Synthesis, Antioxidant, and Anti-tyrosinase Activity of Some Aromatic Oximes: An Experimental and Theoretical Study

Rafik Bensegueni; Mounia Guergouri; Chawki Bensouici; Mustapha Bencharif

doi:10.4103/jrptps.JRPTPS_46_18

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https://doi.org/10.4103/jrptps.JRPTPS_46_18

Synthesis, Antioxidant, and Anti-tyrosinase Activity of Some Aromatic Oximes: An Experimental and Theoretical Study

Author(s):

Rafik Bensegueni^{1, 2},

Mounia Guergouri²,

Chawki Bensouici³,

Mustapha Bencharif^2,*

1Université Mohamed Cherif Messaadia, Souk Ahras, Algeria

2Laboratoire de Chimie des Matériaux Constantine, Université Frères Mentouri Constantine 1, Constantine, Algeria

3Centre de Recherche en Biotechnologie, Constantine, Algeria

Journal of Reports in Pharmaceutical Sciences:Vol. 8, issue 2; 195-203

Published online:Dec 31, 2019

Article type:Research Article

How to Cite:Rafik BensegueniMounia GuergouriChawki BensouiciMustapha BencharifSynthesis, Antioxidant, and Anti-tyrosinase Activity of Some Aromatic Oximes: An Experimental and Theoretical Study.J Rep Pharm Sci.8(2):e147379.https://doi.org/10.4103/jrptps.JRPTPS_46_18.

Abstract

In this study, five oximes were synthesized, characterized, and their antioxidant activity investigated experimentally and theoretically. Labeled OX1–OX5, our oximes were subjected to three antioxidant activity assays (1,1-diphenyl-2-picrylhydrazyl, cupric reducing antioxidant capacity test [CUPRAC], and ferric reducing antioxidant power test). The related results were very fulfilling presenting certain antioxidant properties for the majority of the studied compounds, especially with CUPRAC test where OX1 and OX2 presented a better result than the used standard antioxidants. Besides, the thermodynamic molecular descriptors (bond dissociation enthalpy, ionization potential, and proton affinity) of our molecules were calculated with the density functional theory to elucidate the experimental results. The resulting values were in a good agreement with the experimental results. The second part of this work consisted of an anti-tyrosinase activity evaluation of the five oximes where three of them displayed an inhibitory effect against this enzyme. To analyze this result, a molecular docking was conducted and the obtained values were in accordance with the experience. Absorption, distribution, metabolism, and excretion properties were also assessed via Molinspiration software and all our molecules satisfied the related conditions. Thus, the conducted theoretical and experimental studies were in excellent harmony, together supporting the antioxidant power of our compounds, which could permit their use in cosmetic, pharmaceutical, or food industry domains, after further clinical tests.

Keywords

antioxidant activity

anti-tyrosinase activity

density functional theory calculations

molecular docking

oximes

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Author(s):

Rafik Bensegueni:[PubMed][Scholar]
Mounia Guergouri:[PubMed][Scholar]
Chawki Bensouici:[PubMed][Scholar]
Mustapha Bencharif:[PubMed][Scholar]