A metabolite of PGE2
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13,14-dihydro-15-keto Prostaglandin E2

Item No. 14650

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5Z,11α)-11-hydroxy-9,15-dioxo-prost-5-en-1-oic acid
CAS Number
363-23-5
Synonyms
  • 13,14-dihydro-15-keto PGE2
  • 13,14-dihydro-oxo-PGE2
  • PGEM
Molecular Formula
C20H32O5
Formula Weight
352.5
Purity
≥95%
Formulation (Request formulation change)
A 10 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: >100 mg/mlDMSO: >100 mg/mlEthanol: >100 mg/mlPBS (pH 7.2): >5 mg/ml
SMILES
O=C1[C@H](C/C=C\CCCC(O)=O)[C@@H](CCC(CCCCC)=O)[C@H](O)C1
InChi Code
InChI=1S/C20H32O5/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/h4,7,16-17,19,23H,2-3,5-6,8-14H2,1H3,(H,24,25)/b7-4-/t16-,17-,19-/m1/s1
InChi Key
CUJMXIQZWPZMNQ-XYYGWQPLSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    13,14-dihydro-15-keto Prostaglandin E2 (13,14-dihydro-15-keto PGE2) is a metabolite of PGE2 (Item No. 14010) and the primary PGE2 metabolite in plasma.1,2 It is formed from PGE2 via a 15-keto PGE2 intermediate by 15-oxo-PG Δ13 reductase.2 Unlike PGE2, 13,14-dihydro-15-keto PGE2 does not bind effectively to the PGE2 receptors EP2 and EP4 expressed in CHO cells (Kis = 12 and 57 µM, respectively) or induce adenylate cyclase activity in the same cells (EC50s = >18 and >38 µM, respectively). Levels of 13,14-dihydro-15-keto PGE2 are increased in the plasma of women in the third trimester of pregnancy and in women during and immediately after labor and delivery.3 Levels of 13,14-dihydro-15-keto PGE2 levels are decreased in tumor tissue compared to adjacent non-cancerous tissue isolated from patients with non-small cell lung cancer (NSCLC).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hamberg, M., and Samuelsson, B. On the metabolism of prostaglandins E1 and E2 in man. The Journal of Biological Chemisty 246(22), 6713-6721 (1971).

    2. 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).

    3. Husslein, P., and Sinzinger, H. Concentration of 13,14-dihydro-15-keto-prostaglandin E2 in the maternal peripheral plasma during labour of spontaneous onset. Br. J. Obstet. Gynaecol. 91(3), 228-231 (1984).

    4. Hughes, D., Otani, T., Yang, P., et al. NAD+-dependent 15-hydroxyprostaglandin dehydrogenase regulates levels of bioactive lipids in non-small cell lung cancer. Cancer Prev. Res. (Phila.) 1(4), 241-249 (2008).

    Product Citations

    Maric, J., Ravindran, A., Mazzurana, L., et al. Cytokine-induced endogenous production of prostaglandin D2 is essential for human group 2 innate lymphoid cell activation. J. Allergy Clin. Immunol. 143(6), 2202-2214 (2019).

    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).