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Butylated Hydroxytoluene Analogs: Synthesis and Evaluation of Their Multipotent Antioxidant Activities
Molecules (2012)
  • Azhar Ariffin, University of Malaya
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.
  • 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
Publication Date
Citation Information
Azhar Ariffin. "Butylated Hydroxytoluene Analogs: Synthesis and Evaluation of Their Multipotent Antioxidant Activities" Molecules Vol. 17 Iss. 7 (2012)
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