Influence of the Structure on the Antioxidant Activity of Tetradentate Schiff Bases and their Copper(II) Complexes: Possible Mechanisms

The influence of the structure on the antioxidant activity of a series of Schiff bases and their copper(II) complexes as well as possible mechanisms of antioxidant activity were investigated. Schiff bases are derived from the condensation of ethane-1,2-diamine or propane-1,2-diamine and pentane-2,4-...

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Veröffentlicht in:Journal of the Brazilian Chemical Society 2013-08, Vol.24 (8), p.1322-1328
Hauptverfasser: Aburas, Najat M., Stevanović, Nikola R., Milčić, Miloš K., Đ. Lolić, Aleksandar, Natić, Maja M., Tešić, Živoslav Lj, Baošić, Rada M.
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Sprache:eng
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Zusammenfassung:The influence of the structure on the antioxidant activity of a series of Schiff bases and their copper(II) complexes as well as possible mechanisms of antioxidant activity were investigated. Schiff bases are derived from the condensation of ethane-1,2-diamine or propane-1,2-diamine and pentane-2,4-dione and/or 1-phenylbutane-1,3-dione. The corresponding complexes were synthesized. The antioxidant activity in vitro, determined using reversed-phase thin layer chromatography assay (RP TLC) based on the reaction with 2,2'-diphenyl-1-picrylhydrazyl, was expressed as Trolox equivalent antioxidant capacity (TEAC). The influence of the structure was observed on the basis of interpretable and informative descriptors calculated by hybrid density functional theory (DFT) methods. Structural features responsible for the antioxidant activity of the investigated compounds were discussed. Copper(II) complexes showed a significantly higher antioxidant activity than their corresponding ligands. Calculated quantum-chemical descriptors gave an insight to the reaction mechanism of the scavenging/antioxidant activity of tetradentate Schiff bases and their copper(II) complexes and two different reaction mechanisms were proposed.
ISSN:0103-5053
1678-4790
DOI:10.5935/0103-5053.20130167