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CDDO-TFEA (Synonyms: CDDO-Trifluoethyl Amide,RTA 404,TP-500)

Catalog No.GC16625

Nrf2 activator

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CDDO-TFEA Chemical Structure

Cas No.: 932730-52-4

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Sample solution is provided at 25 µL, 10mM.

Product Documents

Quality Control & SDS

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Background

CDDO-trifluoroethyl-amide (CDDO-TFEA), a trifluoroethylamide derivative of CDDO, is an Nrf2/ARE pathway activator [1][2][3].

The NF-E2-related factor-2 (Nrf2)/antioxidant response element (ARE) signaling pathway is an important pathway involved in antioxidant and anti-inflammatory responses. Modulation of the Nrf2/ARE pathway is an attractive therapeutic target for neurodegenerative diseases such as amyotrophic lateral sclerosis (ALS) and Huntington's disease (HD) [2][3].

CDDO-TFEA is an Nrf2/ARE pathway activator. In NSC-34 G93A SOD1 cells, CDDO-TFEA upregulated Nrf2 expression and caused translocation of Nrf2 into the nucleus. CDDO-TFEA also increased the expression of Nrf2/ARE-regulated proteins (NQO-1, HO-1 and Glutathione reductase).

In mice with experimental autoimmune encephalomyelitis (EAE), CDDO-TFEA reduced immune and inflammatory cell populations. CDDO-TFEA also significantly reduced Th1 and Th17 cytokines (IL6, IL17, IFNγ, TNFα and GMCSF) [1]. In ALS mice model, CDDO-TFEA upregulated the expression and resulted in translocation of Nrf2 to the nucleus of neurons in the spinal cord. In G93A SOD1 mice, CDDO-TFEA increased the life-span by 17.6 days [2].

References:
[1].  Pareek TK, Belkadi A, Kesavapany S, et al. Triterpenoid modulation of IL-17 and Nrf-2 expression ameliorates neuroinflammation and promotes remyelination in autoimmune encephalomyelitis. Sci Rep. 2011;1:201.
[2].  Neymotin A, Calingasan NY, Wille E, et al. Neuroprotective effect of Nrf2/ARE activators, CDDO ethylamide and CDDO trifluoroethylamide, in a mouse model of amyotrophic lateral sclerosis. Free Radic Biol Med. 2011 Jul 1;51(1):88-96.
[3].  Stack C, Ho D, Wille E, et al. Triterpenoids CDDO-ethyl amide and CDDO-trifluoroethyl amide improve the behavioral phenotype and brain pathology in a transgenic mouse model of Huntington's disease. Free Radic Biol Med. 2010 Jul 15;49(2):147-58.

Chemical Properties

Cas No. 932730-52-4 SDF
Synonyms CDDO-Trifluoethyl Amide,RTA 404,TP-500
Chemical Name 2-cyano-3,12-dioxo-N-(2,2,2-trifluoroethyl)-oleana-1,9(11)-dien-28-amide
Canonical SMILES CC1(CC[C@@]2(CC[C@@](C)([C@@]3(CC[C@]4(C(C)(C(C(C#N)=C[C@@]4(C3=CC5=O)C)=O)C)[H])C)[C@]5([C@@]2(C1)[H])[H])C(NCC(F)(F)F)=O)C
Formula C33H43F3N2O3 M.Wt 572.7
Solubility ≤5mg/ml in ethanol;5mg/ml in DMSO;5mg/ml in dimethyl formamide Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table

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1 mg 5 mg 10 mg
1 mM 1.7461 mL 8.7306 mL 17.4611 mL
5 mM 0.3492 mL 1.7461 mL 3.4922 mL
10 mM 0.1746 mL 0.8731 mL 1.7461 mL
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