Solvent effects on the antioxidant activity of 3,4-dihydroxyphenylpyruvic acid : DFT and TD-DFT studies

Fifen, Jean Jules; Nsangou, Mama; Dhaouadi, Zoubeida; Motapon, Ousmanou; Jaı̈dane, N.

doi:10.1016/j.comptc.2011.03.006

Cited by 86 publications

(63 citation statements)

References 76 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Hence, in contrast to the results published before (the scavenging of hydroxyl radical by DHPPA is governed by CPCET in nonpolar solvents and PT-ET mechanisms in polar solvents [3]), PT-ET mechanism may no longer be favored in polar solvents if coreactive species are taken into account.…”

Section: Pcet and Pt Mechanisms Via Somos Npascontrasting

confidence: 53%

“…Therefrom, it is noteworthy that the scavenging of hydroxyl radical by 3,4-DHPPA passes through a transition state (TS) while that of OBr − anion is barrierless. Moreover, it is well-known that the reaction of a phenolic acid (PhA) with neutral ROS leads to PCET mechanism while that with negatively charged ROS undergoes a barrierless PT mechanism [3,12,18,43,44]. This result may be generalized to PhAs which only have carbon, oxygen, and hydrogen in their skeleton (e.g., Quercetin may be a good candidate) and are involving the same RS or other.…”

Section: Resultsmentioning

confidence: 93%

“…Solvation free energies of the electron, proton, and hydrogen atom are, respectively, the free energies change of reactions below [3]: (21) where solvent (solv) represents a molecule of solvent in its cavity, X (solv) means that X is solvated, and solvent may be one of those used in this work. So, "solv" stands for cyclohexane, benzene, and so forth.…”

Section: Solvation Free Energies Of the Electron Protonmentioning

confidence: 99%

“…It is quite always an open problem. Recently, we studied the 3,4-dihydroxyphenylpyruvic acid (3,4-DHPPA) O-H bond cleavage in various media [3]. The scheme used in such a work does not consider the coreactive species (molecules or atoms which receive the transferred proton or hydrogen atom).…”

Section: Introductionmentioning

confidence: 99%

“…Moreover, metal ions effects on the antioxidant activity of 3,4-DHPPA were studied in the vacuum [18]. A conformational study of this acid was also undertaken [3] and the likeliest conformer is depicted in Figure 1. The…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Proton-Coupled Electron Transfer in the Reaction of 3,4-Dihydroxyphenylpyruvic Acid with Reactive Species in Various Media

Fifen

Dhaouadi

Nsangou

et al. 2015

International Journal of Chemical Physics

Self Cite

View full text Add to dashboard Cite

The distinction of concerted proton-coupled electron transfer (CPCET) from sequential one as well as proton transfer-electron transfer (PT-ET) from electron transfer-proton transfer (ET-PT) in the O-H bond cleavage reactions in various media has always been a difficult task. In this work, the activation barrier of the CPCET mechanism, its rate constants, and reaction free energies related to ET-PT and PT-ET involving coreactive species were presented as good parameters to attempt the problem. DFT calculations were carried out studying the described pathways subsequent to the scavenging of• OH and OBr − by the 3,4-DHPPA in various media. The solvation was described in a hybrid manner using IEF-PCM model conjointly with a model that takes into account some solute-solvent interactions. As a result, we found that the scavenging of hydroxyl radical by 3,4-DHPPA is thermodynamically governed by a one-step hydrogen atom transfer (CPCET) from the acid to the radical in all media. In kinetic viewpoint, CPCET still dominates in the vacuum and in nonpolar solvents, but in polar solvents it could compete strongly with the ET-PT mechanism so that the latter could slightly dominate.

show abstract

Section: Pcet and Pt Mechanisms Via Somos Npascontrasting

confidence: 53%

Section: Resultsmentioning

confidence: 93%

Section: Solvation Free Energies Of the Electron Protonmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Proton-Coupled Electron Transfer in the Reaction of 3,4-Dihydroxyphenylpyruvic Acid with Reactive Species in Various Media

Fifen

Dhaouadi

Nsangou

et al. 2015

International Journal of Chemical Physics

Self Cite

View full text Add to dashboard Cite

show abstract

Microwave‐Assisted Fe₃O₄ Nanoparticles Catalyzed Cascade Synthesis of 3‐(1,4,5‐Triaryl‐1H‐imidazol‐2yl)quinolin‐2‐amines as COX‐1, COX‐2 Inhibitors and Antioxidant Agents

