Antioxidant properties of argpyrimidine.
Argpyrimidine, the product of non-enzymatic protein glycation by methylglyoxal, has been implicated in the pathophysiology of diabetes mellitus and neurodegenerative diseases. Chemically, argpyrimidine is a substituted pyrimidinol with structural features common to known antioxidants. The objective of this study was to investigate the antioxidant properties of argpyrimidine. Argpyrimidine was synthesized by mixing L-arginine with 3-acetoxypentane-2,4-dione under acidic conditions and purified by chromatography. Argpyrimidine inhibited lipid peroxidation of rat brain homogenates catalyzed by hydroxyl radicals, metal ions, and autooxidation in a concentration- and time-dependent manner. In addition, argpyrimidine scavenged superoxide anion, 1,1-diphenyl 2-picryl-hydrazyl-stable free radical, intracellular-hydrogen peroxide, and inhibited free-radical-mediated nicking of plasmid-DNA. Taken together, our data suggest that argpyrimidine has antioxidant properties and may therefore have biological relevance in pathophysiologies associated with diabetes mellitus and neurodegenerative diseases.
Sreejayan
Nair
N
Division of Pharmaceutical Sciences, School of Pharmacy, College of Health Sciences and Center for Cardiovascular Research and Alternative Medicine, University of Wyoming, Laramie, WY 82071, USA. sreejay@uwyo.edu
Yang
Xiaoping
X
Palanichamy
Kamalakannan
K
Dolence
Kurt
K
Ren
Jun
J
D000975:Antioxidants; D001205:Ascorbic Acid / Q000037:antagonists & inhibitors / Q000494:pharmacology; D001713:Biphenyl Compounds; D045744:Cell Line, Tumor; D004247:DNA / Q000187:drug effects; D005290:Ferric Compounds / Q000737:chemistry; D005296:Ferrous Compounds / Q000737:chemistry; D016166:Free Radical Scavengers; D006801:Humans; D006861:Hydrogen Peroxide / Q000037:antagonists & inhibitors / Q000494:pharmacology; D020287:In Situ Nick-End Labeling; D015227:Lipid Peroxidation / Q000187:drug effects; D009952:Ornithine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D016877:Oxidants / Q000494:pharmacology; D010084:Oxidation-Reduction; D018384:Oxidative Stress / Q000187:drug effects; D010851:Picrates / Q000737:chemistry; D010957:Plasmids / Q000235:genetics; D011743:Pyrimidines / Q000138:chemical synthesis / Q000494:pharmacology*; D013481:Superoxides / Q000378:metabolism
D000975:Antioxidants; D001713:Biphenyl Compounds; D005290:Ferric Compounds; D005296:Ferrous Compounds; D016166:Free Radical Scavengers; D016877:Oxidants; D010851:Picrates; D011743:Pyrimidines; C107313:argpyrimidine; D013481:Superoxides; D004247:DNA; D006861:Hydrogen Peroxide; C004931:1,1-diphenyl-2-picrylhydrazyl; D009952:Ornithine; D001205:Ascorbic Acid