A new route to trihydroxamate-containing artificial siderophores and synthesis of a new fluorescent probe

A new trihydroxamate-containing amine was synthesized and was used to have access to a fluorescent labelled artificial siderophore. It behaves as a ferrichrome analogue in various organisms and particularly in Candida albicans. A fluorescent labelled artificial siderophore 1 was synthesized by coupl...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2005-03, Vol.13 (5), p.1799-1803
Main Authors: Ouchetto, H., Dias, M., Mornet, R., Lesuisse, E., Camadro, J.-M.
Format: Article
Language:English
Subjects:
Biological and medical sciences
Chemical Sciences
Ferrichrome - chemical synthesis
Ferrichrome - pharmacology
Fluorescent Dyes - chemical synthesis
Fluorescent Dyes - pharmacology
Fundamental and applied biological sciences. Psychology
Growth, nutrition, metabolism, transports, enzymes. Molecular biology
Hydroxamic Acids - chemistry
Iron Chelating Agents - chemistry
Magnetic Resonance Spectroscopy
Mass Spectrometry - methods
Material chemistry
Microbiology
Mycology
Siderophores - chemistry
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Summary:A new trihydroxamate-containing amine was synthesized and was used to have access to a fluorescent labelled artificial siderophore. It behaves as a ferrichrome analogue in various organisms and particularly in Candida albicans. A fluorescent labelled artificial siderophore 1 was synthesized by coupling a 7-nitrobenz-2-oxa-1,3-diazole (NBD) derivative to the terminal amino group of a new trihydroxamate-containing amine 2, a ferrichrome-type siderophore that was obtained from tris(hydroxymethyl)aminomethane. Compound 1 was shown to be a suitable tool for experiments on siderophore transport and uptake processes in various organisms cells and particularly in Candida albicans cells.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2004.11.053