Scientific Article
previous document  unige:10533  next document
add to browser collection

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

Ancerewicz, J.
Migliavacca, E.
Testa, Bernard
Bree, F.
Zini, R.
Tillement, J. P.
Labidalle, S.
show hidden authors show all authors [1 - 12]
Published in Free radical biology & medicine. 1998, vol. 25, no. 1, p. 113-120
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/*chemistryBepridil/analogs & derivatives/metabolismBiphenyl CompoundsComputer SimulationCresols/chemistryFree Radical Scavengers/chemistryFree Radicals/metabolismHydroquinones/chemistryModels, ChemicalPhenols/chemistryPicratesStructure-Activity RelationshipTrimetazidine/*analogs & derivatives/*chemistryVitamin E/chemistry
PMID: 9655529
Full text
(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

542 hits

0 download


Deposited on : 2010-08-06

Export document
Format :
Citation style :