Role of iron ion chelation by quinones in their reduction, OH-radical generation and lipid peroxidation.

Dikalov S, Alov P, Rangelova D
Biochem Biophys Res Commun. 1993 195 (1): 113-9

PMID: 8395821 · DOI:10.1006/bbrc.1993.2017

To study the role of the complex of quinones with iron ions in the processes of quinone reduction and OH-radical generation in the presence of ascorbate (AH) and glutathione (GSH) the quinone-chelators have been used: 2-phenyl-4-butylaminonaphtho[2,3-h]quinolindione-7,12 (Qc) and adriamycin (Adr). 2-Phenyl-5-nitronaphtho[2,3-g]indodione-6,11 (Qn), 2-(3-hydroxypropyl)anthraquinone (AQOP) and 2-dimethylamino-3-chlor-1,4-naphthoquinone (DCNQ) were chosen as quinones that do not chelate iron ions. It was found that, unlike Adr and nonchelating quinones Qn, AQOP, and DCNQ, addition of Qc to AH and GSH leads to semiquinone EPR spectrum formation and OH-radical generation via the complex of Qc with iron ions. It was demonstrated that all these quinones can be reduced by AH. However, reduction constant of Qc-Fe(3+) by the AH was 98 +/- 9 M-1c-1, while DCNQ reduction constant was only 0.042 +/- 0.005 M-1 c-1. It was found that in the presence of GSH only complexes of quinones Qc and Adr with iron ions are reduced. It is concluded that the capability of Qc to reduce and to generate OH-radicals is related to intramolecular electron transfer by the reaction: Fe(2+)-Qc<==>Fe(3+)-Qc. The capability Qc to increase generation of oxygen radicals and to inhibit lipid peroxidation may be interesting for designing quinone-containing antibiotics.

MeSH Terms (12)

Ascorbic Acid Electron Spin Resonance Spectroscopy Free Radicals Glutathione Hydroxides Hydroxyl Radical Iron Iron Chelating Agents Kinetics Lipid Peroxidation Oxidation-Reduction Quinones

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