A pro-chelator triggered by hydrogen peroxide inhibits iron-promoted hydroxyl radical formation.

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 27, 2006

Published In

Volume / Issue

  • 128 / 38

Start / End Page

  • 12424 - 12425

PubMed ID

  • 16984186

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja064806w

Language

  • eng

Conference Location

  • United States