Effect of Methoxy Substituents on the Activation Barriers of the Glutathione Peroxidase-Like Mechanism of an Aromatic Cyclic Seleninate

Density functional theory (DFT) models including explicit water molecules have been used to model the redox scavenging mechanism of aromatic cyclic seleninates. Experimental studies have shown that methoxy substitutions affect the rate of scavenging of reactive oxygen species differently depending u...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2015-06, Vol.20 (6), p.10244-10252
Main Authors: Bayse, Craig A, Shoaf, Ashley L
Format: Article
Language:English
Subjects:
antioxidants
density functional theory
Free Radical Scavengers - chemistry
glutathione peroxidase
Glutathione Peroxidase - chemistry
Methyl Ethers - chemistry
Molecular Mimicry
organoselenium compounds
Organoselenium Compounds - chemistry
Oxidation
Oxidation-Reduction
Quantum Theory
Reactive Oxygen Species - antagonists & inhibitors
Reactive Oxygen Species - chemistry
Selenium
Solvents
Sulfides - chemistry
Thermodynamics
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Summary:Density functional theory (DFT) models including explicit water molecules have been used to model the redox scavenging mechanism of aromatic cyclic seleninates. Experimental studies have shown that methoxy substitutions affect the rate of scavenging of reactive oxygen species differently depending upon the position. Activities are enhanced in the para position, unaffected in the meta, and decreased in the ortho. DFT calculations show that the activation barrier for the oxidation of the selenenyl sulfide, a proposed key intermediate, is higher for the ortho methoxy derivative than for other positions, consistent with the low experimental conversion rate.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules200610244