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 |
|---|---|---|
| A prostaglandin J2 metabolite binds peroxisome proliferator-activated receptor gamma and promotes adipocyte differentiation. | 1995 Dec 1 |
|
| Fatty acids and eicosanoids regulate gene expression through direct interactions with peroxisome proliferator-activated receptors alpha and gamma. | 1997 Apr 29 |
|
| Inhibition of nuclear factor kappa B by prostaglandin A1: an effect associated with heat shock transcription factor activation. | 1997 Jan 21 |
|
| Development of a scintillation proximity assay for peroxisome proliferator-activated receptor gamma ligand binding domain. | 1998 Mar 15 |
|
| Expression of peroxisomal proliferator-activated receptors and retinoid X receptors in the kidney. | 1999 Dec |
|
| Effects of peroxisome proliferator-activated receptor agonists on LPS-induced neuronal death in mixed cortical neurons: associated with iNOS and COX-2. | 2002 Jun 21 |
|
| Cyclooxygenase-2 expression by nonsteroidal anti-inflammatory drugs in human airway smooth muscle cells: role of peroxisome proliferator-activated receptors. | 2003 Jan 15 |
|
| Peroxisome proliferator-activated receptor ligands affect growth-related gene expression in human leukemic cells. | 2003 Jun |
|
| 15-deoxy prostaglandin J2 enhances allyl alcohol-induced toxicity in rat hepatocytes. | 2004 Feb |
|
| Differential regulation of chemokine expression by peroxisome proliferator-activated receptor gamma agonists: interactions with glucocorticoids and beta2-agonists. | 2005 Jan 28 |
|
| Covalent binding of 15-deoxy-delta12,14-prostaglandin J2 to PPARgamma. | 2005 Nov 18 |
|
| PPARalpha agonists inhibit nitric oxide production by enhancing iNOS degradation in LPS-treated macrophages. | 2007 Dec |
|
| 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 Sep |
|
| 15-Deoxy-Delta(12,14)-prostaglandin J(2) induces mitochondrial-dependent apoptosis through inhibition of PKA/NF-kappaB in renal proximal epithelial cells. | 2009 Apr 5 |
|
| Selenoprotein-dependent up-regulation of hematopoietic prostaglandin D2 synthase in macrophages is mediated through the activation of peroxisome proliferator-activated receptor (PPAR) gamma. | 2011 Aug 5 |
|
| Tanshinone IIA attenuates atherosclerosis in ApoE(-/-) mice through down-regulation of scavenger receptor expression. | 2011 Jan 10 |
|
| Stable reporter cell lines for peroxisome proliferator-activated receptor γ (PPARγ)-mediated modulation of gene expression. | 2011 Jul 1 |
|
| 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 Jul 8 |
|
| Peroxisome Proliferator-activated receptor γ activation by ligands and dephosphorylation induces proprotein convertase subtilisin kexin type 9 and low density lipoprotein receptor expression. | 2012 Jul 6 |
|
| Sodium dodecyl sulfate and sodium dodecyl benzenesulfonate are ligands for peroxisome proliferator-activated receptor γ. | 2013 |
|
| COX-2 and PPAR-γ confer cannabidiol-induced apoptosis of human lung cancer cells. | 2013 Jan |
|
| PPARγ agonists regulate tobacco smoke-induced Toll like receptor 4 expression in alveolar macrophages. | 2014 Mar 11 |
|
| Manganese superoxide dismutase is a promising target for enhancing chemosensitivity of basal-like breast carcinoma. | 2014 May 20 |
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
Sat Dec 16 07:59:45 GMT 2023
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on
Sat Dec 16 07:59:45 GMT 2023
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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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