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CDDO

Item № 81035
CAS № 218600-44-3
Purity ≥95%
product image
                (CAS 218600-44-3)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     1 mg $49.00 0.00
     5 mg $221.00 0.00
     10 mg $392.00 0.00

Pricing updated 2019-07-17. Prices are subject to change without notice.

Description
Synonyms
  • Bardoxolone
  • RTA 401

CDDO is a synthetic oleanane triterpenoid that blocks the cellular synthesis of inducible nitric oxide synthase and inducible COX-2 in INF-γ-activated mouse macrophages with an IC50 value of 0.4 nM.1 By suppressing reactive oxygen and nitrogen species (ROS/RNS) formation, it promotes the cellular control of ROS/RNS levels that would lead to DNA damage associated with tumorigenesis.2 In various cancer cell lines, CDDO has been shown to specifically inhibit proliferation and induce apoptosis.2 Mechanism studies revealed that CDDO is a ligand for peroxisome proliferator-activated receptor γ, and also that it induces genes regulated by Nrf2, including heme oxygenase-1 and eotaxin-1, which play a role in antioxidant response element signaling activity.3,4,5

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Technical Information
Formal Name
2-cyano-3,12-dioxo-oleana-1,9(11)-dien-28-oic acid
CAS Number
218600-44-3
Synonyms
  • Bardoxolone
  • RTA 401
Molecular Formula
C31H41NO4
Formula Weight
491.7
Purity
≥95%
Formulation
A crystalline solid
λmax
240 nm
SMILES
N#CC1=C[C@@]2(C)[C@](CC[C@]([C@@]3(C)[C@@]4([H])C5[C@@](CCC(C)(C)C5)(C(O)=O)CC3)(C)C2=CC4=O)([H])C(C)(C)C1=O
InChI Code
InChI=1S/C31H41NO4/c1-26(2)10-12-31(25(35)36)13-11-30(7)23(19(31)16-26)20(33)14-22-28(5)15-18(17-32)24(34)27(3,4)21(28)8-9-29(22,30)6/h14-15,19,21,23H,8-13,16H2,1-7H3,(H,35,36)/t19?,21-,23-,28-,29+,30+,31?/m0/s1
InChI Key
TXGZJQLMVSIZEI-RPCUOREFSA-N

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
Stability
≥ 2 years
Downloads & Resources
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Additional Information

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References & Product Citations
Product Description References

1. Honda, T., Rounds, B.V., Gribble, G.W., et al. Design and synthesis of 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid, a novel and highly active inhibitor of nitric oxide production in mouse macrophages Bioorganic & Medicinal Chemistry Letters 8, 2711-2714 (1998).

2. Suh, N., Wang, Y., Honda, T., et al. A novel synthetic oleanane triterpenoid, 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid, with potent differentiating, antiproliferative, and anti-inflammatory activity Cancer Research 59, 336-341 (1999).

3. Ferguson, H.E., Kulkarni, A., Lehmann, G.M., et al. Electrophilic peroxisome proliferator-activated receptor-γ ligands have potent antifibrotic effects in human lung fibroblasts American Journal of Respiration, Cell, and Molecular Biology 41, 722-730 (2009).

4. 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 Research 65, 4789-4798 (2005).

5. Fourtounis, J., Wang, I.M., Mathieu, M.C., et al. Gene expression profiling following NRF2 and KEAP1 siRNA knockdown in human lung fibroblasts identifies CCL11/Eotaxin-1 as a novel NRF2 regulated gene Respiratory Research 13(1), (2012).

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