A pro-chelator triggered by hydrogen peroxide inhibits iron-promoted hydroxyl radical formation |
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Authors: | Charkoudian Louise K Pham David M Franz Katherine J |
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Institution: | Department of Chemistry, Duke University, P.O. Box 90346, Durham, North Carolina 27708, USA. |
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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. |
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