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5.05308

Sigma-Aldrich

CDDO-Me

Synonym(s):

CDDO-Me, Methyl-2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oate, Bardoxolone methyl, BARD, NSC 713200, Nrf Activator V

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About This Item

Empirical Formula (Hill Notation):
C32H43NO4
CAS Number:
218600-53-4
Molecular Weight:
505.69
MDL number:
MFCD11983137
UNSPSC Code:
12352200

Assay

≥98% (HPLC)

Quality Level

100

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

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.

Legal Information

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

Disclaimer

Toxicity: Standard Handling (A)

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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