Document Detail


Efficient scavenging of hydroxyl radicals and inhibition of lipid peroxidation by novel analogues of 1,3,7-trimethyluric acid.
MedLine Citation:
PMID:  11798008     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
New water-soluble analogues of 1,3,7-trimethyluric acid with N-1 methyl replaced by various groups were prepared and evaluated for their ability to scavenge hydroxyl radicals as well as their protective potential against lipid peroxidation in erythrocyte membranes. The deoxyribose degradation method indicates that all the analogues tested effectively scavenge hydroxyl radicals and some of them show better activity than uric acid and methyluric acids. These effects are shown to be concentration dependent and are more potent at low concentrations (10-50 microM). Among the analogues tested, 1-butenyl-, 1-propargyl- and 1-benzyl-3,7-dimethyluric acids show high hydroxyl radical scavenging property with a reaction rate constant (Ks) of 3.2-6.7 x 10(10) M(-1) S(-1), 2.3-3.7 x 10(10) M(-1) S(-1) and 2.4-3.7 x 10(10) M(-1) S(-1), respectively. The effectiveness of these analogues as hydroxyl radical scavengers appears to be better than mannitol (Ks, 1.9-2.5 x 10(9) M(-1) S(-1)). With the exception of 1-pentyl- and 1-(2'-oxopropyl)-3,7-dimethyluric acids, all other analogues tested are effective inhibitors of tert-butylhydroperoxide-induced lipid peroxidation in human erythrocyte membranes. All the analogues tested are susceptible to peroxidation in the presence of hemoprotein and hydrogen peroxide. The present study has pointed out that it is possible to significantly enhance the antioxidant property of 1,3,7-trimethyluric acid by structural modification at N-1 position. Such compounds may be useful as antioxidants in vivo.
Authors:
V B Bhat; G R Sridhar; K M Madyastha
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Life sciences     Volume:  70     ISSN:  0024-3205     ISO Abbreviation:  Life Sci.     Publication Date:  2001 Dec 
Date Detail:
Created Date:  2002-01-18     Completed Date:  2002-01-30     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0375521     Medline TA:  Life Sci     Country:  England    
Other Details:
Languages:  eng     Pagination:  381-93     Citation Subset:  IM    
Affiliation:
Department of Organic Chemistry, Indian Institute of Science, Bangalore.
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MeSH Terms
Descriptor/Qualifier:
Dose-Response Relationship, Drug
Erythrocyte Membrane / drug effects,  metabolism*
Free Radical Scavengers / metabolism*
Humans
Hydroxyl Radical / metabolism*
Lipid Peroxidation / drug effects*
Oxidants / metabolism*
Uric Acid / analogs & derivatives*,  pharmacology*
Chemical
Reg. No./Substance:
0/Free Radical Scavengers; 0/Oxidants; 3352-57-6/Hydroxyl Radical; 5415-44-1/1,3,7-trimethyluric acid; 69-93-2/Uric Acid

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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