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Troglitazone

Cayman Chemical Item Number 71750

Resulin™ (CAS 97322-87-7)

Troglitazone (CAS 97322-87-7)

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Description

Troglitazone is a TZD which was approved for the treatment of insulin resistance and hyperglycemia in Type II diabetes, under the trade name Resulin™, but was withdrawn from the market due to hepatotoxicity. Troglitazone is a potent and selective PPARγ agonist. The EC50 values for transactivation of human and mouse PPARγ in a cell-based assay are 0.55 and 0.78 µM, respectively.1 In the same assay system, no activation of PPARα and PPARδ was observed at concentrations up to 10 µM. Troglitazone binds to the PPARγ ligand-binding domain (LBD) but fails to induce interaction of the PPARγ LBD with the transcriptional coactivators SRC-1, TIF2, AIB1, p300, or TRAP220.2 Troglitazone also induces cell cycle arrest and apoptosis in several cancer cell lines with an EC50 of 10 µM.3

1 Willson, T.M., Brown, P.J., Sternbach, D.D., et al. The PPARs: From orphan receptors to drug discovery. J Med Chem 43(4) 528-550 (2000).

2 Kodera, Y., Takeyama, K., Murayama, A., et al. Ligand type-specific interactions of peroxisome proliferator-activated receptor γ with transcriptional coactivators. J Biol Chem 275 33201-33204 (2000).

3 Yoshizawa, K., Cioca, D.P., Kawa, S., et al. Peroxisome proliferator-activated receptor γ ligand troglitazone induces cell cycle arrest and apoptosis of hepatocellular carcinoma cell lines. Cancer 95(10) 2243-2251 (2002).

Synonyms
  • ResulinTM
Formal Name 5-​[[4-​[(3,​4-​dihydro-​6-​hydroxy-​2,​5,​7,​8-​tetramethyl-​2H-​1-​benzopyran-​2-​yl)methoxy]phenyl]methyl]-​2,​4-​thiazlidinedione
CAS Number 97322-87-7
Molecular Formula C24H27NO5S
Formula Weight 441.5
Formulation A crystalline solid
Purity >98%
λmax 225, 284 nm
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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O=C1NC(=O)​C(S1)​Cc1ccc(cc1)​OCC1(C)​CCc2c(O1)​c(C)​c(C)​c(O)​c2C

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).

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).

Kodera, Y., Takeyama, K., Murayama, A., et al. Ligand type-specific interactions of peroxisome proliferator-activated receptor γ with transcriptional coactivators. J Biol Chem 275 33201-33204 (2000).

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).

Tchoukalova, Y.D., Hausman, D.B., Dean, R.G., et al. Enhancing effect of troglitazone on porcine adipocyte differentiation in primary culture: a comparison with dexamethasone. Obes Res 8(9) 664-672 (2000).

Yoshizawa, K., Cioca, D.P., Kawa, S., et al. Peroxisome proliferator-activated receptor γ ligand troglitazone induces cell cycle arrest and apoptosis of hepatocellular carcinoma cell lines. Cancer 95(10) 2243-2251 (2002).

Willson, T.M., Brown, P.J., Sternbach, D.D., et al. The PPARs: From orphan receptors to drug discovery. J Med Chem 43(4) 528-550 (2000).

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