4-oxo-2-Nonenal-d3 (Synonyms: 4ONEd3)

4-oxo-2-Nonenal-d₃ (4-ONE-d₃) contains three deuterium atoms at the terminal methyl position. It is intended for use as an internal standard for the quantification of 4-ONE by GC- or LC-mass spectrometry (MS). 4-ONE is a lipid peroxidation product derived from oxidized ω-6 polyunsaturated fatty acids such as arachidonic acid and linoleic acid.^1,2 It exhibits various biological activities such as cytotoxicity, growth inhibiting activity, genotoxicity, and chemotactic activity and has been widely used as a marker of lipid peroxidation.^1,2,3 4-ONE is a more recently identified product of lipid peroxidation.^4,5,6 It actively modifies histidine and lysine residues on proteins and causes protein cross-linking.^7,8 4-ONE also modifies 2'-deoxy guanosine, further implicating lipid peroxidation in mutagenesis and carcinogenesis.¹

1.Pryor, W.A., and Porter, N.A.Suggested mechanisms for the production of 4-hydroxy-2-nonenal from the autoxidation of polyunsaturated fatty acidsFree Radical Biology & Medicine8541-543(1990) 2.Esterbauer, H., Schaur, R.J., and Zoliner, H.Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde, and related aldehydesFree Radical Biology & Medicine1181-128(1991) 3.Sodum, R.S., and Chung, F.L.1,N2-ethenodeoxyguanosine as a potential marker for DNA adduct formation by trans-4-hydroxy-2-nonenalCancer Research48320-323(1988) 4.Rindgen, D., Nakajima, M., Wehrli, S., et al.Covalent modifications to 2'-deoxyguanosine by 4-oxo-nonenal, a novel product of lipid peroxidationChemical Research in Toxicology121195-1204(1999) 5.Lee, S.H., and Blair, I.A.Characterization of 4-oxo-2-nonenal as a novel product of lipid peroxidationChemical Research in Toxicology13698-702(2000) 6.Spiteller, P., Kern, W., Reiner, J., et al.Aldehydic lipid peroxidation products derived from linoleic acidBiochimica et Biophysica Acta1531188-208(2001) 7.Liu, Z., Minkler, P.E., and Sayre, L.M.Mass spectroscopic characterization of protein modification by 4-hydroxy-2-(E)-nonenal and 4-oxo-2-(E)-nonenalChemical Research in Toxicology16901-911(2003) 8.Zhang, W.H., Liu, J., Xu, G., et al.Model studies on protein side chain modification by 4-oxo-2-nonenalChemical Research in Toxicology16512-523(2003)