M6191

Sigma-Aldrich

GW9662

>98% (HPLC)

Synonym(s):
2-Chloro-5-nitro-N-phenylbenzamide
Empirical Formula (Hill Notation):
C13H9ClN2O3
CAS Number:
Molecular Weight:
276.68
MDL number:
PubChem Substance ID:
NACRES:
NA.77
Pricing and availability is not currently available.

assay

>98% (HPLC)

form

powder

color

white

solubility

DMSO: 26 mg/mL
H2O: insoluble

storage temp.

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)

InChI key

DNTSIBUQMRRYIU-UHFFFAOYSA-N

Gene Information

human ... PPARG(5468)

Application

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.

Packaging

5, 25 mg in glass bottle

Biochem/physiol Actions

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.

Features and Benefits

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.
This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

Sold for research purposes only, under agreement from Glaxo­Smith­Kline
LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Efstathia Papageorgiou et al.
Molecular medicine (Cambridge, Mass.), 14(7-8), 403-411 (2008-05-14)
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...
The PPAR-gamma antagonist GW9662 elicits differentiation of M2c-like cells and upregulation of the MerTK/Gas6 axis: a key role for PPAR-gamma in human macrophage polarization
Zizzo G and Cohen PL
Journal of Inflammation, 12(1), 36-36 (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)
Combination Treatment with PPARgamma Ligand and Its Specific Inhibitor GW9662 Downregulates BIS and 14-3-3 Gamma, Inhibiting Stem-Like Properties in Glioblastoma Cells
Im CN
BioMed Research International, 2017(1), 36-36 (2017)
Bezafibrate attenuates pressure overload-induced cardiac hypertrophy and fibrosis
Xu SC, et al.
PPAR Research, 2017(43), 26303-26313 (2017)

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