A Pro-chelator Triggered by Hydrogen Peroxide inhibits Iron-Promoted Hydroxyl Radical Formation
Document Type
Journal Article
Role
Author
Publisher
American Chemical Society
Journal Title
Journal of the American Chemical Society
Volume
128
Issue
38
First Page
12424
Last Page
12425
Publication Date
9-27-2006
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.
Repository Citation
Charkoudian, Louise; Pham, David M.; and Franz, Katherine J., "A Pro-chelator Triggered by Hydrogen Peroxide inhibits Iron-Promoted Hydroxyl Radical Formation" (2006). Faculty Publications. Paper 527.