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(Received for publication, September 6, 1996, and in revised form, October 30, 1996)
From the Department of Biochemistry and Molecular Biology,
University of Kansas Medical Center,
Kansas City, Kansas 66160-7421
Nonenzymatic protein glycation (Maillard
reaction) leads to heterogeneous, toxic, and antigenic advanced
glycation end products ("AGEs") and reactive precursors that have
been implicated in the pathogenesis of diabetes, Alzheimer's disease,
and normal aging. In vitro inhibition studies of AGE
formation in the presence of high sugar concentrations are difficult to
interpret, since AGE-forming intermediates may oxidatively arise from
free sugar or from Schiff base condensation products with protein amino
groups, rather than from just their classical Amadori rearrangement
products. We recently succeeded in isolating an Amadori intermediate in the reaction of ribonuclease A (RNase) with ribose (Khalifah, R. G.,
Todd, P., Booth, A. A., Yang, S. X., Mott, J. D., and Hudson, B. G. (1996) Biochemistry 35, 4645-4654) for rapid studies of post-Amadori AGE formation in absence of free sugar or reversibly formed Schiff base precursors to Amadori products. This provides a new
strategy for a better understanding of the mechanism of AGE inhibition
by established inhibitors, such as aminoguanidine, and for searching
for novel inhibitors specifically acting on post-Amadori pathways of
AGE formation. Aminoguanidine shows little inhibition of post-Amadori
AGE formation in RNase and bovine serum albumin, in contrast to its
apparently effective inhibition of initial (although not late) stages
of glycation in the presence of high concentrations of sugar. Of
several derivatives of vitamins B1 and B6
recently studied for possible AGE inhibition in the presence of glucose
(Booth, A. A., Khalifah, R. G., and Hudson, B. G. (1996) Biochem.
Biophys. Res. Commun. 220, 113-119), pyridoxamine and, to a
lesser extent, thiamine pyrophosphate proved to be novel and effective
post-Amadori inhibitors that decrease the final levels of AGEs formed.
Our mechanism-based approach to the study of AGE inhibition appears
promising for the design and discovery of novel post-Amadori AGE
inhibitors of therapeutic potential that may complement others, such as
aminoguanidine, known to either prevent initial sugar attachment or to
scavenge highly reactive dicarbonyl intermediates.
Volume 272, Number 9,
Issue of February 28, 1997
pp. 5430-5437
©1997 by The American Society for Biochemistry and Molecular Biology, Inc.
NOVEL INHIBITION OF POST-AMADORI GLYCATION PATHWAYS
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