form
solid
InChI
1S/C32H43NO4/c1-27(2)11-13-32(26(36)37-8)14-12-31(7)24(20(32)17-27)21(34)15-23-29(5)16-19(18-33)25(35)28(3,4)22(29)9-10-30(23,31)6/h15-16,20,22,24H,9-14,17H2,1-8H3/t20-,22-,24-,29-,30+,31+,32-/m0/s1
InChI key
WPTTVJLTNAWYAO-KPOXMGGZSA-N
assay
≥98% (HPLC)
manufacturer/tradename
Calbiochem®
storage condition
OK to freeze, protect from light
color
white
solubility
DMSO: 50 mg/mL
Quality Level
General description
A cell-permeable, bioavailable synthetic oleanane triterpenoid compound with anti-inflammatory, anti-tumor and cytoprotective properties. Shown to significantly reduce the expression of several inflammatory mediators, including IL-6, IL-10, IL-12, TNFα, Mip1α and others. Reverses high fat diet-induced type 2 diabetes in C57BL/6 mice (3 mg/kg) and improves glucose homeostasis and insulin sensitivity. Down-regulates lipogenic gene expression in hepatocytes. Exhibits anti-proliferative activity in osteosarcoma cells (IC50 = 800, 150, 330, and 170 nM in HOB-c, KHOS, KHOSR2, and U2OS cells, respectively). Enhances the effectiveness of chemotherapeutic agents by inducing intrinsic mitochondrial-dependent apoptotic pathway. Reported to interact with multi cellular targets, namely, Nrf2-Keap1, IKK, JAK-STAT, PPARγ, ErbB2, PTEN, mTOR and Arp3 and covalently modify active site Cys residue via Michael addition.
Biochem/physiol Actions
Cell permeable: yes
Reversible: no
Preparation Note
Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.
Use only fresh DMSO for reconstitution.
Other Notes
Liby, K.T. and Sporn, M.B., 2012. Pharmacol. Rev.64, 972.
Saha, P.K. et al. 2010. J. Biol. Chem.285, 40581.
Ryu, K., et al. 2010. BMC Cancer10, 187.
Liby, K.T., et al. 2007. Nat. Rev. Cancer7, 357.
Shishodia S., et al. 2006. Clin. Cancer Res.12, 1828.
Zou, W., et al. 2004. Cancer Res.64, 7570.
Kim, Y., et al. 2002. J. Biol. Chem.277, 22320.
Konopleva, M., et al. 2002. Blood99, 326.
Wang, Y., et al. 2000. Mol Endocrinol.14, 1550.
Saha, P.K. et al. 2010. J. Biol. Chem.285, 40581.
Ryu, K., et al. 2010. BMC Cancer10, 187.
Liby, K.T., et al. 2007. Nat. Rev. Cancer7, 357.
Shishodia S., et al. 2006. Clin. Cancer Res.12, 1828.
Zou, W., et al. 2004. Cancer Res.64, 7570.
Kim, Y., et al. 2002. J. Biol. Chem.277, 22320.
Konopleva, M., et al. 2002. Blood99, 326.
Wang, Y., et al. 2000. Mol Endocrinol.14, 1550.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Disclaimer
Toxicity: Standard Handling (A)
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_c
Not applicable
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