A pro-chelator triggered by hydrogen peroxide inhibits iron-promoted hydroxyl radical formation.
Journal Article (Journal Article)
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.
Full Text
Duke Authors
Cited Authors
- Charkoudian, LK; Pham, DM; Franz, KJ
Published Date
- September 2006
Published In
Volume / Issue
- 128 / 38
Start / End Page
- 12424 - 12425
PubMed ID
- 16984186
Electronic International Standard Serial Number (EISSN)
- 1520-5126
International Standard Serial Number (ISSN)
- 0002-7863
Digital Object Identifier (DOI)
- 10.1021/ja064806w
Language
- eng