Theoretical and Computational Chemistry in Antioxidant Research

A special issue of Antioxidants (ISSN 2076-3921).

Deadline for manuscript submissions: closed (30 November 2023) | Viewed by 3742

Special Issue Editors


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Guest Editor
Department of Chemistry and Chemical Technologies, Università della Calabria, Via P. Bucci, Ponte Bucci cubo 14c, 87036 Rende, CS, Italy
Interests: theoretical and computational methods; reaction mechanism; oxidative stress; excited states
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Guest Editor
Dipartimento di Chimica e Tecnologie Chimiche, Università Della Calabria, Via P. Bucci, Cubo 12/D, I-87030 Rende, CS, Italy
Interests: computational chemistry; catalysis; antioxidants; bio-inorganic chemistry
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

The main aim of this Special Issue is to offer an overview of the potentiality of modern theoretical and computational methods to elucidate structural, electronic, spectroscopic, kinetic, and biomolecular properties of natural and newly synthetized antioxidant systems and their interactions with radicals. Contributions on acid-base equilibria in water, reaction mechanisms, metal chelation, Fenton reaction behaviors, enzyme inhibition, dynamical behaviors, new methods and computational procedures, de novo drug design, and reactivity indices are welcome, as well as other theoretical and computational aspects on the properties and antioxidant working mechanisms.

Prof. Dr. Nino Russo
Dr. Mario Prejanò
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Antioxidants is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2900 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • density functional theory
  • ab initio
  • computational chemistry
  • antioxidant solution equilibria
  • antioxidant reaction mechanisms
  • metal chelation
  • antioxidant enzyme inhibition
  • molecular docking
  • molecular dynamics
  • kinetic constants
  • reactive oxygen species
  • radicals
  • polyphenols

Published Papers (3 papers)

