An isoprostane that inhibits platelet aggregation
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8-iso Prostaglandin F2α

Item No. 16350

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9α,11α,15S-trihydroxy-(8β)-prosta-5Z,13E-dien-1-oic acid
CAS Number
27415-26-5
Synonyms
  • iPF2α-III
  • 8-iso-15(S)-Prostaglandin F2α
  • 8-Isoprostane
  • 8-epi PGF2α
  • 15-F2t-Isoprostane
Molecular Formula
C20H34O5
Formula Weight
354.5
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: >100 mg/mlDMSO: >100 mg/mlEthanol: >100 mg/mlPBS pH 7.2: 3 mg/ml
SMILES
O[C@@H]1[C@@H](C/C=C\CCCC(O)=O)[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C1
InChi Code
InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16-,17+,18-,19+/m0/s1
InChi Key
PXGPLTODNUVGFL-NAPLMKITSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    8-iso PGF2α is an isoprostane produced by the non-enzymatic peroxidation of arachidonic acid in membrane phospholipids.1,2,3 It is present in human plasma in two distinct forms - esterified in phospholipids and as the free acid. The ratio of these two forms is approximately 2:1, with a total plasma 8-iso PGF2α level of about 150 pg/ml in normal volunteers. In normal human urine, 8-iso PGF2α levels are about 180-200 pg/mg of creatinine.1,2 8-iso PGF2α is a weak TP receptor agonist in vascular smooth muscle.4 Conversely, 8-iso PGF2α 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

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    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(23), 9383-9387 (1990).

    2. Morrow, J.D., Harris, T.M., and Roberts, L.J., II Noncyclooxygenase oxidative formation of a series of novel prostaglandins: Analytical ramifications for measurement of eicosanoids. Anal. Biochem. 184(1), 1-10 (1990).

    3. Morrow, J.D., Minton, T.A., and Roberts, L.J., II The F2-isoprostane, 8-epi-prostaglandin F2α, a potent agonist of the vascular thromboxane/endoperoxide receptor, is a platelet thromboxane/endoperoxide receptor antagonist. Prostaglandins 44(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 cells. Br. J. Pharmacol. 122(2), 217-224 (1997).

    Product Citations

    Hartling, I., Cremonesi, A., Osuna, E., et al. Quantitative profiling of inflammatory and pro-resolving lipid mediators in human adolescents and mouse plasma using UHPLC-MS/MS. Clin. Chem. Lab. Med. 59(11), 1811-1823 (2021).

    Sasaki, A., Fukuda, H., Shiida, N., et al. Determination of ω-6 and ω-3 PUFA metabolites in human urine samples using UPLC/MS/MS. Anal. Bioanal. Chem. 407(6), 1625-1639 (2015).

    Jovanović, V., Aziz, N.A., Lim, Y.T., et al. Lipid anti-lipid antibody responses correlate with disease activity in systemic lupus erythematosus. PLoS one 8(2), e55639 (2013).

    Opere, C.A., Zheng, W.D., Huang, J., et al. Dual effect of isoprostanes on the release of [3H]D-aspartate from isolated bovine retinae: Role of arachidonic acid metabolites. Neurochem. Res. 30(1), 129-137 (2005).

    Basu, S., Smedman, A., and Vessby, B. Conjugated linoleic acid induces lipid peroxidation in humans. FEBS Lett. 468(1), 33-36 (2000).