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J. Biol. Chem., Vol. 277, Issue 5, 3397-3403, February 1, 2002
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From the Reactive carbonyl compounds are formed
during autoxidation of carbohydrates and peroxidation of lipids. These
compounds are intermediates in the formation of advanced glycation end
products (AGE) and advanced lipoxidation end products (ALE) in tissue
proteins during aging and in chronic disease. We studied the
reaction of carbonyl compounds glyoxal (GO) and
glycolaldehyde (GLA) with pyridoxamine (PM), a potent post-Amadori
inhibitor of AGE formation in vitro and of development of
renal and retinal pathology in diabetic animals. PM reacted rapidly
with GO and GLA in neutral, aqueous buffer, forming a Schiff base
intermediate that cyclized to a hemiaminal adduct by intramolecular
reaction with the phenolic hydroxyl group of PM. This bicyclic
intermediate dimerized to form a five-ring compound with a central
piperazine ring, which was characterized by electrospray
ionization-liquid chromatography/mass spectrometry, NMR, and x-ray
crystallography. PM also inhibited the modification of lysine
residues and loss of enzymatic activity of RNase in the presence of GO
and GLA and inhibited formation of the AGE/ALE
N
A Post-Amadori Inhibitor Pyridoxamine Also Inhibits Chemical
Modification of Proteins by Scavenging Carbonyl Intermediates of
Carbohydrate and Lipid Degradation*
§,
Department of Biochemistry and Molecular
Biology, University of Kansas Medical Center, Kansas City, Kansas
66160 and the ¶ Department of Chemistry and Biochemistry,
University of South Carolina, Columbia, South Carolina 29208
-(carboxymethyl)lysine during reaction of
GO and GLA with bovine serum albumin. Our data suggest that the AGE/ALE
inhibitory activity and the therapeutic effects of PM observed in
diabetic animal models depend, at least in part, on its ability to trap
reactive carbonyl intermediates in AGE/ALE formation, thereby
inhibiting the chemical modification of tissue proteins.
*
This work was supported by National Institute of
Diabetes and Digestive and Kidney Diseases Research Grants 5R37
DK18381-28 (to B. G. H.) and DK-19971 (to J. W. B.) and by a
research grant from BioStratum, Inc. (to P. A. V.).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.
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