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Merck

M6191

Sigma-Aldrich

GW9662

>98% (HPLC)

Synonym(e):

2-Chloro-5-nitro-N-phenylbenzamide

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About This Item

Empirische Formel (Hill-System):
C13H9ClN2O3
CAS-Nummer:
Molekulargewicht:
276.68
MDL-Nummer:
UNSPSC-Code:
51111800
PubChem Substanz-ID:
NACRES:
NA.77

Assay

>98% (HPLC)

Form

powder

Farbe

white

Löslichkeit

DMSO: 26 mg/mL
H2O: insoluble

Lagertemp.

2-8°C

SMILES String

[O-][N+](=O)c1ccc(Cl)c(c1)C(=O)Nc2ccccc2

InChI

1S/C13H9ClN2O3/c14-12-7-6-10(16(18)19)8-11(12)13(17)15-9-4-2-1-3-5-9/h1-8H,(H,15,17)

InChIKey

DNTSIBUQMRRYIU-UHFFFAOYSA-N

Angaben zum Gen

human ... PPARG(5468)

Anwendung

GW9662 has been used as a peroxisome proliferator activated receptor γ (PPARγ) antagonist in human pluripotent stem cells, in phenylephrine stimulated cardiomyocytes and to inhibit the protective effect of telmisartan pheochromocytoma, PC12 cells.

Biochem./physiol. Wirkung

GW9662 (2-chloro-5-nitrobenzanilide) binds to the ligand binding site of the peroxisome proliferator activated receptor γ (PPARγ) and results in the inhibition of adipocyte differentiation. It favors cell growth suppression in breast cancer cell lines even in the presence of PPARγ agonist rosiglitazone. It stimulates M2c macrophages differentiation and triggers growth arrest-specific 6 (Gas6) expression. GW9662 co treatment with other PPARγ ligands elicits antiproliferative effects on the glioblastoma stem cells and could be a potent therapeutic agent.
GW9662 is an irreversible PPARγ antagonist. GW9662 inhibits connective tissue growth factor and activation of CD36 by IL-4.
GW9662 is an irreversible PPARγ antagonist; inhibits connective tissue growth factor, and activation of CD36 by IL-4.

Leistungsmerkmale und Vorteile

This compound is featured on the Nuclear Receptors (PPARs) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Rechtliche Hinweise

Sold for research purposes only, under agreement from Glaxo­Smith­Kline

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3


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Xu SC, et al.
PPAR Research, 2017(43), 26303-26313 (2017)
Functional consequences of cysteine modification in the ligand binding sites of peroxisome proliferator activated receptors by GW9662
Leesnitzer LM, et al.
Biochemistry, 41(21), 6640-6650 (2002)
The synergistic enhancement of cloning efficiency in individualized human pluripotent stem cells by peroxisome proliferative-activated receptor-gamma (PPARgamma) activation and rho-associated kinase (ROCK) inhibition
Kajabadi NS, et al.
The Journal of Biological Chemistry, 290(43), 26303-26313 (2015)
GW9662, a potent antagonist of PPARgamma, inhibits growth of breast tumour cells and promotes the anticancer effects of the PPARgamma agonist rosiglitazone, independently of PPARgamma activation
Seargent JM, et al.
British Journal of Pharmacology, 143(8), 933-937 (2004)
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PPARgamma, a member of the peroxisome proliferator-activated receptor family, is overexpressed in prostate cancer. Natural and synthetic ligands of PPARgamma via genomic and nongenomic actions promote cell cycle arrest and apoptosis of several prostate cancer cells, in vitro. Insulin-like growth

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