Troglitazone
Troglitazone is a thiazolidinedione PPARγ agonist that exhibits anti-diabetic, anticancer, anti-fibrotic, and anti-inflammatory activities. Troglitazone contains a vitamin E-like ring structure that forms hepatotoxic metabolites in vivo. Troglitazone induces apoptosis in cervical cancer cells and decreases expression and activity of telomerase in ER- breast cancer cells. In vitro, troglitazone activates AMPK, decreases membrane potential, inhibits high glucose-closed ATP-sensitive K+ channels, and decreases insulin hypersecretion. In alveolar epithelial cells, troglitazone inhibits TGF-β1-induced activation of Akt, GSK-3β and Smad2/3, decreases β-catenin signaling, and suppresses epithelial-to-mesenchymal transition (EMT). Additionally, this compound inhibits PAM-induced increases in TGF-β1 and increases MUC1 expression in airway epithelial cells.
References PubMed ID：:http://www.ncbi.nlm.nih.gov/pubmed/18978475
| Cas No. |
97322-87-7 |
|---|---|
| Purity |
≥97% |
| Formula |
C24H27NO5S |
| Formula Wt. |
441.54 |
| Chemical Name |
5-[[4-[(3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl- 2H-1-benzopyran-2-yl)methoxy]phenyl]methyl]-2,4- thiazolidinedione |
| IUPAC Name |
5-[[4-[(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromen-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione |
| Synonym |
Noscal; Prelay; Rezulin; Romozin |
| Melting Point |
184-186°C |
| Solubility |
Soluble in DMSO 15mg/mL, and dimethyl formide. Slightly soluble in 100% ethanol (warm). |
| Appearance |
Yellow Solid |
Chen HM, Zhang DG, Wu JX, et al. Ubiquitination of p53 is involved in troglitazone induced apoptosis in cervical cancer cells. Asian Pac J Cancer Prev. 2014;15(5):2313-8. PMID: 24716976.
Deng R, Nie A, Jian F, et al. Acute exposure of beta-cells to troglitazone decreases insulin hypersecretion via activating AMPK. Biochim Biophys Acta. 2014 Jan;1840(1):577-85. PMID: 24144566.
Zhou B, Buckley ST, Patel V, et al. Troglitazone attenuates TGF-β1-induced EMT in alveolar epithelial cells via a PPARγ-independent mechanism. PLoS One. 2012;7(6):e38827. PMID: 22745681.
Park YS, Lillehoj EP, Kato K, et al. PPARγ inhibits airway epithelial cell inflammatory response through a MUC1-dependent mechanism. Am J Physiol Lung Cell Mol Physiol. 2012 Apr 1;302(7):L679-87. PMID: 22268120.
Rashid-Kolvear F, Taboski MA, Nguyen J, et al. Troglitazone suppresses telomerase activity independently of PPARgamma in estrogen-receptor negative breast cancer cells. BMC Cancer. 2010 Jul 22;10:390. PMID: 20650001.
Ozaki S, Minamisono T, Yamashita T, et al. Supersaturation-nucleation behavior of poorly soluble drugs and its impact on the oral absorption of drugs in thermodynamically high-energy forms. J Pharm Sci. 2012 Jan;101(1):214-222. PMID: 21918988.
