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Antioxidant properties and free radical-scavenging reactivity of a family of hydroxynaphthalenones and dihydroxyanthracenones
- Source :
- Bioorganic & Medicinal Chemistry. 15:7058-7065
- Publication Year :
- 2007
- Publisher :
- Elsevier BV, 2007.
-
Abstract
- This study was undertaken to investigate the free radical-scavenging and antioxidant activities of various structurally related hydroquinones including hydroxynaphthalenones and dihydroxyanthracenones. Electron spin resonance spectroscopy and spin trapping techniques were used to evaluate the ability of hydroquinones to scavenge hydroxyl, diphenylpicrylhydrazyl, and galvinoxyl radicals. In addition, the oxygen radical absorbing capacity assay using fluorescein (ORAC-FL) was used to obtain the relative antioxidant capacity of these radicals. The rate constants of the first H atom abstraction by 2,2-diphenyl-2-picrylhydrazyl ( k 2 ), were obtained under pseudo-first-order conditions. The free radical-scavenging activities and k 2 values discriminate well between hydroxynaphthalenones and dihydroxyanthracenones, showing that the latter have better antioxidant properties. The aforementioned experimental data agree with quantum-chemical results demonstrating the relevance of intramolecular H bonding to radical-scavenging activities.
- Subjects :
- Antioxidant
DPPH
Radical
medicine.medical_treatment
Clinical Biochemistry
Pharmaceutical Science
Naphthalenes
Photochemistry
Sensitivity and Specificity
Biochemistry
Antioxidants
law.invention
Mice
chemistry.chemical_compound
Galvinoxyl
law
Cell Line, Tumor
Drug Discovery
medicine
Animals
Organic chemistry
Reactivity (chemistry)
Electron paramagnetic resonance
Molecular Biology
Anthracenes
Molecular Structure
Hydroquinone
Spin trapping
Organic Chemistry
Electron Spin Resonance Spectroscopy
Reproducibility of Results
Hydrogen Bonding
Free Radical Scavengers
Oxygen
Kinetics
chemistry
Molecular Medicine
Reactive Oxygen Species
Subjects
Details
- ISSN :
- 09680896
- Volume :
- 15
- Database :
- OpenAIRE
- Journal :
- Bioorganic & Medicinal Chemistry
- Accession number :
- edsair.doi.dedup.....e03b0493972ad73dd51a6033e2080724