Jan 18, 2007

Chemical nature of stochastic generation of protein-based carbonyls: metal-catalyzed oxidation versus modification by products of lipid oxidation

Chemical Research in Toxicology
Quan YuanLawrence M Sayre


An assessment of 2,4-dinitrophenylhydrazine (DNPH)-detectable protein-based carbonyls is one of the most common assays used to quantify oxidative stress in vitro and in vivo. In this study, we compared, for the lipid-binding protein beta-lactoglobulin, the extent to which carbonyl reactivity could be introduced by adventitious metal-catalyzed oxidation (MCO) in the absence and presence of a polyunsaturated lipid or by treatment with various individual bifunctional lipid oxidation products capable of introducing carbonyls into proteins by adduction to nucleophilic side chains. With metal ions and either O2/reductant or H2O2 as the terminal oxidant, the maximal level of DNPH-detectable carbonyl generation obtainable in several hours was 0.1-0.2 mol carbonyl per mol protein monomer, with Cu(II) being more effective than Fe(II). Exposure instead to bifunctional lipoxidation-derived aldehydes (1-2 mM) generated in some cases in excess of 1 mol carbonyl per mol protein. The rank order of carbonyl incorporation reactivity was acrolein > 4-oxo-2-nonenal > 4-hydroxy-2-nonenal > 2,4-decadienal > malondialdehyde. Protein cross-linking ability followed a somewhat different rank order. Parallel studies on reductively methylated beta-lactogl...Continue Reading

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Mentioned in this Paper

Stochastic Processes
Peptide Mapping
Hydrogen Peroxide
Beta Lactoglobulin
Oxidative Stress

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