4-hydroxy Nonenal Glutathione-d3 (4-HNE-GSH-d3) is intended for use as an internal standard for the quantification of 4-HNE-GSH by GC- or LC-MS. 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
References:
[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 Radic. Biol. Med.8(6)541-543(1990).
[2]. Esterbauer, H., Schaur, R.J., and Zoliner, H.Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde, and related aldehydesFree Radic. Biol. Med.11(1)81-128(1991).
[3]. Siems, W., Crifo, C., Capuozzo, E., et al.Metabolism of 4-hydroxy-2-nonenal in human polymorphonuclear leukocytesArch. Biochem. Biophys.503(2)248-252(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 peroxidationChem. Res. Toxicol.12(10)887-894(1999).
[5]. Siems, W., and Grune, T.Intracellular metabolism of 4-hydroxynonenalMol. Aspects Med.24(4-5)167-175(2003).
[6]. Alary, J., Fernandez, Y., Debrauwer, L., et al.Identification of intermediate pathways of 4-hydroxynonenal metabolism in the ratChem. Res. Toxicol.16(3)320-327(2003).
[7]. V?lkel, 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 Radic. Biol. Med.38(11)1526-1536(2005).
[8]. King, A.O., Corley, E.G., Anderson, R.K., et al.An efficient synthesis of LTD4 antagonist L-699,392J. Org. Chem.58(14)3731-3735(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 Radic. Biol. Med.42(8)1258-1269(2007).