An activator of Nrf2 signaling
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CDDO-Im

Item No. 31763

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-(2-cyano-3,12,28-trioxooleana-1,9(11)-dien-28-yl)-1H-imidazole
CAS Number
443104-02-7
Synonyms
  • CDDO-Imidazolide
  • RTA 403
Molecular Formula
C34H43N3O3
Formula Weight
541.7
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 1 mg/mlDMSO: 1 mg/ml
λmax
243 nm
SMILES
O=C(N1C=CN=C1)[C@]23[C@](CC(C)(CC3)C)([H])[C@]4([H])[C@@](CC2)([C@]5(C([C@@]6([C@@](C(C)(C(C(C#N)=C6)=O)C)([H])CC5)C)=CC4=O)C)C
InChi Code
InChI=1S/C34H43N3O3/c1-29(2)10-12-34(28(40)37-15-14-36-20-37)13-11-33(7)26(22(34)18-29)23(38)16-25-31(5)17-21(19-35)27(39)30(3,4)24(31)8-9-32(25,33)6/h14-17,20,22,24,26H,8-13,18H2,1-7H3/t22-,24-,26-,31-,32+,33+,34-/m0/s1
InChi Key
ITFBYYCNYVFPKD-FMIDTUQUSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    CDDO-Im is a synthetic triterpenoid and an activator of Nrf2 signaling.1,2 It binds to Keap1, inhibiting the degradation of Nrf2 and leading to increased Nrf2 protein levels.2 CDDO-Im (100 nM) increases the expression of Nrf2 target genes and activates heme oxygenase-1 (HO-1) in a reporter assay using CV-1 cells.1 It also binds to PPARγ and PPARα (Kis = 344 and 232 nM, respectively) and induces PPARγ transactivation in SW480 cells.3,4 It inhibits the production of nitric oxide synthase (NOS) in isolated mouse macrophages (IC50 = 0.014 nM).5 CDDO-Im (300 nM) inhibits proliferation of U937 and MCF-7 cells and reduces fatty acid synthesis in LiSa-2 human liposarcoma cells when used at a concentration of 100 nM.3,6 It reduces tumor growth in a B16 murine melanoma model when administered at a dose of 50 µg/animal twice per day.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Liby, K., Hock, T., Yore, M.M., et al. The synthetic triterpenoids, CDDO and CDDO-imidazolide, are potent inducers of heme oxygenase-1 and Nrf2/ARE signaling. Cancer Res. 65(11), 4789-4798 (2005).

    2. Meng, X., Waddington, J.C., Tailor, A., et al. CDDO-imidazolide targets multiple amino acid residues on the Nrf2 adaptor, Keap1. J. Med. Chem. 63(17), 9965-9976 (2020).

    3. Place, A.E., Suh, N., Williams, C.R., et al. The novel synthetic triterpenoid, CDDO-imidazolide, inhibits inflammatory response and tumor growth in vivo. Clin. Cancer Res. 9(7), 2798-2806 (2003).

    4. Chintharlapalli, S., Papineni, S., Konopleva, M., et al. 2-Cyano-3,12-dioxoolean-1,9-dien-28-oic acid and related compounds inhibit growth of colon cancer cells through peroxisome proliferator-activated receptor γ-dependent and -independent pathways. Mol. Pharmacol. 68(1), 119-128 (2005).

    5. Honda, T., Honda, Y., Favaloro, F.G., Jr., et al. A novel dicyanotriterpenoid, 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-onitrile, active at picomolar concentrations for inhibition of nitric oxide production. Bioorg. Med. Chem. Lett. 12(7), 1027-1030 (2002).

    6. Hughes, D.T., Martel, P.M., Knlaw, W.B., et al. The synthetic triterpenoid CDDO-Im inhibits fatty acid synthase expression and has antiproliferative and proapoptotic effects in human liposarcoma cells. Cancer Invest. 26(2), 118-127 (2009).