Radical Scavenging and Endogenous Defence System Inducing Activities of 5-[(4-Chlorophenoxy)methyl]-1,3,4-oxadiazole-2-thiol: A Novel Antioxidant

Author(s): N. Shehzadi1*, K. Hussain, M. T. Khan1, N. I. Bukhari, M. Islam, M. Salman, S. Qamar, A. A. Iqbal, S. Z. Siddiqui2, A. Rehman2 and M. A. Abbasi2
Punjab University College of Pharmacy, University of the Punjab, Allama Iqbal Campus, Lahore-54000, 1The University of Lahore, 1-Km, Defence Road (Off Raiwind Road), Bhobatian Chowk, 2Department of Chemistry, Government College University, Lahore-54000, Pakistan

Correspondence Address:
The University of Lahore, 1-Km, Defence Road (Off Raiwind Road), Bhobatian Chowk, Lahore-54000, Pakistan, E-mail: [email protected]; [email protected]

5-[(4-Chlorophenoxy)methyl]-1,3,4-oxadiazole-2-thiol owing to the presence of –SH group is expected to have a significant reducing potential, which could be translated into antioxidant activity and to prove this, the present study explored the antioxidant potential and binding pattern of this compound to oxidative stress-related protein targets. The antioxidant properties were determined using in vitro methods with ascorbic acid and butylated hydroxytoluene as standards while interactions of 5-[(4-chlorophenoxy)methyl]-1,3,4-oxadiazole-2-thiol with protein tyrosine kinase 2-β and glutathione reductase were determined using online software, Mcule 1-Click Docking, 3DLigandSite and COACH. The antioxidant activity of 5-[(4-chlorophenoxy)methyl]-1,3,4-oxadiazole-2-thiol was found to be 89.30±0.013, 81.20±0.002, 80.52±0.016, 54.81±0.007, 52.87±0.008, 34.44±0.019 and 19.91±0.014 % in hydrogen peroxide scavenging assay, 2,2-diphenyl-1-picrylhydrazyl radical scavenging assay, phosphomolybdenum assay, nitric oxide scavenging assay, reducing power assay, ferric thiocyanate assay and β-carotene bleaching assay, respectively. In all these assays, EC50 of 5-[(4-chlorophenoxy)methyl]-1,3,4-oxadiazole-2-thiol ranged from 0.32-0.93 mg/ml. The docking results indicated excellent binding to protein tyrosine kinase 2-β and glutathione reductase, maximum for the latter. The results of the present study revealed that 5-[(4-chlorophenoxy)methyl]-1,3,4-oxadiazole-2-thiol has the propensity to abrogate oxidation by inducing endogenous defence system and preventing radical chain reactions, hence might be considered a potential antioxidant for further investigations.

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