ArticleJournal of molecular modeling2012
Quantum-chemical investigation of the structure and the antioxidant properties of α-lipoic acid and its metabolites.
Article in Journal of molecular modeling, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed, 99 citations in OpenAlex.
- Therapeutic Potential of Alpha-Lipoic Acid: Unraveling Its Role in Oxidative Stress and Inflammatory Conditions.Current issues in molecular biology · 2025Review
- Elucidating the antioxidant potential of some flavanones as MAO-B inhibitors through DAM, in silico molecular docking and computational analysis.Plant molecular biology · 2025Article
- A DFT analysis of the antioxidant capacity of scopolin and scopoletin.Journal of molecular modeling · 2024Article
- Alpha-Lipoic Acid: Biological Mechanisms and Health Benefits.Antioxidants (Basel, Switzerland) · 2024Review
- Density Functional Theory Studies on the Chemical Reactivity of Allyl Mercaptan and Its Derivatives.Molecules (Basel, Switzerland) · 2024Article
- Alpha-lipoic acid supplementation corrects pathological alterations in cellular models of pantothenate kinase-associated neurodegeneration with residual PANK2 expression levels.Orphanet journal of rare diseases · 2023Article
- Article
- Alpha-Lipoic Acid as an Antioxidant Strategy for Managing Neuropathic Pain.Antioxidants (Basel, Switzerland) · 2022Review
- Targeting hepatic sulfane sulfur/hydrogen sulfide signaling pathway with α-lipoic acid to prevent diabetes-induced liver injury via upregulating hepatic CSE/3-MST expression.Diabetology & metabolic syndrome · 2022Article
- Modulation of COX-2 and NADPH oxidase-4 by alpha-lipoic acid ameliorates busulfan-induced pulmonary injury in rats.Heliyon · 2021Article
- Natural Antioxidant Application on Fat Accumulation: Preclinical Evidence.Antioxidants (Basel, Switzerland) · 2021Review
- Ligand-based design of chalcone analogues and thermodynamic analysis of their mechanism of free radical scavenge.Journal of molecular modeling · 2021Article
- Toxicological Profile of the Pain-Relieving Antioxidant Compound Thioctic Acid in Its Racemic and Enantiomeric Forms.Antioxidants (Basel, Switzerland) · 2020Article
- A theoretical evaluation on free radical scavenging activity of 3-styrylchromone derivatives: the DFT study.Journal of molecular modeling · 2020Article
- Structure-antioxidant activity relationship of methoxy, phenolic hydroxyl, and carboxylic acid groups of phenolic acids.Scientific reports · 2020Article
- Insights on the Use of α-Lipoic Acid for Therapeutic Purposes.Biomolecules · 2019Review
- Article
- Comparative Study of Antioxidant Potential of Selected Dietary Vitamins; Computational Insights.Molecules (Basel, Switzerland) · 2019Article
- Protein lipoylation: an evolutionarily conserved metabolic regulator of health and disease.Current opinion in chemical biology · 2018Review
- Organic-inorganic hybrid nanoparticles for bacterial inhibition: synthesis and characterization of doped and undoped ONPs with Ag/Au NPs.Molecules (Basel, Switzerland) · 2015Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Quantum-chemical computations were used to investigate the structure-antioxidant parameter relationships of α-lipoic acid and its natural metabolites bisnorlipoic acid and tetranorlipoic acid in their oxidized and reduced forms. The enantiomers of lipoic and dihydrolipoic acid were optimized using the B3LYP/6-311+G(3df,2p), B3LYP/aug-cc-pVDZ and MP2(full)/6-31+G(d,p) levels of theory as isolated molecules and in the presence of water. The geometries of the metabolites and the values of their antioxidant parameters (proton affinity, bond dissociation enthalpy, adiabatic ionization potential, spin density, and the highest occupied molecular orbital energy) were calculated at the B3LYP/6-311+G(3df,2p) level of theory. The results obtained reveal similarities between these structures: a pentatomic, nonaromatic ring is present in the oxidized forms, while an unbranched aliphatic chain (as found in saturated fatty acids) is present in both the oxidized and the reduced forms. Analysis of the spin density and the highest occupied molecular orbital energy revealed that the SH groups exhibited the greatest electron-donating activities. The values obtained for the proton affinity, bond dissociation enthalpy and adiabatic ionization potential indicate that the preferred antioxidant mechanisms for α-lipoic acid and its metabolites are sequential proton loss electron transfer in polar media and hydrogen atom transfer in vacuum.
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