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GW 9662

Item № 70785
CAS № 22978-25-2
Purity ≥98%
product image
                (CAS 22978-25-2)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     1 mg $8.00 0.00
     5 mg $36.00 0.00
     10 mg $64.00 0.00
     50 mg $280.00 0.00

Pricing updated 2019-07-23. Prices are subject to change without notice.

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-Δ12,14-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

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Technical Information
Formal Name
2-chloro-5-nitrobenzanilide
CAS Number
22978-25-2
Molecular Formula
C13H9ClN2O3
Formula Weight
276.7
Purity
≥98%
Formulation
A crystalline solid
λmax
261 nm
SMILES
O=C(C1=CC([N+]([O-])=O)=CC=C1Cl)N([H])C2=CC=CC=C2
InChI Code
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
Origin
  • Synthetic

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Stability
≥ 2 years
Downloads & Resources
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Additional Information

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References & Product Citations
Product Description References

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-Δ12,14-PGJ2 Prostaglandins & Other Lipid Mediators 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 The Journal of Biological Chemisty 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(22), 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 The Journal of Biological Chemisty 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 Proceedings of the National Academy of Sciences of the United States of America 98, 2443-2448 (2001).

Product Citations

McDougle, D.R., Watson, J.E., Abdeen, A.A., et al. Anti-inflammatory ω-3 endocannabinoid epoxides Proc. Natl. Acad. Sci. U.S.A. 114(30), E6034-E6043 (2017).

Bain, G., Shannon, K.E., Huang, F., et al. Selective Inhibition of Autotaxin Is Efficacious in Mouse Models of Liver Fibrosis J. Pharmacol. Exp. Ther. 360(1), 1-13 (2016).

Change, Y.-C., Chen, Y.-J., Huang, C.-W., et al. Cyclic stretch facilitates myogenesis in C2C12 myoblasts and rescues thiazolidinedione-inhibited myotube formation Front. Bioeng. Biotechnol. 4(27), (2016).

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