648469-M

Troglitazone

A α-tocopherol (vitamin E) moiety containing thiazolidinedione class of insulin-sensitizer that acts as an activator of peroxisome proliferator-activated receptors γ (PPARγ).

• Synonym(s): Troglitazone
• Empirical Formula (Hill Notation): C₂₄H₂₇NO₅S
• CAS Number: 97322-87-7
• Molecular Weight: 441.54
• UNSPSC Code: 12352200

Properties

• Quality Level: 100
• assay: ≥98% (HPLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; protect from light
• color: white to yellow
• solubility: DMSO: 10 mg/mL; ethanol: 5 mg/mL
• storage temp.: −20°C
• InChI: 1S/C24H27NO5S/c1-13-14(2)21-18(15(3)20(13)26)9-10-24(4,30-21)12-29-17-7-5-16(6-8-17)11-19-22(27)25-23(28)31-19/h5-8,19,26H,9-12H2,1-4H3,(H,25,27,28)
• InChI key: GXPHKUHSUJUWKP-UHFFFAOYSA-N

Description

General description

A α-tocopherol (vitamin E) moiety containing thiazolidinedione class of insulin-sensitizer that acts as an activator of peroxisome proliferator-activated receptors γ (PPARγ). Also exhibits anti-proliferative and anti-inflammatory properties. Shown to induce cell cycle arrest and apoptosis in human hepatoma cells. Inhibits vascular smooth muscle cell (VSMC) migration by rapidly activating MEK/ERK pathway leading to the induction of c-fos and Ets-1 expression. Blocks PDGF-induced cell proliferation of pancreatic stellate and accelerates p21^Cip1 turnover by inhibiting PKC_δ signaling in VSMCs. Exerts positive inotropic effect via Ca²⁺ sensitization in the sarcoplasmic reticulum and inhibits Na⁺/H⁺ exchange activity and proliferation of macrovascular endothelial cells.

A α-tocopherol (vitamin E) moiety containing thiazolidinedione class of insulin-sensitizer that acts as an activator of peroxisome proliferator-activated receptors γ (PPARγ). Also exhibits anti-proliferative and anti-inflammatory properties. Shown to induce cell cycle arrest and apoptosis in human hepatoma cells. Inhibits vascular smooth muscle cell (VSMCs) migration by rapidly activating MEK/ERK pathway leading to the induction of c-fos and Ets-1 expression. Blocks PDGF-induced cell proliferation of pancreatic stellate and accelerates p21^cip1 turnover by inhibiting PKCδ signaling in VSMCs. Exerts positive inotropic effect via Ca²⁺ sensitization in sarcoplasmic reticulum and inhibits Na⁺/H⁺ change activity.

Biochem/physiol Actions

Primary Target
Peroxisome proliferator-activated receptors γ (PPARγ)

Warning

Toxicity: Standard Handling (A)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). DMSO stock solutions are stable for up to 6 months at -20°C. Ethanol stock solutions are stable for up to 3 months at -20°C.

Other Notes

Masamune, A., et al. 2002. J. Biol. Chem.277, 141.
Boyault, S., et al. 2001. FEBS Lett.501, 24.
de Dios, S.T., et al. 2001. J. Diabetes Complications15, 120.
Furuse, Y., et al. 2001. Br. J. Pharmacol.133, 1307.
Ghanim, H., et al. 2001. J. Clin. Endocrinol. Metab.86, 1306.
Goetze, S., et al. 2001. J. Cardiovasc. Pharmacol.38, 909.
Koga, H., et al. 2001. Hepatology33, 1087.
Rosen, E.D. and Spiegelman, B.M., 2001. J. Biol. Chem.276, 37731.
Subbaramaiah, K., et al. 2001. J. Biol. Chem.276, 12440.
Takashima, T., et al. 2001. Int. J. Oncol.19, 465.
Takeda, K., et al. 2001. J. Biol. Chem.276, 48950.
Tanaka, T., et al. 2001. Cancer Res.61, 2424.
Wakino, S., et al. 2001. J. Biol. Chem.276, 47650.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 2
• flash_point_f: Not applicable
• flash_point_c: Not applicable