Publications [#232711] of Katherine J. Franz

Journal Articles

  1. Charkoudian, LK; Pham, DM; Franz, KJ, "A pro-chelator triggered by hydrogen peroxide inhibits iron-promoted hydroxyl radical formation.", Journal of the American Chemical SocietySeptember,, 2006, 128(38), 12424-12425 [16984186], [doi].
    (last updated on 2023/01/01)

    Abstract:
    The synthesis and structural characterization of a new pro-chelating agent, isonicotinic acid [2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzylidene]-hydrazide (BSIH), are presented. BSIH only weakly interacts with iron unless hydrogen peroxide (H2O2) is present to remove the boronic ester protecting group to reveal a phenol that is a key metal-binding group of tridentate salicylaldehyde isonicotinoyl hydrazone (SIH). BSIH prevents deoxyribose degradation caused by hydroxyl radicals that are generated from H2O2 and redox-active iron by sequestering Fe3+ and preventing iron-promoted hydroxyl radical formation. The rate-determining step for iron sequestration is conversion of BSIH to SIH, followed by rapid Fe3+ complexation. The pro-chelate approach of BSIH represents a promising strategy for chelating a specific pool of detrimental metal ions without disturbing healthy metal ion distribution.