argpyrimidine and 1-1-diphenyl-2-picrylhydrazyl

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.

Topics: Antioxidants; Ascorbic Acid; Biphenyl Compounds; Cell Line, Tumor; DNA; Ferric Compounds; Ferrous Compounds; Free Radical Scavengers; Humans; Hydrogen Peroxide; In Situ Nick-End Labeling; Lipid Peroxidation; Ornithine; Oxidants; Oxidation-Reduction; Oxidative Stress; Picrates; Plasmids; Pyrimidines; Superoxides