All Photos(1)

5.05308

Sigma-Aldrich

CDDO-Me - CAS 218600-53-4 - Calbiochem

Synonym(s):
CDDO-Me - CAS 218600-53-4 - Calbiochem, Methyl-2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oate, Bardoxolone methyl, BARD, NSC 713200, Nrf Activator V
Empirical Formula (Hill Notation):
C32H43NO4
CAS Number:
Molecular Weight:
505.69
MDL number:

Quality Level

assay

≥98% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

white

solubility

DMSO: 50 mg/mL

storage temp.

2-8°C

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

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

Warning

Toxicity: Standard Handling (A)

Reconstitution

Use only fresh DMSO for reconstitution.
Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

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.

Legal Information

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

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