Structure-property relationships of trimetazidine derivatives and model compounds as potential antioxidants.
Details
Serval ID
serval:BIB_6341
Type
Article: article from journal or magazin.
Collection
Publications
Institution
Title
Structure-property relationships of trimetazidine derivatives and model compounds as potential antioxidants.
Journal
Free Radical Biology and Medicine
ISSN
0891-5849 (Print)
ISSN-L
0891-5849
Publication state
Published
Issued date
1998
Volume
25
Number
1
Pages
113-120
Language
english
Notes
Publication types: Journal Article ; Research Support, Non-U.S. Gov't
Publication Status: ppublish
Publication Status: ppublish
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, 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
OAI-PMH
Pubmed
Web of science
Create date
19/11/2007 10:30
Last modification date
20/08/2019 14:19