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Scientific article
English

Structure-property relationships of trimetazidine derivatives and model compounds as potential antioxidants

Published inFree radical biology & medicine, vol. 25, no. 1, p. 113-120
Publication date1998
Abstract

Twenty-five compounds (trimetazidine derivatives and other compounds, mostly having a free phenolic group) were examined for their radical scavenging and antioxidant properties. Their reaction with DPPH (2,2-diphenyl-1-picrylhydrazyl) as a measure of radical scavenging capacity was assessed by two parameters, namely EC50 (the concentration of antioxidant decreasing DPPH by 50%), and log Z, a kinetic parameter proposed here and derived from initial second-order rate constants and antioxidant/DPPH ratios. Antioxidant activities were determined by the inhibition of lipid peroxidation and albumin oxidation. The most active compounds were derivatives having a trolox or hydroquinone moiety. Physicochemical and structural properties were determined by molecular modeling as lipophilicity (virtual log P calculations) and H-Surf (solvent-accessible surface of hydroxyl hydrogen) and by quantum mechanical calculations (deltaH(ox) = oxidation enthalpy; deltaH(abs) = enthalpy of hydrogen abstraction). QSAR models were derived to identify molecular mechanisms responsible for the reactivity toward the DPPH radical and for the inhibition of lipid peroxidation. A useful prediction of antioxidant capacity could be achieved from calculated molecular properties and the kinetic parameter developed here.

Keywords
  • Antioxidants/*chemistry
  • Bepridil/analogs & derivatives/metabolism
  • Biphenyl Compounds
  • Computer Simulation
  • Cresols/chemistry
  • Free Radical Scavengers/chemistry
  • Free Radicals/metabolism
  • Hydroquinones/chemistry
  • Models, Chemical
  • Phenols/chemistry
  • Picrates
  • Structure-Activity Relationship
  • Trimetazidine/*analogs & derivatives/*chemistry
  • Vitamin E/chemistry
Affiliation Not a UNIGE publication
Citation (ISO format)
ANCEREWICZ, J. et al. Structure-property relationships of trimetazidine derivatives and model compounds as potential antioxidants. In: Free radical biology & medicine, 1998, vol. 25, n° 1, p. 113–120. doi: 10.1016/s0891-5849(98)00072-0
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ISSN of the journal0891-5849
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