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8-iso Prostaglandin F2α-d4

Cayman Chemical Item Number 316350

15-F2t-Isoprostane-d4; iPF2α-III-d4; 8-epi PGF2α-d4; 8-Isoprostane-d4 (CAS 211105-40-7)

8-iso Prostaglandin F2α-d4 (CAS 211105-40-7)

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Description

8-iso PGF2α-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 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

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

3 Morrow, J.D., Minton, T.A., and Roberts, L.J. The F2-isoprostane, 8-epi-prostaglandin F2α, a potent agonist of the vascular thromboxane/endoperoxide receptor, is a platelet thromboxane/endoperoxide receptor antagonist. Prostaglandins 44 155-163 (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 122 217-224 (1997).

Synonyms
  • 15-F2t-Isoprostane-d4
  • iPF2α-III-d4
  • 8-epi PGF2α-d4
  • 8-Isoprostane-d4
Formal Name 9α,​11α,​15S-​trihydroxy-​(8β)-​prosta-​5Z,​13E-​dien-​1-​oic-​3,​3,​4,​4-​d4 acid
CAS Number 211105-40-7
Molecular Formula C20H30D4O5
Formula Weight 358.5
Formulation A solution in methyl acetate
Purity ≥99% deuterated forms (d1- d4)
Stability 2 years
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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CCCCCC(O)​/C=C/[C@H]​1C(O)​CC(O)​[C@H]​1C/C=C\CCCC(=O)​O

Background Reading

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).

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

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 122 217-224 (1997).

Morrow, J.D., Minton, T.A., and Roberts, L.J. The F2-isoprostane, 8-epi-prostaglandin F2α, a potent agonist of the vascular thromboxane/endoperoxide receptor, is a platelet thromboxane/endoperoxide receptor antagonist. Prostaglandins 44 155-163 (1992).

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Size Price Quantity Subtotal
25 µg $134.00 $0.00
50 µg $255.00 $0.00
100 µg $482.00 $0.00
500 µg $2,144.00 $0.00
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Cart Total $0.00

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Pricing updated 2012-05-26. 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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FAQs

It appears that there is a heterogenous mixture of deuterated species in your deuterated standards; is this normal?

Yes, this is typical of our deuterated products. Our deuterated products contain less than 1 % d0. However, the labeled compounds are not 100% of the deuterated form listed on our product insert. For example, upon analysis of 2-arachidonoyl glycerol-d8 it is expected to see masses associated with the d7, d6, d5 etc.

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