An isoprostane
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8-iso Prostaglandin A2

Item No. 10235

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(8β)-15S-hydroxy-9-oxo-prosta-5Z,10,13E-trien-1-oic acid
CAS Number
474391-66-7
Synonyms
  • A2 Isoprostane
  • 15-A2t-IsoP
  • 15-A2t-Isoprostane
  • 8-epi PGA2
  • 8-iso PGA2
Molecular Formula
C20H30O4
Formula Weight
334.5
Purity
≥98%
Formulation
A 1 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: >75 mg/mlDMSO: >50 mg/mlEthanol: >100 mg/mlPBS pH 7.2: >2.4 mg/ml
λmax
217 nm
SMILES
O=C1[C@@H](C/C=C\CCCC(O)=O)[C@@H](/C=C/[C@@H](O)CCCCC)C=C1
InChi Code
InChI=1S/C20H30O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h4,7,12-18,21H,2-3,5-6,8-11H2,1H3,(H,23,24)/b7-4-,14-12+/t16-,17-,18-/m0/s1
InChi Key
MYHXHCUNDDAEOZ-UKUWKSPLSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    8-iso Prostaglandin A2 (8-iso PGA2) is an isoprostane. It is produced by the non-enzymatic oxidation of arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607).1,2 8-iso PGA2 (100 µM) induces calcium influx in HEK293 cells expressing human transient receptor potential ankyrin 1 (TRPA1) and isolated mouse trigeminal neurons.3 It potentiates glutamate-induced cytotoxicity and decreases glutathione (GSH) levels in HT22 hippocampal cells when used at concentrations of 1 and 30 µM, respectively.4 8-iso PGA2 (10 µM) inhibits VEGF-induced migration and tube formation of human coronary artery endothelial cells, an effect that can be reversed by the TP receptor antagonist SQ 29,548 (Item No. 19025).5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chen, Y., Morrow, J.D., and Roberts, L.J., II Formation of reactive cyclopentenone compounds in Vivo as products of the isoprostane pathway. The Journal of Biological Chemisty 274(16), 10863-10868 (1999).

    2. Chen, Y., Zackert, W.E., Roberts, L.J., II, et al. Evidence for the formation of a novel cyclopentenone isoprostane, 15-A2t-isoprostane (8-iso-prostaglandin A2) in vivo. Biochim. Biophys. Acta 1436(3), 550-556 (1999).

    3. Taylor-Clark, T.E., Undem, B.J., MacGlashan, D.W., Jr., et al. Prostaglandin-induced activation of nociceptive neurons via direct interaction with transient receptor potential A1 (TRPA1). Mol. Pharmacol. 73(2), 274-281 (2008).

    4. Musiek, E.S., Breeding, R.S., Milne, G.L., et al. Cyclopentenone isoprostanes are novel bioactive products of lipid oxidation which enhance neurodegeneration. J. Neurochem. 97, 1301-1313 (2006).

    5. Benndorf, R.A., Schwedhelm, E., Gnann, A., et al. Isoprostanes inhibit vascular endothelial growth factor-induced endothelial cell migration, tube formation, and cardiac vessel sprouting in vitro, as well as angiogenesis in vivo via activation of the thromboxane A2 receptor: A potential link between oxidative stress and impaired angiogenesis. Circ. Res. 103(9), 1037-1046 (2008).