15-keto Prostaglandin E2

15-keto Prostaglandin E2 (15-keto PGE2) is a metabolite of PGE2 (Cay-14010) formed by 15-hydroxy prostaglandin dehydrogenase (15-PGDH). 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 beta-catenin/TCF in the same cells. 15-keto PGE2 inhibits CD3-CD28-MHC-I-induced proliferation of isolated human CD4+ T cells in a concentration-dependent manner. It also reduces mortality in a mouse model of LPS-induced sepsis when administered at a dose of 15 mg/kg.Formal Name: 9,15-dioxo-11alpha-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: 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). lambdamax: 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.