structural modification of DNA nucleosides by nonenzymatic glycation: an in vitro study based on the reactions of glyoxal and methylglyoxal with 2'-deoxyguanosine

Methylglyoxal and glyoxal are generated from the oxidation of carbohydrates and lipids, and like d-glucose have been shown to nonenzymatically react with proteins to form advanced glycation end products (AGEs). AGEs can occur both in vitro and in vivo, and these compounds have been shown to exacerba...

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Bibliographic Details
Published in:Analytical and bioanalytical chemistry 2008, Vol.390 (2), p.679-688
Main Authors: Li, Yuyuan, Cohenford, Menashi A, Dutta, Udayan, Dain, Joel A
Format: Article
Language:English
Subjects:
2'-Deoxyguanosine
Advanced glycation end products
Analytical Chemistry
Biochemistry
Characterization and Evaluation of Materials
Chemistry
Chemistry and Materials Science
Chromatography, High Pressure Liquid
Deoxyguanosine - chemistry
DNA - chemistry
Enzymes - metabolism
Food Science
Glycosylation
Glyoxal
Glyoxal - chemistry
Hydrogen-Ion Concentration
Laboratory Medicine
Maillard reaction products
Methylation
Methylglyoxal
Molecular Structure
Monitoring/Environmental Analysis
Nucleosides - chemical synthesis
Nucleosides - chemistry
Original Paper
Spectrometry, Mass, Electrospray Ionization
Spectrophotometry
Temperature
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Summary:Methylglyoxal and glyoxal are generated from the oxidation of carbohydrates and lipids, and like d-glucose have been shown to nonenzymatically react with proteins to form advanced glycation end products (AGEs). AGEs can occur both in vitro and in vivo, and these compounds have been shown to exacerbate many of the long-term complications of diabetes. Earlier studies in our laboratory reported d-glucose, d-galactose, and d/l-glyceraldehyde formed AGEs with nucleosides. The objective of this study was to focus on purines and pyrimidines and to analyze these DNA nucleoside derived AGE adducts with glyoxal or methylglyoxal using a combination of analytical techniques. Studies using UV and fluorescence spectroscopy along with mass spectrometry provided for a thorough analysis of the nucleoside AGEs and demonstrated that methylglyoxal and glyoxal reacted with 2'-deoxyguanosine via the classic Amadori pathway, and did not react appreciably with 2'-deoxyadenosine, 2'-deoxythymidine, and 2'-deoxycytidine. Additional findings revealed that methylglyoxal was more reactive than glyoxal.
ISSN:1618-2642
1618-2650
DOI:10.1007/s00216-007-1682-4