936475-62-6
Chemical Structure
TBE 31
- CAS No.: 936475-62-6
- Formula:C21H18N2O2
- Molecular Weight:330.38
IUPAC Name: (4bS,8aR,10aS)-10a-ethynyl-4b,8,8-trimethyl-3,7-dioxo-3,4b,7,8,8a,9,10,10a-octahydrophenanthrene-2,6-dicarbonitrile
InChIKey: ISZIRXMFUSQQOS-NDXORKPFSA-N
SMILES: C#C[C@]12C([C@@]3([C@@](C(C)(C(C(C#N)=C3)=O)C)([H])CC1)C)=CC(C(C#N)=C2)=O
Biological Activity: TBE 31 is an orally active Keap1/Nrf2 pathway activator and NQO1 inducer with a Dm value of 1.1 nM for NQO1. TBE 31 binds to cysteine residues of Keap1, inhibits ubiquitination and degradation of Nrf2, thereby activating the expression of ARE-dependent genes. TBE 31 induces cytoprotective enzymes including NQO1 and GST isoforms, promotes Nrf2 accumulation, and upregulates Nrf2-regulated genes related to antioxidation and lipid metabolism. TBE 31 inhibits pro-inflammatory responses, formation of AFB1-DNA adducts, endoplasmic reticulum stress, cell apoptosis (apoptosis), hepatic fibrosis, oxidative stress, and the expression of ChREBP. TBE 31 reduces the number of tumors in a mouse model of ultraviolet-induced skin carcinogenesis. TBE 31 enhances nerve growth factor-induced neurite outgrowth. TBE 31 attenuates LPS-induced serum TNF-α levels and immobility time in mice. TBE 31 can be used in research related to liver cancer, skin cancer, inflammation-related depression, and non-alcoholic steatohepatitis[1][2][3][4][5].
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TBE 31 | TBE 31 is an orally active Keap1/Nrf2 pathway activator and NQO1 inducer with a Dm value of 1.1 nM for NQO1. TBE 31 binds to cysteine residues of Keap1, inhibits ubiquitination and degradation of Nrf2, thereby activating the expression of ARE-dependent genes. TBE 31 induces cytoprotective enzymes including NQO1 and GST isoforms, promotes Nrf2 accumulation, and upregulates Nrf2-regulated genes related to antioxidation and lipid metabolism. TBE 31 inhibits pro-inflammatory responses, formation of AFB1-DNA adducts, endoplasmic reticulum stress, cell apoptosis (apoptosis), hepatic fibrosis, oxidative stress, and the expression of ChREBP. TBE 31 reduces the number of tumors in a mouse model of ultraviolet-induced skin carcinogenesis. TBE 31 enhances nerve growth factor-induced neurite outgrowth. TBE 31 attenuates LPS-induced serum TNF-α levels and immobility time in mice. TBE 31 can be used in research related to liver cancer, skin cancer, inflammation-related depression, and non-alcoholic steatohepatitis. | |||||||||||||||||||||
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References
- [1]. Dinkova-Kostova AT, et al. An exceptionally potent inducer of cytoprotective enzymes: elucidation of the structural features that determine inducer potency and reactivity with Keap1. J Biol Chem. 2010;285(44):33747-33755. [Content Brief]
- [2]. Kostov RV, et al. Pharmacokinetics and pharmacodynamics of orally administered acetylenic tricyclic bis(cyanoenone), a highly potent Nrf2 activator with a reversible covalent mode of action. Biochem Biophys Res Commun. 2015;465(3):402-407. [Content Brief]
- [3]. Yao W, et al. Antidepressant effects of TBE-31 and MCE-1, the novel Nrf2 activators, in an inflammation model of depression. Eur J Pharmacol. 2016;793:21-27. [Content Brief]
- [4]. Sharma RS, et al. Experimental Nonalcoholic Steatohepatitis and Liver Fibrosis Are Ameliorated by Pharmacologic Activation of Nrf2 (NF-E2 p45-Related Factor 2). Cell Mol Gastroenterol Hepatol. 2017;5(3):367-398. Published 2017 Dec 13. [Content Brief]
- [5]. Onyango EO, et al. Synthesis of a dicyano abietane, a key intermediate for the anti-inflammatory agent TBE-31. Org Lett. 2014;16(1):322-324. [Content Brief]
