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Butylated Hydroxytoluene Analogs: Synthesis and Evaluation of Their Multipotent Antioxidant Activities
Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Malaysia
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; in revised form: 1 June 2012 / Accepted: 12 June 2012 / Published: 25 June 2012
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
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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.
Yehye WA, Abdul Rahman N, A. Alhadi A, Khaledi H, Ng SW, Ariffin A. Butylated Hydroxytoluene Analogs: Synthesis and Evaluation of Their Multipotent Antioxidant Activities. Molecules. 2012; 17(7):7645-7665.
Yehye, Wageeh A.; Abdul Rahman, Noorsaadah; A. Alhadi, Abeer; Khaledi, Hamid; Ng, Seik Weng; Ariffin, Azhar. 2012. "Butylated Hydroxytoluene Analogs: Synthesis and Evaluation of Their Multipotent Antioxidant Activities." Molecules 17, no. 7: 7645-7665.