19005-57-3Relevant articles and documents
Reaction of malondialdehyde-DNA adducts with hydrazines - Development of a facile assay for quantification of malondialdehyde equivalents in DNA
Otteneder, Michael,Plastaras, John P.,Marnett, Lawrence J.
, p. 312 - 318 (2002)
Malondialdehyde is a ubiquitous product of lipid peroxidation that reacts with DNA to form premutagenic lesions. Principal among them is pyrimido-[1,2-α]purin-10(3H)-one (M1G). M1G has recently been found to be a reactive electrophile in DNA that couples with amines at basic pH or hydroxylamines at neutral pH. We explored the reaction of M1G with hydrazines because of the possibility that the latter could act as bifunctional nucleophiles to strip the malondialdehyde equivalent from DNA. Pentafluorophenylhydrazine reacted rapidly with M1G to form a hydrazone conjugate. This hydrazone was stable at room temperature and did not cyclize to form the corresponding pyrazole. In contrast, phenylhydrazine and benzylhydrazine reacted with M1G to form phenylpyrazole and benzylpyrazole, respectively. Pentafluorobenzylhydrazine reacted rapidly with M1G to form pentafluorobenzylpyrazole and dG in near quantitative yield. This reaction formed the basis for a quantitative assay for the presence of M1G or M1G equivalents in DNA or protein that utilized gas chromatography/negative chemical ionization mass spectrometry. The assay was extended to the oxopropenyl donors, M1A, base propenal, and Nε-3-oxopropenyl-lysine. Analysis of DNA treated with bleomycin demonstrated a linear increase in the level of oxopropenyl groups that plateaued at approximately 1 oxopropenyl group/100 bases at a bleomycin concentration of 200 μM. Parallel analysis of M1G in the samples revealed that this adduct represents a small fraction of the total oxopropenyl units generated in DNA by treatment with bleomycin.
A rapid, sensitive and solvent-less method for determination of malonaldehyde in meat by stir bar sorptive extraction coupled thermal desorption and gas chromatography/mass spectrometry with in situ derivatization
Ruan, Eric Dongliang,Aalhus, Jennifer,Juárez, Manuel
, p. 2723 - 2728 (2014)
RATIONALE The traditional methods for analysis of malonaldehyde (MDA), such as the thiobarbituric acid (TBA) assay, require strong acidity at high temperature for derivatization and lack specificity in analysis. Stir bar sorptive extraction (SBSE) coupled with thermal desorption-gas chromatography/mass spectrometry (TD-GC/MS) with in situ derivatization using pentafluorophenylhydrazine (PFPH) under mild conditions is an emerging technique for MDA analysis. METHODS MDA in meat was derivatized with PFPH at pH ~4 for 1 h at room temperature, forming a relative stable derivative of MDA-PFPH. The derivative of MDA-PFPH was simultaneously extracted using SBSE. Then, MDA-PFPH was thermally released and quantitatively analyzed by GC/MS in selected ion monitoring (SIM) mode. RESULTS The method of SBSE-TD-GC/MS for MDA analysis with in situ derivatization was optimized and validated with good linearity, specificity and limit of detection/quantification (LOD/LOQ). The method was successfully applied for analysis of MDA in raw and cooked meat (pork). CONCLUSIONS The SBSE-TD-GC/MS method was suitable to monitor and analyze MDA in meat samples at trace levels. The simple, sensitive and solvent-less method with moderated in situ derivatization can be applied for analysis of MDA in a wide variety of foods and biological samples.