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Research

17 pages, 1526 KiB  
Article
Coumarin N-Acylhydrazone Derivatives: Green Synthesis and Antioxidant Potential—Experimental and Theoretical Study
by Dušica M. Simijonović, Dejan A. Milenković, Edina H. Avdović, Žiko B. Milanović, Marko R. Antonijević, Ana D. Amić, Zana Dolićanin and Zoran S. Marković
Antioxidants 2023, 12(10), 1858; https://doi.org/10.3390/antiox12101858 - 13 Oct 2023
Viewed by 948
Abstract
Coumarin N-acylhydrazone derivatives were synthesized in the reaction of 3-acetylcoumarin and different benzohydrazides in the presence of molecular iodine as catalyst and at room temperature. All reactions were rapidly completed, and products were obtained in good to excellent yields. It is important [...] Read more.
Coumarin N-acylhydrazone derivatives were synthesized in the reaction of 3-acetylcoumarin and different benzohydrazides in the presence of molecular iodine as catalyst and at room temperature. All reactions were rapidly completed, and products were obtained in good to excellent yields. It is important to emphasize that four products were reported for the first time in this study. The obtained compounds were subjected to evaluation of their in vitro antioxidative activity using DPPH, ABTS, and FRAP methods. It was shown that products with a catechol moiety in their structure are the most potent antioxidant agents. The thermodynamic parameters and Gibbs free energies of reactions were used to determine the most probable mechanism of action. The results of in silico examination emphasize the need to take solvent polarity and free radical species into account when examining antiradical action. It was discovered by using computational approaches that HAT and SPLET are competitive molecular pathways for the radical scavenging activity of all compounds in polar mediums, while the HAT is the dominant mechanism in non-polar environments. Full article
(This article belongs to the Special Issue Theoretical and Computational Chemistry in Antioxidant Research)
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18 pages, 11534 KiB  
Article
Exploring the Antioxidant Properties of Caffeoylquinic and Feruloylquinic Acids: A Computational Study on Hydroperoxyl Radical Scavenging and Xanthine Oxidase Inhibition
by Houssem Boulebd, Miguel Carmena-Bargueño and Horacio Pérez-Sánchez
Antioxidants 2023, 12(9), 1669; https://doi.org/10.3390/antiox12091669 - 25 Aug 2023
Cited by 1 | Viewed by 1087
Abstract
Caffeoylquinic (5-CQA) and feruloylquinic (5-FQA) acids, found in coffee and other plant sources, are known to exhibit diverse biological activities, including potential antioxidant effects. However, the underlying mechanisms of these phenolic compounds remain elusive. This paper investigates the capacity and mode of action [...] Read more.
Caffeoylquinic (5-CQA) and feruloylquinic (5-FQA) acids, found in coffee and other plant sources, are known to exhibit diverse biological activities, including potential antioxidant effects. However, the underlying mechanisms of these phenolic compounds remain elusive. This paper investigates the capacity and mode of action of 5-CQA and 5-FQA as natural antioxidants acting as hydroperoxyl radical scavengers and xanthine oxidase (XO) inhibitors. The hydroperoxyl radical scavenging potential was investigated using thermodynamic and kinetic calculations based on the DFT method, taking into account the influence of physiological conditions. Blind docking and molecular dynamics simulations were used to investigate the inhibition capacity toward the XO enzyme. The results showed that 5-CQA and 5-FQA exhibit potent hydroperoxyl radical scavenging capacity in both polar and lipidic physiological media, with rate constants higher than those of common antioxidants, such as Trolox and BHT. 5-CQA carrying catechol moiety was found to be more potent than 5-FQA in both physiological environments. Furthermore, both compounds show good affinity with the active site of the XO enzyme and form stable complexes. The hydrogen atom transfer (HAT) mechanism was found to be exclusive in lipid media, while both HAT and SET (single electron transfer) mechanisms are possible in water. 5-CQA and 5-FQA may, therefore, be considered potent natural antioxidants with potential health benefits. Full article
(This article belongs to the Special Issue Theoretical and Computational Chemistry in Antioxidant Research)
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17 pages, 2191 KiB  
Article
A DFT Study on the Kinetics of HOO, CH3OO, and O2•− Scavenging by Quercetin and Flavonoid Catecholic Metabolites
by Ana Amić and Denisa Mastiľák Cagardová
Antioxidants 2023, 12(6), 1154; https://doi.org/10.3390/antiox12061154 - 25 May 2023
Cited by 1 | Viewed by 1071
Abstract
Reaction kinetics have been theoretically examined to ascertain the potency of quercetin (Q) and flavonoid catecholic metabolites 15 in the inactivation of HOO, CH3OO, and O2•− under physiological conditions. In lipidic [...] Read more.
Reaction kinetics have been theoretically examined to ascertain the potency of quercetin (Q) and flavonoid catecholic metabolites 15 in the inactivation of HOO, CH3OO, and O2•− under physiological conditions. In lipidic media, the koverallTST/Eck rate constants for the proton-coupled electron transfer (PCET) mechanism indicate the catecholic moiety of Q and 15 as the most important in HOO and CH3OO scavenging. 5-(3,4-Dihydroxyphenyl)-γ-valerolactone (1) and alphitonin (5) are the most potent scavengers of HOO and CH3OO, respectively. The koverallMf rate constants, representing actual behavior in aqueous media, reveal Q as more potent in the inactivation of HOO and CH3OO via single electron transfer (SET). SET from 3-O phenoxide anion of Q, a structural motif absent in 15, represents the most contributing reaction path to overall activity. All studied polyphenolics have a potency of O2•− inactivation via a concerted two-proton–coupled electron transfer (2PCET) mechanism. The obtained results indicate that metabolites with notable radical scavenging potency, and more bioavailability than ingested flavonoids, may contribute to human health-promoting effects ascribed to parent molecules. Full article
(This article belongs to the Special Issue Theoretical and Computational Chemistry in Antioxidant Research)
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