(±)5-iPF2α-VI-d11

(±)5-iPF_2α-VI-d₁₁ contains 11 deuterium atoms at the 16, 16, 17, 17, 18, 18, 19, 19, 20, 20, and 20 positions. It is intended for use as an internal standard for the quantification of (±)5-iPF_2α-VI by GC- or LC-mass spectrometry. Isoprostanes are prostaglandin-like products of free-radical induced lipid peroxidation.¹ Although the isoprostanes derived from arachidonic acid are the best characterized, many other polyunsaturated fatty acids can form isoprostanes.² iPF_2α-VI is one of dozens of possible stereo- and regioisomeric isoprostanes which can be formed from arachidonic acid. To date, the most extensively studied of these is 8-isoprostane (8-epi-PGF_2α, iPF_2α-III).^3,4 However, 8-isoprostane is a minor isoprostane constituent when compared to some of the other isomers which form in natural conditions of oxidative stress,⁵ including iPF_2α-VI of the type-VI isoprostanes. This class has been shown to be one of the major isoprostane products, in contrast to 8-isoprostane. In addition to being produced in greater abundance than 8-isoprostane, Type VI isoprostanes form internal lactones which facilitate their extraction and purification from biological samples.^5,6,7,8

1.Morrow, J.D., Hill, K.E., Burk, R.F., et al.A series of prostaglandin F2-like compounds are produced in vivo in humans by a non-cyclooxygenase, free radical-catalyzed mechanismProc. Natl. Acad. Sci. U.S.A.87(23)9383-9387(1990) 2.Parchmann, S., and Mueller, M.J.Evidence for the formation of dinor isoprostanes E1 from α-linolenic acid in plantsThe Journal of Biological Chemisty27332650-32655(1998) 3.Delanty, N., Reilly, M., Pratico, D., et al.8-Epi PGF2α: Specific analysis of an isoeicosanoid as an index of oxidant stress in vivoBritish Journal of Clinical Pharmacology4215-19(1996) 4.Reilly, M.P., Barry, P., Lawson, J.A., et al.Urinary 8-epi PGF2α: An index of oxidant stress in vivoFibrinolysis & Proteolysis1181-84(1997) 5.Reilly, M.P., Pratico, D., Delanty, N., et al.Increased formation of distinct F2 isoprostanes in hypercholesterolemiaCirculation982822-2828(1998) 6.Li, H., Lawson, J.A., Reilly, M., et al.Quantitative high performance liquid chromatography/tandem mass spectrometric analysis of the four classes of F2-isoprostanes in human urineProceedings of the National Academy of Sciences of the United States of America96(23)13381-13386(1999) 7.Lawson, J.A., Li, H., Rokach, J., et al.Identification of two major F2 isoprostanes, 8,12-iso- and 5-epi-8,12-iso-isoprostane F2α-VI, in human urineThe Journal of Biological Chemisty27329295-29301(1998) 8.PraticÒ, D., Barry, O.P., Lawson, J.A., et al.IPF2α-I: An index of lipid peroxidation in humansProceedings of the National Academy of Sciences of the United States of America953449-3454(1998)