Synthesis and biological activity of saccharide based lipophilic siderophore mimetics as potential growth promoters for mycobacteria.
Siderophores based on sugar backbones substituted at the 2,3,4- or 2,3,6 positions with hydroxamic or retro-hydroxamic acid chelating units were synthesized and characterized. The alkyl terminus of the iron-coordinating side chain units facilitate lipophilic interactions. Iron coordination properties and complex stability were investigated by ESI-MS and the CAS-Test. The results were correlated to structure activity relationships determined by microbial growth promotion studies under iron limited conditions using wild type strains and iron transport mutants of Mycobacterium smegmatis.
Gebhardt
Peter
P
Biomolecular Chemistry, Leibniz Institute for Natural Products Research and Infection Biology - Hans-Knoell-Institute, Beutenbergstrasse 11a, 07745 Jena, Germany.
Crumbliss
Alvin L
AL
Miller
Marvin J
MJ
Möllmann
Ute
U
D006877:Hydroxamic Acids / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009161:Mycobacterium / Q000187:drug effects* / Q000254:growth & development; D020102:Mycobacterium smegmatis / Q000187:drug effects / Q000254:growth & development; D017262:Siderophores / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D021241:Spectrometry, Mass, Electrospray Ionization
D006877:Hydroxamic Acids; D017262:Siderophores