Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H28O3 |
| Molecular Weight | 316.4345 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 3 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCC\C=C\C=C1/[C@@H](C\C=C/CCCC(O)=O)C=CC1=O
InChI
InChIKey=VHRUMKCAEVRUBK-GODQJPCRSA-N
InChI=1S/C20H28O3/c1-2-3-4-5-6-10-13-18-17(15-16-19(18)21)12-9-7-8-11-14-20(22)23/h6-7,9-10,13,15-17H,2-5,8,11-12,14H2,1H3,(H,22,23)/b9-7-,10-6+,18-13+/t17-/m0/s1
| Molecular Formula | C20H28O3 |
| Molecular Weight | 316.4345 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 3 |
| Optical Activity | UNSPECIFIED |
15-deoxy-Δ12,14-Prostaglandin J2 (15d-PGJ2) is a cyclopentanone prostaglandin and the agonist of endogenous PPAR gamma ligand, that is formed via the elimination of two molecules of water of prostaglandin D2. 15d-PGJ2 possesses anti-inflammatory effects. Experiments with animal models revealed, that 15d-PGJ2 may represent a potential therapeutic strategy in rheumatoid arthritis. Besides, 15d-PGJ2, given either systemically or locally in mice can control ongoing asthma pathological abnormalities, including eosinophil and neutrophil infiltration, mucus exacerbation, and lung remodeling triggered by ovalbumin. It was suggested, that potential exists to exploit 15d-PGJ2 as a therapeutic agent in asthma. It is known, the determination of individual prostaglandins, including 15d-PGJ2 in urine samples could improve the understanding of particular prostaglandins species under various physiological and pathological conditions. Recently was suggested the sensitive method for determination of 15d-PGJ2 and its application in human plasma samples of patients with diabetes.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P37231|||Q15179 Gene ID: 5468.0 Gene Symbol: PPARG Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Palliative | Unknown Approved UseUnknown |
|||
| Palliative | Unknown Approved UseUnknown |
|||
| Diagnostic | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Manganese superoxide dismutase is a promising target for enhancing chemosensitivity of basal-like breast carcinoma. | 2014-05-20 |
|
| PPARγ agonists regulate tobacco smoke-induced Toll like receptor 4 expression in alveolar macrophages. | 2014-03-11 |
|
| COX-2 and PPAR-γ confer cannabidiol-induced apoptosis of human lung cancer cells. | 2013-01 |
|
| Sodium dodecyl sulfate and sodium dodecyl benzenesulfonate are ligands for peroxisome proliferator-activated receptor γ. | 2013 |
|
| Peroxisome Proliferator-activated receptor γ activation by ligands and dephosphorylation induces proprotein convertase subtilisin kexin type 9 and low density lipoprotein receptor expression. | 2012-07-06 |
|
| Selenoprotein-dependent up-regulation of hematopoietic prostaglandin D2 synthase in macrophages is mediated through the activation of peroxisome proliferator-activated receptor (PPAR) gamma. | 2011-08-05 |
|
| 15-Deoxy-Δ12,14-prostaglandin J2 enhanced the anti-tumor activity of camptothecin against renal cell carcinoma independently of topoisomerase-II and PPARγ pathways. | 2011-07-08 |
|
| Stable reporter cell lines for peroxisome proliferator-activated receptor γ (PPARγ)-mediated modulation of gene expression. | 2011-07-01 |
|
| 15-Deoxy-delta12,14-prostaglandin J2-glycerol ester, a putative metabolite of 2-arachidonyl glycerol, activates peroxisome proliferator activated receptor gamma. | 2011-07 |
|
| Molecular mechanisms underlying the inhibition of IFN-γ-induced, STAT1-mediated gene transcription in human macrophages by simvastatin and agonists of PPARs and LXRs. | 2011-02 |
|
| Tanshinone IIA attenuates atherosclerosis in ApoE(-/-) mice through down-regulation of scavenger receptor expression. | 2011-01-10 |
|
| Aspirin inhibits MMP-9 mRNA expression and release via the PPARalpha/gamma and COX-2/mPGES-1-mediated pathways in macrophages derived from THP-1 cells. | 2010-02 |
|
| 15-Deoxy-Delta(12,14)-prostaglandin J(2) induces mitochondrial-dependent apoptosis through inhibition of PKA/NF-kappaB in renal proximal epithelial cells. | 2009-04-05 |
|
| Reduction of nuclear peroxisome proliferator-activated receptor gamma expression in methamphetamine-induced neurotoxicity and neuroprotective effects of ibuprofen. | 2009-04 |
|
| Ajulemic acid, a synthetic cannabinoid acid, induces an antiinflammatory profile of eicosanoids in human synovial cells. | 2008-11-07 |
|
| The hepatotoxic metabolite of acetaminophen directly activates the Keap1-Nrf2 cell defense system. | 2008-10 |
|
| Curcumin inhibits connective tissue growth factor gene expression in activated hepatic stellate cells in vitro by blocking NF-kappaB and ERK signalling. | 2008-02 |
|
| PPARalpha agonists inhibit nitric oxide production by enhancing iNOS degradation in LPS-treated macrophages. | 2007-12 |
|
| Apoptotic action of peroxisome proliferator-activated receptor-gamma activation in human non small-cell lung cancer is mediated via proline oxidase-induced reactive oxygen species formation. | 2007-09 |
|
| Peroxisome proliferator-activated receptor-gamma agonists inhibit respiratory syncytial virus-induced expression of intercellular adhesion molecule-1 in human lung epithelial cells. | 2007-05 |
|
| Up-regulation of skeletal muscle LIM protein 1 gene by 25-hydroxycholesterol may mediate morphological changes of rat aortic smooth muscle cells. | 2007-01-09 |
|
| Peroxisome proliferated-activated receptor gamma ligand, Pioglitazone, does not prevent hepatic fibrosis in mice. | 2007-01 |
