Enhanced antioxidant activity in Imidazolium-based protic organic salts: An insight into structure activity relationship via experimental and modelling approaches
[Display omitted] •Four imidazolium ([1MeimPS]+) based protic ionic liquids (PILs) are developed with potential amine-based structural functionalities.•All the reported PILs have shown excellent antioxidant potential depicting antiaging properties.•Glutamine based-IL ([1MeimPS][Gln]) showed selectiv...
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Veröffentlicht in: | Journal of molecular liquids 2024-06, Vol.404, p.124964, Article 124964 |
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•Four imidazolium ([1MeimPS]+) based protic ionic liquids (PILs) are developed with potential amine-based structural functionalities.•All the reported PILs have shown excellent antioxidant potential depicting antiaging properties.•Glutamine based-IL ([1MeimPS][Gln]) showed selectively promising antioxidant activity.•Least IC50 values are observed for Glutamine based-PIL ([1MeimPS][Gln]) indicating maximum antioxidant activity.•Maximum IC50 values are observed for Proline based-PIL ([1MeimPS][Pro]) indicating least antioxidant activity.•Increased primary amine moieties enhanced the antioxidant activity by providing more radical scavenging sites.
Sulfonyl hydroxide functionalized imidazolium based protic ionic liquids (PILs) have been evaluated as a new form of antioxidants. The antioxidant activity was performed using free radical quenching using UV–visible spectroscopy and cyclic voltammetry. The studies confirmed that the investigated ILs with variable anions exhibited substantial radical scavenging activity. In UV–Visible study, Glutamine based-IL ([1MeimPS][Gln]) showed least IC50 value of 95 µM indicating maximum radical quenching activity as an oxidant, while proline based-IL ([1MeimPS]Pro]) exhibited highest IC50 value of 675 µM, demonstrating least anti-oxidant activity. Moreover, cyclic voltammetry results complemented well the UV–visible findings with least IC50 value of 90 µM for [1MeimPS][Gln], showing maximum antioxidant activity, and highest IC50 value of 593 µM for [1MeimPS]Pro], exhibiting the least antioxidant activity. The presence of two primary amines moieties in glutaminate anion may be responsible for enhanced antioxidant activity by providing more active sites for radical quenching. Contrarily, lack of primary amine functionality in prolinate anion may contribute to reduced antioxidant activity of respective IL. The Density Functional Theory (DFT) calculations predicted that the trend of radical scavenging potential was comparable with the experimentally obtained IC50 values. Molecular Electrostatic Potential (MESP) Maps illustrated that [1MeimPS][Pro] has the maximum red zones indicating a poor potential against electron scavenging capacity among all the studied ILs, while blue region in [1MeimPS][Gln], corresponding to low electron density, suggested strong attraction for the incoming electrons. Also, the high electronic distribution of HOMO orbital, appreciable stability, and significant chemical potential to atta |
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ISSN: | 0167-7322 1873-3166 |
DOI: | 10.1016/j.molliq.2024.124964 |