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Safety Information

M6191

Sigma-Aldrich

GW9662

>98% (HPLC)

Synonym(s):

2-Chloro-5-nitro-N-phenylbenzamide

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About This Item

Empirical Formula (Hill Notation):
C13H9ClN2O3
CAS Number:
22978-25-2
Molecular Weight:
276.68
MDL number:
MFCD01215270
UNSPSC Code:
51111800
PubChem Substance ID:
24278560
NACRES:
NA.77

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.

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.

Legal Information

Sold for research purposes only, under agreement from Glaxo­Smith­Kline

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

M6191-25MG:
M6191-5MG:
M6191-VAR:
M6191-BULK:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Bezafibrate attenuates pressure overload-induced cardiac hypertrophy and fibrosis
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)
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
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