Bheemayya,

Kamble,

Shettar

et al. 2024

Applied Organom Chemis

View full text Add to dashboard Cite

A proficient Fe3O4 nanoparticle catalyzed cascade multicomponent synthetic protocol has been established to synthesize the title compounds. 2‐Chloroquinoline‐3‐carbaldehydes, aniline, and substituted benzils were subjected to cascade coupling to produce novel 3‐(1,4,5‐triaryl‐1H‐imidazol‐2‐yl)quinolin‐2‐amine 5k–z under microwave irradiation using Fe3O4 NPs. According to the biological data and the computational analysis, the compounds were found to bind COX‐2 enzyme superior than the COX‐1 enzyme. The molecular docked positions of the compounds (PDB ID: 4O1Z and PDB ID: 5IKR; A chain) were examined, and the results showed that these configurations are similar to those of the highly selective COX‐1 and COX‐2 inhibitors. Compared to mefenamic acid (1.318 μg), the compounds 5k, 5l, 5n, 5p, 5q, 5r, 5s, 5t, 5v, 5x, and 5z Showed IC50 values of 1.172, 1.136, 1.508, 1.0373, 1.186, 1.017, 1.827, 1.008, 1.504, 1.217, 1.440, and 1.832, respectively, making them the most effective and selective COX‐1 and COX‐2 inhibitors. For every significantly active molecule, a selectivity index was calculated. Interestingly, these molecules that worked as COX inhibitors also functioned well and showed promising results for antioxidant activity.

show abstract

Large‐Sized Ammonia Clusters and Solvation Energies of the Proton in Ammonia

2019

View full text Add to dashboard Cite

The absolute solvation energies (free energies and enthalpies) of the proton in ammonia are used to compute the pKa of species embedded in ammonia. They are also used to compute the solvation energies of other ions in ammonia. Despite their importance, it is not possible to determine experimentally the solvation energies of the proton in a given solvent. We propose in this work a direct approach to compute the solvation energies of the proton in ammonia from large‐sized neutral and protonated ammonia clusters. To undertake this investigation, we performed a geometry optimization of neutral and protonated ammonia 30‐mer, 40‐mer, and 50 mer to locate stable structures. These structures have been fully optimized at both APFD/6‐31++g(d,p) and M06‐2X/6‐31++g(d,p) levels of theory. An infrared spectroscopic study of these structures has been provided to assess the reliability of our investigation. Using these structures, we have computed the absolute solvation free energy and the absolute solvation enthalpy of the proton in ammonia. It comes out that the absolute solvation free energy of the proton in ammonia is calculated to be −1192 kJ mol–1, whereas the absolute solvation enthalpy is evaluated to be −1214 kJ mol–1. © 2019 Wiley Periodicals, Inc.

show abstract

Solvent effects on the antioxidant activity of 3,4-dihydroxyphenylpyruvic acid : DFT and TD-DFT studies

Cited by 86 publications

References 76 publications

Proton-Coupled Electron Transfer in the Reaction of 3,4-Dihydroxyphenylpyruvic Acid with Reactive Species in Various Media

Proton-Coupled Electron Transfer in the Reaction of 3,4-Dihydroxyphenylpyruvic Acid with Reactive Species in Various Media

Microwave‐Assisted Fe₃O₄ Nanoparticles Catalyzed Cascade Synthesis of 3‐(1,4,5‐Triaryl‐1H‐imidazol‐2yl)quinolin‐2‐amines as COX‐1, COX‐2 Inhibitors and Antioxidant Agents

Large‐Sized Ammonia Clusters and Solvation Energies of the Proton in Ammonia

Contact Info

Product

Resources

About

Solvent effects on the antioxidant activity of 3,4-dihydroxyphenylpyruvic acid : DFT and TD-DFT studies

Cited by 86 publications

References 76 publications

Proton-Coupled Electron Transfer in the Reaction of 3,4-Dihydroxyphenylpyruvic Acid with Reactive Species in Various Media

Proton-Coupled Electron Transfer in the Reaction of 3,4-Dihydroxyphenylpyruvic Acid with Reactive Species in Various Media

Microwave‐Assisted Fe3O4 Nanoparticles Catalyzed Cascade Synthesis of 3‐(1,4,5‐Triaryl‐1H‐imidazol‐2yl)quinolin‐2‐amines as COX‐1, COX‐2 Inhibitors and Antioxidant Agents

Large‐Sized Ammonia Clusters and Solvation Energies of the Proton in Ammonia

Contact Info

Product

Resources

About

Microwave‐Assisted Fe₃O₄ Nanoparticles Catalyzed Cascade Synthesis of 3‐(1,4,5‐Triaryl‐1H‐imidazol‐2yl)quinolin‐2‐amines as COX‐1, COX‐2 Inhibitors and Antioxidant Agents