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Journal of Trace Elements in Medicine and Biology
Vol. 41, 2017, Pages: 16–22

Desferrioxamine and desferrioxamine-caffeine as carriers of aluminum and gallium to microbes via the Trojan Horse Effect

Jesus Antonio Alvarado Huayhuaz, Hector Aguilar Vitorino, Othon Souto Campos, Silvia Helena Pires Serrano, Telma Mary Kaneko, Breno Pannia Espůsito

Department of Fundamental Chemistry, Institute of Chemistry, University of São Paulo,Av. Prof. Lineu Prestes, 748, 05508-000, São Paulo, SP, Brazil.


Iron acquisition by bacteria and fungi involves in several cases the promiscuous usage of siderophores. Thus, antibiotic resistance from these microorganisms can be circumvented through a strategy of loading toxic metals into siderophores (Trojan Horse Effect). Desferrioxamine (dfo) and its cell-permeant derivative desferrioxamine-caffeine (dfcaf) were complexed with aluminum or gallium for this purpose. The complexes Me(dfo) and Me(dfcaf) (Me = Al3+ and Ga3+) were synthesized and characterized by mass spectroscopy and cyclic voltammetry. Their relative stabilities were studied through competitive equilibria with fluorescent probes calcein, fluorescein-desferrioxamine and 8-hydroxyquinoline. Me(dfo) and Me(dfcaf) were consistently more toxic than free Me3+against Escherichia coliPseudomonas aeruginosaStaphylococcus aureus and Candida albicans, demonstrating the Trojan Horse Effect. Wide spectrum antimicrobial action can be obtained by loading non-essential or toxic metal ions to microbes via a convenient siderophore carrier.

Keywords: Desferrioxamine; Aluminum; Gallium; Caffeine; Trojan horse.

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