Catecholates and mixed catecholate hydroxamates as artificial siderophores for mycobacteria |
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| Authors: | Steffen Wittmann Lothar Heinisch Ina Scherlitz-Hofmann Thomas Stoiber Dorothe Ankel-Fuchs Ute Möllmann |
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| Institution: | (1) Hans Knöll-Institute for Natural Products Research, Jena, Germany;(2) Grünenthal GmbH Aachen, Germany;(3) Present address: Jenapharm GmbH & Co. KG, Jena, Germany;(4) Present address: Schering AG, Berlin, Germany;(5) Present address: Institute of Molecular Biotechnology, Jena, Germany |
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| Abstract: | Different mono-, bis- or triscatecholates and mixed mono- or biscatecholate hydroxamates were synthesized as potential siderophores for mycobacteria. Siderophore activity was tested by growth promotion assays using wild type strains and iron transport mutants of mycobacteria as well as Gram-negative bacteria. Some triscatecholates and biscatecholate hydroxamates were active in mutants of Mycobacterium smegmatis deficient in mycobactin and exochelin biosynthesis or exochelin permease, respectively, indicating an uptake route independent of the exochelin/mycobactin pathway. Structure activity relationships were studied. Ampicillin conjugates of some of these compounds were inactive against mycobacteria but active against Gram-negative bacteria. |
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| Keywords: | catecholates Gram-negative bacteria hydroxamates mycobacteria siderophore analogue synthesis |
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