Identification of DNA adducts of methylglyoxal

Journal article

Publication Details

Author(s): Frischmann M, Bidmon C, Angerer J, Pischetsrieder M
Journal: Chemical Research in Toxicology
Publisher: American Chemical Society
Publication year: 2005
Volume: 18
Pages range: 1586-1592
ISSN: 0893-228X


Methylglyoxal (MG) is a sugar degradation product, which is endogenously formed by fragmentation of triose phosphates during glycolysis, ketone body metabolism of acetone, and catabolism of threonine. Food, beverages, and medical products are important exogenous sources with concentrations of up to 100 μM MG. MG is a reactive dicarbonyl compound, which easily modifies amino groups of proteins (glycation reaction) and thereby induces proinflammatory responses. Moreover, increased mutation frequencies in mammalian cells after treatment with MG have been reported, which are caused by stable modifications of DNA bases. Thus far, two types of adducts have been identified, which are formed during the reaction of free guanine or 2′-deoxyguanosine with high MG concentrations. In this study, we investigated the prolonged exposure of DNA to physiological MG concentrations. DNA was incubated with MG, enzymatically hydrolyzed to release the free nucleosides, and then analyzed by LC-MS/MS. We detected four products, which were derived from the reaction of 2′-deoxyguanosine and 2′-deoxyadenosine with 1 and 2 equiv of MG each. The adducts with 1 equiv of MG were identified as N2-(1- carboxyethyl)-2′-deoxyguanosine (CEdG) and N6-(1-carboxyethyl)- 2′-deoxyadenosine. LC-MS/MS was optimized for these compounds, and incubation of DNA was repeated using physiological concentrations of 10 μM MG. Thereby, CEdG proved to be the most sensitive and suitable marker for the reaction of DNA with MG (negative MRM mode, three mass transitions [M - 1] - 338→178, 338→106, and 338→149). © 2005 American Chemical Society.

FAU Authors / FAU Editors

Angerer, Jürgen apl. Prof. Dr.
Medizinische Fakultät
Pischetsrieder, Monika Prof. Dr.
Lehrstuhl für Lebensmittelchemie (Henriette-Schmidt-Burkhardt Lehrstuhl)

Additional Organisation
Emil-Fischer-Zentrum (Emil Fischer Center)

How to cite

Frischmann, M., Bidmon, C., Angerer, J., & Pischetsrieder, M. (2005). Identification of DNA adducts of methylglyoxal. Chemical Research in Toxicology, 18, 1586-1592.

Frischmann, Matthias, et al. "Identification of DNA adducts of methylglyoxal." Chemical Research in Toxicology 18 (2005): 1586-1592.


Last updated on 2018-19-04 at 02:40