An internal standard for the quantification of PGE2
Related Products
Alternative(s)
1934915-keto Prostaglandin E2-d4
Unlabeled Version(s)
1472015-keto Prostaglandin E2
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15-keto Prostaglandin E2-d9

Item No. 19350

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(Z)-7-((1R,2R,3R)-3-hydroxy-5-oxo-2-((E)-3-oxooct-1-en-1-yl-5,5,6,6,7,7,8,8,8-d9)cyclopentyl)hept-5-enoic acid
CAS Number
2738376-66-2
Synonyms
  • 15-keto PGE2-d9
  • 15-oxo PGE2-d9
Molecular Formula
C20H21D9O5
Formula Weight
359.5
Purity
≥99% deuterated forms (d1-d9)
Formulation
A 500 µg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMSO: 50 mg/mlEthanol: 50 mg/mlPBS (pH 7.2): 1 mg/ml
SMILES
O=C1[C@H](C/C=C\CCCC(O)=O)[C@@H](/C=C/C(CC([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])[2H])=O)[C@H](O)C1
InChi Code
InChI=1S/C20H30O5/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/h4,7,12-13,16-17,19,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t16-,17-,19-/m1/s1/i1D3,2D2,3D2,6D2
InChi Key
YRTJDWROBKPZNV-AEVDOOJTSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    50 µg

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    Product Description

    15-keto Prostaglandin E2-d9 (15-keto PGE2-d9) is intended for use as an internal standard for the quantification of 15-keto PGE2 (Item No. 14720) by GC- or LC-MS. 15-keto PGE2 is a metabolite of PGE2 (Item No. 14010) formed by 15-hydroxy prostaglandin dehydrogenase (15-PGDH).1 Unlike PGE2, 15-keto PGE2 does not bind effectively to the PGE2 receptors EP2 and EP4 expressed in CHO cells (Kis = 2.6 and 15 µM, respectively) or induce adenylate cyclase activity in the same cells (EC50s = 1.8 and >33 µM, respectively). However, it does bind to EP2 and EP4 in HEK cells expressing these receptors (IC50s = 0.117 and 2.82 µM, respectively), as well as induces cAMP formation (EC50s = 0.137 and 0.426 µM, respectively) and the transcriptional activity of β-catenin/TCF in the same cells.2 15-keto PGE2 inhibits CD3-CD28-MHC-I-induced proliferation of isolated human CD4+ T cells in a concentration-dependent manner.3 It also reduces mortality in a mouse model of LPS-induced sepsis when administered at a dose of 15 mg/kg.4 a Kd = 1 nM for PGE2).1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nishigaki, N., Negishi, M., and Ichikawa, A. Two Gs-coupled prostaglandin E receptor subtypes, EP2 and EP4, differ in desensitization and sensitivity to the metabolic inactivation of the agonist. Mol. Pharmacol. 50(4), 1031-1037 (1996).

    2. Endo, S., Suganami, A., Fukushima, K., et al. 15-Keto-PGE2 acts as a biased/partial agonist to terminate PGE2-evoked signaling. The Journal of Biological Chemisty 295(38), 13338-13352 (2020).

    3. Schmidleithner, L., Thabet, Y., Schönfeld, E., et al. Enzymatic activity of HPGD in Treg cells suppresses Tconv cells to maintain adipose tissue homeostasis and prevent metabolic dysfunction. Immunity 50(5), 1232-1248 (2019).

    4. Chen, I.-J., Hee, S.-W., Liao, C.-H., et al. Targeting the 15-keto-PGE2-PTGR2 axis modulates systemic inflammation and survival in experimental sepsis. Free Radic. Biol. Med. 115, 113-126 (2018).