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Originally published In Press as doi:10.1074/jbc.M003263200 on May 8, 2000

J. Biol. Chem., Vol. 275, Issue 28, 21177-21184, July 14, 2000
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Pyridoxamine, an Inhibitor of Advanced Glycation Reactions, Also Inhibits Advanced Lipoxidation Reactions
MECHANISM OF ACTION OF PYRIDOXAMINE*

Joelle M. OnoratoDagger , Alicia J. Jenkins§, Suzanne R. ThorpeDagger , and John W. BaynesDagger

From the Dagger  Department of Chemistry and Biochemistry, University of South Carolina, Columbia, South Carolina 29208 and the § Department of Medicine, Medical University of South Carolina, Charleston, South Carolina 29425

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 we 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) Nepsilon -(carboxymethyl)lysine, Nepsilon -(carboxyethyl)lysine, malondialdehyde-lysine, and 4-hydroxynonenal-lysine. PM also inhibited lysine modification and formation of ALEs during copper-catalyzed oxidation of low density lipoprotein. 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.

* This work was supported by NIDDKD Research Grant DK-19971 from the National Institutes of Health.The costs of publication of this article were defrayed in part by the payment of page charges. The article must therefore be hereby marked "advertisement" in accordance with 18 U.S.C. Section 1734 solely to indicate this fact.

To whom all correspondence should be addressed: Dept. of Chemistry and Biochemistry, University of South Carolina, Columbia SC 29208. Tel.: 803-777-7272; Fax: 803-777-7272; E-mail: baynes@mail.chem.sc.edu.

Copyright © 2000 by The American Society for Biochemistry and Molecular Biology, Inc.
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