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Papers In Press, published online ahead of print May 8, 2000
Department of Chemistry and Biochemistry, University of South Carolina, Columbia, SC 29208-0001
Corresponding Author: baynes{at}psc.sc.edu
Maillard or browning reactions lead to formation of advanced glycation end-products (AGEs) on protein and contribute to the increase in chemical modification of proteins during aging and in diabetes. AGE inhibitors such as aminoguanidine and pyridoxamine (PM) have proven effective in animal model and clinical studies as inhibitors of AGE formation and development of diabetic complications. We report here that PM also inhibits the chemical modification of proteins during lipid peroxidation (lipoxidation) reactions in vitro, and show that it traps reactive intermediates formed during lipid peroxidation. In reactions of arachidonate with the model protein RNase, PM prevented modification of lysine residues and formation of the advanced lipoxidation end-products (ALEs) Ne-(carboxymethyl)lysine, Ne-(carboxyethyl)lysine, malondialdehyde-lysine and 4-hydroxynonenal-lysine. PM also inhibited lysine modification and formation of ALEs during copper-catalyzed oxidation of LDL. Hexanoic acid amide and nonanedioic acid monoamide derivatives of PM were identified as major products formed during oxidation of linoleic acid in the presence of PM. We propose a mechanism for formation of these products from the 9- and 13-oxo-decadienoic acid intermediates formed during peroxidation of linoleic acid. PM, as a potent inhibitor of both AGE and ALE formation, may prove useful for limiting the increased chemical modification of tissue proteins and associated pathology in aging and chronic diseases, including both diabetes and atherosclerosis.
J. Biol. Chem, 10.1074/jbc.M003263200
Submitted on April 17, 2000
Revised on May 8, 2000
Accepted on May 8, 2000
Pyridoxamine, an inhibitor of advanced glycation reactions, also inhibits advanced lipoxidation reactions: mechanism of action of pyridoxamine
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