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GW 9662

Cayman Chemical Item Number 70785

(CAS 22978-25-2)

GW 9662 (CAS 22978-25-2)

See more	Nuclear Receptors (94) PPAR (59) Receptor Antagonist (94) Atherosclerosis (325) Endocrinology (337) Metabolism (145)

Description

The peroxisome proliferator-activated receptor γ (PPARγ) is the nuclear receptor responsible for transducing the therapeutic activity of the thiazolidinediones. Thiazolidinediones are a group of structurally related synthetic PPARγ agonists with antidiabetic actions in vivo.^1,2 Rosiglitazone (BRL 49653) is a prototypical thiazolidinedione and has served as a reference compound for this class.³ There are many PPARγ agonists, including 15-deoxy-Δ^12,14-prostaglandin J₂ and azelaoyl PAF, which are naturally derived.^4,5 However, only a few antagonists have been reported.⁶ GW 9662 blocks the PPARγ-induced differentiation of monocytes to osteoclasts by >90% at a dose of 0.1 µM.⁶ It is therefore a much more potent antagonist than BADGE, which is another reported PPARγ antagonist.⁷

1 Willson, T.M., Cobb, J.E., Cowan, D.J., et al. The structure-activity relationship between peroxisome proliferator-activated receptor γ agonism and the antihyperglycemic activity of thiazolidinediones. J Med Chem 39 665-668 (1996).

2 Maxey, K.M., Hessler, E., MacDonald, J., et al. The nature and composition of 15-deoxy-Δ^12,14-PGJ₂. Prostaglandins Other Lipid Mediat 62 15-21 (2000).

3 Wright, H.M., Clish, C.B., Mikami, T., et al. A synthetic antagonist for the peroxisome proliferator-activated receptor γ inhibits adipocyte differentiation. J Biol Chem 275 1873-1877 (2000).

4 Lehmann, J.M., Moore, L.B., Smith-Oliver, T.A., et al. An antidiabetic thiazolidinedione is a high affinity ligand for peroxisome proliferator-activated receptor γ (PPARγ). J Biol Chem 270 12953-12956 (1995).

5 Cantello, B.C.C., Cawthorne, M.A., Cottam, G.P., et al. [[ω-(Heterocyclylamino)alkoxy]benzyl]-2,4-thiazolidinediones as potent antihyperglycemic agents. J Med Chem 37 3977-3985 (1994).

6 Davies, S.S., Pontsler, A.V., Marathe, G.K., et al. Oxidized alkyl phospholipids are specific, high affinity peroxisome proliferator-activated receptor γ ligands and agonists. J Biol Chem 276 16015-16023 (2001).

7 Bendixen, A.C., Shevde, N.K., Dienger, K.M., et al. IL-4 inhibits osteoclast formation through a direct action on osteoclast precursors via peroxisome proliferator-activated receptor γ1. Proc Natl Acad Sci USA 98 2443-2448 (2001).

Formal Name	2-chloro-5-nitrobenzanilide
CAS Number	22978-25-2
Molecular Formula	C₁₃H₉ClN₂O₃
Formula Weight	276.7
Formulation	A crystalline solid
Purity	≥98%
λ_max	261 nm
Stability	2 years
Storage	-20°C
Shipping	Room temperature in continental US; may vary elsewhere
SMILES	Copy SMILES to clipboard O=C(C1=CC([N+]([O-])=O)=CC=C1Cl)N([H])C2=CC=CC=C2

Background Reading

Willson, T.M., Cobb, J.E., Cowan, D.J., et al. The structure-activity relationship between peroxisome proliferator-activated receptor γ agonism and the antihyperglycemic activity of thiazolidinediones. J Med Chem 39 665-668 (1996).

Maxey, K.M., Hessler, E., MacDonald, J., et al. The nature and composition of 15-deoxy-Δ^12,14-PGJ₂. Prostaglandins Other Lipid Mediat 62 15-21 (2000).

Wright, H.M., Clish, C.B., Mikami, T., et al. A synthetic antagonist for the peroxisome proliferator-activated receptor γ inhibits adipocyte differentiation. J Biol Chem 275 1873-1877 (2000).

Lehmann, J.M., Moore, L.B., Smith-Oliver, T.A., et al. An antidiabetic thiazolidinedione is a high affinity ligand for peroxisome proliferator-activated receptor γ (PPARγ). J Biol Chem 270 12953-12956 (1995).

Cantello, B.C.C., Cawthorne, M.A., Cottam, G.P., et al. [[ω-(Heterocyclylamino)alkoxy]benzyl]-2,4-thiazolidinediones as potent antihyperglycemic agents. J Med Chem 37 3977-3985 (1994).

Davies, S.S., Pontsler, A.V., Marathe, G.K., et al. Oxidized alkyl phospholipids are specific, high affinity peroxisome proliferator-activated receptor γ ligands and agonists. J Biol Chem 276 16015-16023 (2001).

Bendixen, A.C., Shevde, N.K., Dienger, K.M., et al. IL-4 inhibits osteoclast formation through a direct action on osteoclast precursors via peroxisome proliferator-activated receptor γ1. Proc Natl Acad Sci USA 98 2443-2448 (2001).

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GW 9662 is available in the following screening library:

Bio-active Lipid I Screening Library (96-Well)

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Related Products

15-deoxy-Δ^12,14-Prostaglandin J₂

BADGE

Rosiglitazone (potassium salt)

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