Synthesis and evaluation of iron chelators with masked hydrophilic moieties

Michael M. Meijler, Rina Arad-Yellin, Z. Ioav Cabantchik, Abraham Shanzer

Research output: Contribution to journalArticlepeer-review

38 Scopus citations

Abstract

Synthetic iron chelators based on the natural siderophore ferrichrome have previously been shown to bind Fe(III) with high affinity (pKf > 27) and have shown no toxicity to mammalian cell cultures in vitro. A new class of lipophilic ferrichrome analogues carrying acetoxymethyl ester moieties has been synthesized. We have shown that these molecules penetrate rapidly through cell membranes and turn highly hydrophilic while inside the cells, upon esterase mediated hydrolysis of the lipophilic termini. The intracellular retention was visualized by labeling these analogues with a fluorescent naphthalic diimide probe. The prohydrophilic iron chelators have been shown to inhibit the metal-catalyzed intracellular formation of reactive oxygen species with high effectivity, and preliminary results suggest these molecules to be potent antimalarial agents.

Original languageEnglish
Pages (from-to)12666-12667
Number of pages2
JournalJournal of the American Chemical Society
Volume124
Issue number43
DOIs
StatePublished - 30 Oct 2002
Externally publishedYes

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