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

Détails

ID Serval
serval:BIB_6341
Type
Article: article d'un périodique ou d'un magazine.
Collection
Publications
Institution
Titre
Structure-property relationships of trimetazidine derivatives and model compounds as potential antioxidants.
Périodique
Free Radical Biology and Medicine
Auteur(s)
Ancerewicz J., Migliavacca E., Carrupt P.A., Testa B., Brée F., Zini R., Tillement J.P., Labidalle S., Guyot D., Chauvet-Monges A.M., Crevat A., Le Ridant A.
ISSN
0891-5849 (Print)
ISSN-L
0891-5849
Statut éditorial
Publié
Date de publication
1998
Volume
25
Numéro
1
Pages
113-120
Langue
anglais
Notes
Publication types: Journal Article ; Research Support, Non-U.S. Gov't
Publication Status: ppublish
Résumé
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.
Mots-clé
Antioxidants/chemistry, Bepridil/analogs & derivatives, Bepridil/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, Trimetazidine/chemistry, Vitamin E/chemistry
Pubmed
Web of science
Création de la notice
19/11/2007 11:30
Dernière modification de la notice
20/08/2019 15:19
Données d'usage