8-iso Prostaglandin F2α-d4 (Synonyms: iPF2αIIId4, 8Isoprostaned4, 15F2tIsoprostaned4, 8epi PGF2αd4)

8-iso PGF_2α-d₄ contains four deuterium atoms at the 3, 3', 4, and 4' positions. It is intended for use as an internal standard for the quantification of 8-iso PGF_2α by GC- or LC-mass spectrometry. 8-iso Prostaglandin F_2α (8-iso PGF_2α) is an isoprostane produced by the non-enzymatic peroxidation of arachidonic acid in membrane phospholipids.^1,2,3 It circulates in human plasma in two distinct forms - esterified in LDL phospholipids and as the free acid. The ratio of these two forms is approximately 2:1, with a total plasma 8-iso PGF_2α level of about 150 pg/ml in normal volunteers. In normal human urine, 8-iso PGF_2α levels are about 180-200 pg/mg of creatinine.^1,2 8-iso PGF_2α is a weak TP receptor agonist in vascular smooth muscle.⁴ Conversely, 8-iso PGF_2α inhibits platelet aggregation induced by U-46619 (10^-6 M) and I-BOP (3 x 10^-7 M) with IC₅₀ values of 1.6 x 10^-6 M and 1.8 x 10^-6 M, respectively.³

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.Morrow, J.D., Harris, T.M., and Roberts, L.J., IINoncyclooxygenase oxidative formation of a series of novel prostaglandins: Analytical ramifications for measurement of eicosanoidsAnal. Biochem.184(1)1-10(1990) 3.Morrow, J.D., Minton, T.A., and Roberts, L.J., IIThe F2-isoprostane, 8-epi-prostaglandin F2α, a potent agonist of the vascular thromboxane/endoperoxide receptor, is a platelet thromboxane/endoperoxide receptor antagonistProstaglandins44(2)155-163(1992) 4.Kiriyama, M., Ushikubi, F., Kobayashi, T., et al.Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cellsBr. J. Pharmacol.122(2)217-224(1997)