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Molecules 2012, 17(7), 7645-7665; doi:10.3390/molecules17077645
Article

Butylated Hydroxytoluene Analogs: Synthesis and Evaluation of Their Multipotent Antioxidant Activities

1, 1, 1, 1, 1,2 and 1,*
1 Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Malaysia 2 Chemistry Department, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia
* Author to whom correspondence should be addressed.
Received: 9 April 2012 / Revised: 1 June 2012 / Accepted: 12 June 2012 / Published: 25 June 2012
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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.
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 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
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Yehye, W.A.; Abdul Rahman, N.; A. Alhadi, A.; Khaledi, H.; Ng, S.W.; Ariffin, A. Butylated Hydroxytoluene Analogs: Synthesis and Evaluation of Their Multipotent Antioxidant Activities. Molecules 2012, 17, 7645-7665.

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