15-keto Prostaglandin E2-d4

15-keto Prostaglandin E2-d4 (15-keto PGE2-d4) is intended for use as an internal standard for the quantification of 15-keto PGE2 (Cay-14720) by GC- or LC-MS. 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-11a-hydroxy-prosta-5Z,13E-dien-1-oic-3,3,4,4-d4 acid. CAS Number: 2738376-85-5. Synonyms: 15-keto PGE2-d4, 15-oxo PGE2-d4. Molecular Formula: C20H26D4O5. Formula Weight: 354.5. Purity: >99% deuterated forms (d1-d4). Formulation: (Request formulation change), A solution in methyl acetate. Solubility: DMF: 50 mg/ml, DMSO: 50 mg/ml, Ethanol: 50 mg/ml, PBS (pH 7.2): 1 mg/ml. SMILES: O=C1[C@H](C/C=C\C([2H])([2H])C([2H])([2H])CC(O)=O)[C@@H](/C=C/C(CCCCC)=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/i5D2,8D2. InChi Key: YRTJDWROBKPZNV-BXMNJGIBSA-N.