Butylated Hydroxytoluene analogs: synthesis and evaluation of their multipotent antioxidant activities

Ariffin, Azhar and Ng, S.W. and Yehye, W.A. and Rahman, N.A. and Alhadi, A.A. and Khaledi, H. (2012) Butylated Hydroxytoluene analogs: synthesis and evaluation of their multipotent antioxidant activities. Molecules, 17 (7). pp. 7645-7665. ISSN 1420-3049, DOI https://doi.org/10.3390/molecules17077645.

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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 mu M/mL) compared to alpha-tocopherol (alpha-TOH, 84.6%, IC50 5.6 +/- 1.09 mu M/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.

Item Type: Article
Additional Information: Department of Chemistry, Faculty of Science Building, University of Malaya, 50603 Kuala Lumpur, MALAYSIA
Uncontrolled Keywords: Antioxidants/*pharmacology; Biphenyl compounds/chemistry; Butylated Hydroxytoluene/*analogs & derivatives/*chemical; synthesis/chemistry/pharmacology; Crystallography; X-Ray; Cyclooxygenase inhibitors/chemistry/pharmacology; Free radical scavengers/pharmacology; Hydrogen bonding/drug effects; Inhibitory concentration 50; Lipid peroxidation/drug effects; Magnetic resonance spectroscopy; Molecular conformation; Picrates/chemistry; Stereoisomerism
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Science > Department of Chemistry
Depositing User: Miss Malisa Diana
Date Deposited: 03 Jul 2013 04:08
Last Modified: 27 Aug 2019 06:21
URI: http://eprints.um.edu.my/id/eprint/8096

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