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

Publication ,  Journal Article
Charkoudian, LK; Pham, DM; Franz, KJ
Published in: Journal of the American Chemical Society
September 2006

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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Published In

Journal of the American Chemical Society

DOI

EISSN

1520-5126

ISSN

0002-7863

Publication Date

September 2006

Volume

128

Issue

38

Start / End Page

12424 / 12425

Related Subject Headings

  • Spectrophotometry, Ultraviolet
  • Prodrugs
  • Oxidation-Reduction
  • Isonicotinic Acids
  • Iron Chelating Agents
  • Iron
  • Hydroxyl Radical
  • Hydrogen Peroxide
  • Hydrazones
  • General Chemistry
 

Citation

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Charkoudian, L. K., Pham, D. M., & Franz, K. J. (2006). A pro-chelator triggered by hydrogen peroxide inhibits iron-promoted hydroxyl radical formation. Journal of the American Chemical Society, 128(38), 12424–12425. https://doi.org/10.1021/ja064806w
Charkoudian, Louise K., David M. Pham, and Katherine J. Franz. “A pro-chelator triggered by hydrogen peroxide inhibits iron-promoted hydroxyl radical formation.Journal of the American Chemical Society 128, no. 38 (September 2006): 12424–25. https://doi.org/10.1021/ja064806w.
Charkoudian LK, Pham DM, Franz KJ. A pro-chelator triggered by hydrogen peroxide inhibits iron-promoted hydroxyl radical formation. Journal of the American Chemical Society. 2006 Sep;128(38):12424–5.
Charkoudian, Louise K., et al. “A pro-chelator triggered by hydrogen peroxide inhibits iron-promoted hydroxyl radical formation.Journal of the American Chemical Society, vol. 128, no. 38, Sept. 2006, pp. 12424–25. Epmc, doi:10.1021/ja064806w.
Charkoudian LK, Pham DM, Franz KJ. A pro-chelator triggered by hydrogen peroxide inhibits iron-promoted hydroxyl radical formation. Journal of the American Chemical Society. 2006 Sep;128(38):12424–12425.
Journal cover image

Published In

Journal of the American Chemical Society

DOI

EISSN

1520-5126

ISSN

0002-7863

Publication Date

September 2006

Volume

128

Issue

38

Start / End Page

12424 / 12425

Related Subject Headings

  • Spectrophotometry, Ultraviolet
  • Prodrugs
  • Oxidation-Reduction
  • Isonicotinic Acids
  • Iron Chelating Agents
  • Iron
  • Hydroxyl Radical
  • Hydrogen Peroxide
  • Hydrazones
  • General Chemistry