Influence of the microenvironment of thiol groups in low molecular mass thiols and serum albumin on the reaction with methylglyoxal

Chemico-biological Interactions
Jelena M AćimovićLjuba M Mandić

Abstract

Methylglyoxal (MG), a reactive alpha-oxoaldehyde that is produced in higher quantities in diabetes, uremia, oxidative stress, aging and inflammation, reacts with the thiol groups (in addition to the amino and guanidino groups) of proteins. This causes protein modification, formation of advanced glycated end products (AGEs) and cross-linking. Low molecular mass thiols can be used as competitive targets for MG, preventing the reactions mentioned above. Therefore, this paper investigated how the microenvironment of the thiol group in low molecular mass thiols (cysteine, N-acetylcysteine (NAcCys), carboxymethylcysteine (CMC) and glutathione (GSH)) and human serum albumin (HSA) affected the thiol reaction with MG. The SH group reaction course was monitored by (1)H-NMR spectroscopy and spectrophotometric quantification. Changes in the HSA molecules were monitored by SDS-PAGE. The microenvironment of the SH group had a major effect on its reactivity and on the product yield. The reactivity of SH groups decreased in the order Cys>GSH>NAcCys. CMC did not react. The percentages of the reacted SH groups in the equilibrium state were almost equal, regardless of the ratio of thiol compound/MG (1:1, 1:2, 1:5): 38.1 + or - 0.9%; 38.2 + or - 0...Continue Reading

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Citations

Jul 11, 2012·International Journal of Cell Biology·Pamela Boon Li Pun, Michael P Murphy
Apr 16, 2013·Analytical Biochemistry·Vesna B JovanovićLjuba M Mandić
Jan 24, 2015·Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences·Kamila BorowczykRafał Głowacki
Sep 2, 2015·Metallomics : Integrated Biometal Science·Ana Z PenezićLjuba M Mandić

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