4-hydroxy Nonenal Glutathione-d3 (trifluoroacetate salt)

4-hydroxy Nonenal Glutathione-d₃ (4-HNE-GSH-d₃ (trifluoroacetate salt) contains three deuterium atoms at the terminal methyl position. It is intended for use as an internal standard for the quantification of 4-HNE-GSH (trifluoroacetate salt) by GC- or LC-mass spectrometry. 4-hydroxy-Nonenal (4-HNE) is a major aldehyde produced during the lipid peroxidation of ω-6 polyunsaturated fatty acids, such as arachidonic acid and linoleic acid.^1,2 4-HNE-GSH is a major adduct formed by the reaction of 4-HNE with GSH.^3,4,5,6 4-HNE-GSH levels in liver, plasma, or isolated cells can serve as biomarkers for oxidative stress.⁷ The trapping of 4-HNE by glutathione to give HNE-GSH prevents the formation of DNA adducts with 4-HNE.^8,9 In human polymorphonuclear leukocytes, HNE-GSH is metabolized to 1,4-dihydroxynonene glutathione (DHN-GSH), 4-hydroxynonenoic acid glutathione (HNA-GSH), and 4-hydroxy nonenal mercapturic acid (HNE-MA).³

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.Siems, W., Crifo, C., Capuozzo, E., et al.Metabolism of 4-hydroxy-2-nonenal in human polymorphonuclear leukocytesArchives of Biochemistry and Biophysics503248-252(2010) 4.Laurent, A., Alary, J., Debrauwer, L., et al.Analysis in the rat of 4-hydroxynonenal metabolites excreted in bile: Evidence of enterohepatic circulation of these byproducts of lipid peroxidationChemical Research in Toxicology12887-894(1999) 5.Siems, W., and Grune, T.Intracellular metabolism of 4-hydroxynonenalMol.Aspects Med.24167-175(2003) 6.Alary, J., Fernandez, Y., Debrauwer, L., et al.Identification of intermediate pathways of 4-hydroxynonenal metabolism in the ratChemical Research in Toxicology16320-327(2003) 7.VÖlkel, W., Alvarez-SÁnchez, R., Weick, I., et al.Glutathione conjugates of 4-hydroxy-2(E)-nonenal as biomarkers of hepatic oxidative stress-induced lipid peroxidation in ratsFree Radical Biology & Medicine381526-1536(2005) 8.King, A.O., Corley, E.G., Anderson, R.K., et al.An efficient synthesis of LTD4 antagonist L-699,392The Journal of Organic Chemistry583731-3735(1993) 9.Falletti, O., Cadet, J., Favier, A., et al.Trapping of 4-hydroxynonenal by glutathione efficiently prevents formation of DNA adducts in human cellsFree Radical Biology & Medicine421258-1269(2007)