An internal standard for the quantification of 8-iso prostaglandin F2α
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Unlabeled Version(s)
163508-iso Prostaglandin F2α
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8-iso Prostaglandin F2α-d4

Item No. 316350

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9α,11α,15S-trihydroxy-(8β)-prosta-5Z,13E-dien-1-oic-3,3,4,4-d4 acid
CAS Number
211105-40-7
Synonyms
  • iPF2α-III-d4
  • 8-Isoprostane-d4
  • 15-F2t-Isoprostane-d4
  • 8-epi PGF2α-d4
Molecular Formula
C20H30D4O5
Formula Weight
358.5
Purity
≥99% deuterated forms (d1-d4)
Formulation
A 100 µg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
10 mM Na2CO3: >6.5 mg/mlDMF: >100 mg/mlDMSO: >100 mg/mlEthanol: >100 mg/mlPBS pH 7.2: >10 mg/ml
SMILES
O[C@@H]1[C@@H](C/C=C\C([2H])([2H])C([2H])([2H])CC(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/i5D2,8D2
InChi Key
PXGPLTODNUVGFL-FLRLWOSLSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 µg

    $219

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    50 µg

    $416

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    100 µg

    $788

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    Product Description

    8-iso PGF2α-d4 is intended for use as an internal standard for the quantification of 8-iso PGF2α by GC- or LC-mass spectrometry. 8-iso Prostaglandin F2α (8-iso PGF2α) 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 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

    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).