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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

5-iPF2α-VI-d11

Cayman Chemical Item Number 10006654

5-iPF2α-VI-d11

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Description

5-iPF2α-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-iPF2α-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 iPF2α-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-PGF2α, iPF2α-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 iPF2α-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 mechanism. Proc Natl Acad Sci USA 87 9383-9387 (1990).

2 Parchmann, S., and Mueller, M.J. Evidence for the formation of dinor isoprostanes E1 from α-linolenic acid in plants. J Biol Chem 273 32650-32655 (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 vivo. Br J Clin Pharmacol 42 15-19 (1996).

4 Reilly, M.P., Barry, P., Lawson, J.A., et al. Urinary 8-epi PGF2α: An index of oxidant stress in vivo. Fibrinolysis & Proteolysis 11 81-84 (1997).

5 Reilly, M.P., Pratico, D., Delanty, N., et al. Increased formation of distinct F2 isoprostanes in hypercholesterolemia. Circulation 98 2822-2828 (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 urine. Proc Natl Acad Sci USA 96(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 urine. J Biol Chem 273 29295-29301 (1998).

8 Praticò, D., Barry, O.P., Lawson, J.A., et al. IPF2α-I: An index of lipid peroxidation in humans. Proc Natl Acad Sci USA 95 3449-3454 (1998).

Formal Name (±)5,​9α,​11α-​trihydroxy-​(8β)-​prosta-​6E,​14Z-​dien-​1-​oic-​16,​16,​17,​17,​18,​18,​19,​19,​20,​20,​20-​d11 acid
Molecular Formula C20H23D11O5
Formula Weight 365.6
Formulation A solution in ethanol
Purity ≥99% deuterated product
Stability 1 year
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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CCCCC/C=C\C[C@H]​1C(O)​CC(O)​[C@H]​1\C=C\C(O)​CCCC(=O)​O

Background Reading

Delanty, N., Reilly, M., Pratico, D., et al. 8-Epi PGF2α: Specific analysis of an isoeicosanoid as an index of oxidant stress in vivo. Br J Clin Pharmacol 42 15-19 (1996).

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 urine. J Biol Chem 273 29295-29301 (1998).

Reilly, M.P., Pratico, D., Delanty, N., et al. Increased formation of distinct F2 isoprostanes in hypercholesterolemia. Circulation 98 2822-2828 (1998).

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 urine. Proc Natl Acad Sci USA 96(23) 13381-13386 (1999).

Parchmann, S., and Mueller, M.J. Evidence for the formation of dinor isoprostanes E1 from α-linolenic acid in plants. J Biol Chem 273 32650-32655 (1998).

Praticò, D., Barry, O.P., Lawson, J.A., et al. IPF2α-I: An index of lipid peroxidation in humans. Proc Natl Acad Sci USA 95 3449-3454 (1998).

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 mechanism. Proc Natl Acad Sci USA 87 9383-9387 (1990).

Reilly, M.P., Barry, P., Lawson, J.A., et al. Urinary 8-epi PGF2α: An index of oxidant stress in vivo. Fibrinolysis & Proteolysis 11 81-84 (1997).

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Size Price Quantity Subtotal
10 µg $149.00 $0.00
25 µg $354.00 $0.00
50 µg $671.00 $0.00
100 µg $1,192.00 $0.00
Bulk Contact
Cart Total $0.00

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Pricing updated 2012-02-10. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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