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Butylated Hydroxytoluene Analogs: Synthesis and Evaluation of Their <em>Multipotent </em>Antioxidant Activities

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Author(s): Wageeh A. Yehye | Noorsaadah Abdul Rahman | Abeer A. Alhadi | Hamid Khaledi | Ng Seik Weng | Azhar Ariffin

Journal: Molecules
ISSN 1420-3049

Volume: 17;
Issue: 7;
Start page: 7645;
Date: 2012;
Original page

Keywords: butylated hydroxyltolouene | drug-likeness properties | DPPH | lipid peroxidation | multipotent antioxidant | rule-of-five | PASS and activity prediction | thiosemicarbazide | 1 | 2 | 4-triazole | 1 | 3 | 4-thiadiazole

ABSTRACT
A computer-aided predictions of antioxidant activities were performed with the Prediction Activity Spectra of Substances (PASS) program. Antioxidant activity of compounds 1, 3, 4 and 5 were studied using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and lipid peroxidation assays to verify the predictions obtained by the PASS program. Compounds 3 and 5 showed more inhibition of DPPH stable free radical at 10−4 M than the well-known standard antioxidant, butylated hydroxytoluene (BHT). Compound 5 exhibited promising in vitro inhibition of Fe2+-induced lipid peroxidation of the essential egg yolk as a lipid-rich medium (83.99%, IC50 16.07 ± 3.51 µM/mL) compared to a-tocopherol (a-TOH, 84.6%, IC50 5.6 ± 1.09 µM/mL). The parameters for drug-likeness of these BHT analogues were also evaluated according to the Lipinski’s “rule-of-five” (RO5). All the BHT analogues were found to violate one of the Lipinski’s parameters (LogP > 5), even though they have been found to be soluble in protic solvents. The predictive polar surface area (PSA) and absorption percent (% ABS) data allow us to conclude that they could have a good capacity for penetrating cell membranes. Therefore, one can propose these new multipotent antioxidants (MPAOs) as potential antioxidants for tackling oxidative stress and lipid peroxidation processes.
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