IRON(III)-CHELATING RESINS .3. SYNTHESIS, IRON(III)-CHELATING PROPERTIES, AND IN-VITRO ANTIBACTERIAL ACTIVITY OF COMPOUNDS CONTAINING 3-HYDROXY-2-METHYL-4(1H)-PYRIDINONE LIGANDS

The synthesis, iron(III)-chelating properties, and antibacterial activity of several compounds containing the 3-hydroxy-2-methyl-4(1H)-pyridinone (HMP) moiety are described. Using the HMP derivatives iron(III) could be mobilized from iron(III)-binding proteins at physiological pH with a rate order of transferrin > lactoferrin > ferritin. Addition of HMP-containing compounds to a growth medium at a concentration of 20 mM/L resulted in a complete inhibition of the growth of Escherichia coli and about 90 % inhibition for Listeria inocua after 7 h of incubation at 37-degrees-C. After inhibition of bacteria growth by the HMP derivatives growth started again when ferric ions were added to the medium, which implies that the antibacterial activity is due to a limitation of iron available to the organisms.