A metabolite of PGE2
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15-keto Prostaglandin E2

Item No. 14720

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9,15-dioxo-11α-hydroxy-prosta-5Z,13E-dien-1-oic acid
CAS Number
26441-05-4
Synonyms
  • 15-keto PGE2
  • 15-oxo PGE2
Molecular Formula
C20H30O5
Formula Weight
350.5
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: >100 mg/ml (from PGE2)DMSO: >100 mg/ml (from PGE2)Ethanol: >100 mg/ml (from PGE2)PBS pH 7.2: >5 mg/ml (from PGE2)
λmax
229 nm
SMILES
O[C@H]1[C@H](/C=C/C(CCCCC)=O)[C@@H](C/C=C\CCCC(O)=O)C(C1)=O
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
InChi Key
YRTJDWROBKPZNV-KMXMBPPJSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 µg

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    Product Description

    15-keto Prostaglandin E2 (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

    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).

    Product Citations

    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).

    Meriwether, D., Sulaiman, D., Volpe, C., et al. Apolipoprotein A-I mimetics mitigate intestinal inflammation in COX2-dependent inflammatory bowel disease model. J. Clin. Invest. 130, 3670-3685 (2019).

    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).

    Sorgi, C.A., Peti, A.P.F., Petta, T., et al. Comprehensive high-resolution multiple-reaction monitoring mass spectrometry for targeted eicosanoid assays. Sci. Data 5, 180167 (2018).

    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).

    Parker, C.G., Galmozzi, A., Wang, Y., et al. Ligand and target discovery by fragment-based screening in human cells. Cell 168(3), 527-541.e529 (2017).