) binding affinity
Hydroxamate
Sideromycins
Siderophore
Siderophore-drug conjugate
Trojan horse
Publication Status
Published
Coverage Spatial
France
Article Number
ARTN 112791
Date Publish Online
2020-09-05