Involvement of electron and hydrogen transfers through redox metabolism on activity and toxicity of the nimesulide

Borges, Rosivaldo S.; Oliveira, Juliana P.; Matos, Rafaelle Fonseca de; Neto, A. M. J. C.; Carneiro, Agnaldo S.; Monteiro, Marta Chagas

doi:10.1007/s00894-015-2712-3

Cited by 13 publications

(2 citation statements)

References 31 publications

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“…Heterocyclic compounds are well known for their capability to bind free radicals 64 . Furthermore, sulfonamides are known for their redox properties 65 , the 2-pyrazinyl derivative 14 has excellent antioxidant properties. Pyrazine derivatives have the potential to defend cells from oxidative harm caused by ionizing radiation through the transfer of electrons and hydrogen.…”

Section: Resultsmentioning

confidence: 99%

Novel iodoquinazolinones bearing sulfonamide moiety as potential antioxidants and neuroprotectors

Soliman,

Ghorab,

Lotfy

et al. 2023

Sci Rep

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In a search for new antioxidants, a set of new iodoquinazolinone derivatives bearing benzenesulfonamide moiety and variable acetamide pharmacophores 5–17 were designed and synthesized. The structures of the synthesized compounds were confirmed based on spectral data. Compounds 5–17 were screened using in vitro assay for their antioxidant potential and acetylcholinesterase (AChE) inhibitory activity. The 2-(6-iodo-4-oxo-3-(4-sulfamoylphenyl)-3,4-dihydroquinazolin-2-ylthio)-N-(pyrazin-2-yl) acetamide 14 was the most active scaffold with potent AChE inhibitory activity. Compound 14 showed relative safety with a median lethal dose of 300 mg/kg (LD50 = 300 mg/kg), in an acute toxicity study. The possible antioxidant and neuroprotective activities of 14 were evaluated in irradiated mice. Compound 14 possessed in vivo AChE inhibitory activity and was able to modify the brain neurotransmitters. It was able to cause mitigation of gamma radiation-induced oxidative stress verified by the decline in Myeloperoxidase (MPO) and increase of glutathione (GSH) levels. Also, 14 restored the alterations in behavioral tests. Molecular docking of 14 was performed inside MPO and AChE active sites and showed the same binding interactions as that of the co-crystallized ligands considering the binding possibilities and energy scores. These findings would support that 14 could be considered a promising antioxidant with a neuromodulatory effect.

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Section: Resultsmentioning

confidence: 99%

Novel iodoquinazolinones bearing sulfonamide moiety as potential antioxidants and neuroprotectors

Soliman,

Ghorab,

Lotfy

et al. 2023

Sci Rep

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“…e ionization potential (IP(I)) and electron affinity (EA (A)) were descriptors which was calculated as the energy change of the single electron transfer (SET) mechanisms (1) and (2), respectively (reaction (1) in equation (6)) and (reaction (2) in equation 7): energy difference between the product system and the reactant system is defined as proposed by Borges et al [18,19].…”

Section: Computational Detailsmentioning

confidence: 99%

A DFT Analysis on Antioxidant and Antiradical Activities from Anthraquinones Isolated from the Cameroonian Flora

Nyobe

Andiga

Mama

et al. 2019

Journal of Chemistry

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The present work is devoted to the exploration antioxidant and antiradical activity of twenty anthraquinones isolated from the Cameroonian flora at B3LYP/6-311++G(d,p) level of theory using the B3LYP/6-31 + G(d,p) geometrical data as geometry optimization starting points. The single electron transfer mechanism has been adopted to examine both biological activities. The classification of the antiradical profile to integrate the electrodonating power (ω−), electroaccepting power (ω+), donor index (Rd) and acceptor index (Ra) has been performed using the donor-acceptor map (DAM). The antioxidant and radical powers of compounds analyzed have been compared to that of two classical vitamins (vitamin C and gallic acid). The stability of each anthraquinone derivative of the molecular library has been developed according to thermodynamic and kinetic concepts. The global reactivity descriptors (GRDs; electrophilicity index (ω), electronegativity (χ), global softness (S), and global hardness (η)) have been used to analyze the reactivity. The topological analysis of optimized structures indicates that the strength of the hydrogen bonds formed is situated between 44.205 and 52.001 kJ/mol. Our B3LYP results reveal that 3-methoxy-1-vismiaquinone (in a configuration without hydrogen bond) exhibits the best antioxidant capacity in gas phase. A comparison between antioxidant performance of molecules examined and that of classical vitamins (gallic acid, caffeic acid, ferulic acid, and ascorbic acid (vitamin C)) displayed the fact that the single electron transfer (SET) mechanism is more prominent for compounds of the molecular library analyzed. In the same vein, the antiradical behaviors of anthraquinone derivatives have shown to be higher than that of gallic acid and vitamin C in gas phase and water. The 5,8-dihydroxy-2-methylantraquinone structure in a configuration bearing one hydrogen bond has been found to be the best antiradical of the series in aqueous solution.

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Fluorinated Sulfonamides: Synthesis, Characterization, In Silico, Molecular Docking, ADME, DFT Predictions, and Structure‐Activity Relationships, as Well as Assessments of Antimicrobial and Antioxidant Activities

Reheim,

Ghazal,

Abdelhamid

et al. 2024

Drug Development Research

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The design and synthesis of unique two series of fluorinated sulfonamides 3a‐f and 5a‐g utilizing nucleophilic aromatic substitution reactions of tetrafluorophthalonitrile 1 with various sulfonamides 2 under a variety of different reactions conditions were the key goals of the current research. The chemical composition of the generated products has been investigated via mass spectroscopy, 1HNMR, 13CNMR, infrared, and elemental analyzes. Antimicrobial studies were conducted in vitro to evaluate the activity of all new synthesized compounds against resistant strains. The first series showed high potency in very low concentrations. All compounds were studied against DPPH Radical Scavenging Activity and the other series showed high activity even in low molar ratio. In silico molecular docking was used to investigate the potential binding pathways for different receptors: dihydroprotien synthase protein (ID Code: 1AJ0) as an antibacterial and EGFRWT co‐crystallized with erlotinib [PDB ID code 1m17]. Furthermore, synthesized compounds with good ADME predictions to the Lipinski rule of five demonstrated that the recently synthesized compounds had high drug‐likeness qualities when the physicochemical parameter for the most powerful novel candidates was determined. Moreover, the DFT/B3LYP method functionalized with a 6‐31G (d, p) basis set was employed to calculate quantum parameters, MEP analysis, HUMO, and LUMO.

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Involvement of electron and hydrogen transfers through redox metabolism on activity and toxicity of the nimesulide

Cited by 13 publications

References 31 publications

Novel iodoquinazolinones bearing sulfonamide moiety as potential antioxidants and neuroprotectors

Novel iodoquinazolinones bearing sulfonamide moiety as potential antioxidants and neuroprotectors

A DFT Analysis on Antioxidant and Antiradical Activities from Anthraquinones Isolated from the Cameroonian Flora

Fluorinated Sulfonamides: Synthesis, Characterization, In Silico, Molecular Docking, ADME, DFT Predictions, and Structure‐Activity Relationships, as Well as Assessments of Antimicrobial and Antioxidant Activities

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