Strategic design, theoretical insights, synthesis, and unveiling antioxidant potential in a novel ascorbic acid analog.
Antioxidant activity
Ascorbic acid
DFT calculations
Rate constants
Journal
Journal of molecular modeling
ISSN: 0948-5023
Titre abrégé: J Mol Model
Pays: Germany
ID NLM: 9806569
Informations de publication
Date de publication:
19 Apr 2024
19 Apr 2024
Historique:
received:
24
03
2024
accepted:
13
04
2024
medline:
19
4
2024
pubmed:
19
4
2024
entrez:
19
4
2024
Statut:
epublish
Résumé
In this study, we investigated the antioxidant potential of a novel ascorbic acid analog, DsD, assessing its interactions with the methylperoxyl (CH3OO·) radical in aqueous and lipid environments. Our focus was on understanding the acid-base equilibrium and how pH affects DsD's primary reaction mechanisms. Our findings indicate a marked preference for hydrogen atom transfer in lipid media, contrasting with sequential proton loss electron transfer (SPLET) in aqueous solutions. Remarkably, DsD's radical scavenging activity significantly outperforms ascorbic acid, being 4.05 and 9469.70 times more potent in polar and lipid contexts, respectively. This suggests DsD's superior efficacy as an antioxidant, potentially offering enhanced protection in biological systems. Additionally, we have demonstrated DsD's synthetic feasibility through a straightforward condensation reaction between ascorbic acid and 1,2-diaminoethane, followed by comprehensive physicochemical and spectroscopic characterization. All computational analyses in this study were conducted using the Gaussian 09 software suite, employing the M05-2X functional and the 6-31 + G(d) basis set. Enthalpy calculations were executed under standard conditions (298.15 K and 1 atm), incorporating appropriate thermodynamic corrections. Rate constants were evaluated using transition state theory (TST), and the overall assessment of radical scavenging activity was guided by the Quantum Mechanics-based Test for Overall Radical Scavenging Activity (QMORSA) protocol.
Identifiants
pubmed: 38639786
doi: 10.1007/s00894-024-05942-z
pii: 10.1007/s00894-024-05942-z
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
141Informations de copyright
© 2024. The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature.
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