|
| Cardiomyocytic apoptosis following global cardiac ischemia and reperfusion can be attenuated by peroxisome proliferator-activated receptor alpha but not gamma activators. | 2006-09 |
|
| Piceatannol upregulates endothelial heme oxygenase-1 expression via novel protein kinase C and tyrosine kinase pathways. | 2006-02 |
|
| Rosiglitazone and 15-deoxy-Delta12,14-prostaglandin J2 cause potent neuroprotection after experimental stroke through noncompletely overlapping mechanisms. | 2006-02 |
|
| Covalent binding of 15-deoxy-delta12,14-prostaglandin J2 to PPARgamma. | 2005-11-18 |
|
| Peroxisome proliferator-activated receptor-gamma ligands suppress fibronectin gene expression in human lung carcinoma cells: involvement of both CRE and Sp1. | 2005-09 |
|
| Troglitazone and 15-deoxy-delta(12,14)-prostaglandin J2 inhibit shear-induced coupling factor 6 release in endothelial cells. | 2005-07-01 |
|
| The selective cyclooxygenase-2 inhibitor SC-236 reduces liver fibrosis by mechanisms involving non-parenchymal cell apoptosis and PPARgamma activation. | 2005-07 |
|
| Differential regulation of chemokine expression by peroxisome proliferator-activated receptor gamma agonists: interactions with glucocorticoids and beta2-agonists. | 2005-01-28 |
|
| Inhibition of interleukin-1beta-induced cyclooxygenase 2 expression in human synovial fibroblasts by 15-deoxy-Delta12,14-prostaglandin J2 through a histone deacetylase-independent mechanism. | 2005-01 |
|
| A yeast two-hybrid technology-based system for the discovery of PPARgamma agonist and antagonist. | 2004-12-15 |
|
| 15-deoxy prostaglandin J2 enhances allyl alcohol-induced toxicity in rat hepatocytes. | 2004-02 |
|
| 15-deoxy-delta 12,14-prostaglandin J2 and laminar fluid shear stress stabilize c-IAP1 in vascular endothelial cells. | 2003-07 |
|
| Peroxisome proliferator-activated receptor ligands affect growth-related gene expression in human leukemic cells. | 2003-06 |
|
| Cyclooxygenase-2 expression by nonsteroidal anti-inflammatory drugs in human airway smooth muscle cells: role of peroxisome proliferator-activated receptors. | 2003-01-15 |
|
| Ligands of the peroxisome proliferator-activated receptors (PPAR-gamma and PPAR-alpha) reduce myocardial infarct size. | 2002-07 |
|
| Natural ligands of PPARgamma: are prostaglandin J(2) derivatives really playing the part? | 2002-07 |
|
| Effects of peroxisome proliferator-activated receptor agonists on LPS-induced neuronal death in mixed cortical neurons: associated with iNOS and COX-2. | 2002-06-21 |
|
| Nimesulide, a preferential cyclooxygenase 2 inhibitor, suppresses peroxisome proliferator-activated receptor induction of cyclooxygenase 2 gene expression in human synovial fibroblasts: evidence for receptor antagonism. | 2002-02 |
|
| Unique ability of troglitazone to up-regulate peroxisome proliferator-activated receptor-gamma expression in hepatocytes. | 2002-01 |
|
| Inhibition of phosphoenolpyruvate carboxykinase (PEPCK) gene expression by troglitazone: a peroxisome proliferator-activated receptor-gamma (PPARgamma)-independent, antioxidant-related mechanism. | 2001-10-15 |
|
| Two opposing effects of non-steroidal anti-inflammatory drugs on the expression of the inducible cyclooxygenase. Mediation through different signaling pathways. | 2000-09-08 |
|
| Expression of peroxisomal proliferator-activated receptors and retinoid X receptors in the kidney. | 1999-12 |
|
| Development of a scintillation proximity assay for peroxisome proliferator-activated receptor gamma ligand binding domain. | 1998-03-15 |
|
| Fatty acids and eicosanoids regulate gene expression through direct interactions with peroxisome proliferator-activated receptors alpha and gamma. | 1997-04-29 |
|
| Inhibition of nuclear factor kappa B by prostaglandin A1: an effect associated with heat shock transcription factor activation. | 1997-01-21 |
|
| A prostaglandin J2 metabolite binds peroxisome proliferator-activated receptor gamma and promotes adipocyte differentiation. | 1995-12-01 |
Patents
Sample Use Guides
Arthritic mice: were treated with 15-deoxy Δ12,14-prostaglandin J2 (15d-PGJ2) (1 mg/kg) by the s.c. route daily for 7 days
Route of Administration:
Other
To assess the influence of 15-deoxy-Δ12,14-Prostaglandin J2 (15d-PGJ2) treatment on T cell proliferation, popliteal and inguinal lymph nodes cells harvested from arthritic mice were removed and washed twice with PBS. Tissues were minced, and the cells were filtered through a cell strainer, centrifuged at 500 ×g at 4°C for 10 min, and resuspended in RPMI-1640 medium at 2.5 × 106 cells/mL. In some wells, cells were incubated with 15d-PGJ2 (5 μM) or vehicle (DMSO 0.5%) 1 hour before stimulation. The immunosuppressive effect of 15d-PGJ2 on the inflammatory immune response during collagen-induced arthritis was revealed.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 21:48:38 GMT 2025
by
admin
on
Mon Mar 31 21:48:38 GMT 2025
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| Record UNII |
ALI977775J
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| Record Status |
Validated (UNII)
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| Record Version |
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| Related Record | Type | Details | ||
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TARGET -> AGONIST |
Binding Assay
IC50
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