SYNTHESIS AND IRON COMPLEXATION STUDIES OF BIS-HYDROXAMIC ACIDS

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Abstract
A series of bis-hydroxamic acids was prepared by the condensation of the aminoacids glycine, β-alanine, and γ-aminobutyric acid, with succinyl and adipoyl chlorides followed by conversion of the terminal carboxyl groups to hydroxamic acids (HA). Mole ratio plots of iron chelation indicated that 3:1 HA: Fe complexes exist at pH 4 and 6, but that 2:1 HA: Fe complexes are the prevalent species at pH 2. Differences in spacing had little effect on the iron complexing ability as measured through competition equilibria with EDTA. The six bis-hydroxamic acids were subjected to a bioassay screen designed to select compounds possessing in vivo iron removal activity for potential use in treating iron overload in Cooley′s Anemia. All of the six compounds had some activity. The bis-hydroxamic acid derived from succinic acid and γ-aminobutyric acid was particularly active, almost as active as the standard drug desferrioxamine-B.