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MedKoo Cat#: 561776 | Name: TBE-31

Description:

WARNING: This product is for research use only, not for human or veterinary use.

TBE-31 is a highly potent activator of Nrf2. It also acts as a potent phase 2 cytoprotective pathway inducer and liver carcinogenesis blocker.

Chemical Structure

TBE-31
TBE-31
CAS#936475-62-6

Theoretical Analysis

MedKoo Cat#: 561776

Name: TBE-31

CAS#: 936475-62-6

Chemical Formula: C21H18N2O2

Exact Mass: 330.1368

Molecular Weight: 330.38

Elemental Analysis: C, 76.34; H, 5.49; N, 8.48; O, 9.69

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
TBE-31; TBE 31; TBE31;
IUPAC/Chemical 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
InChi Key
ISZIRXMFUSQQOS-NDXORKPFSA-N
InChi Code
InChI=1S/C21H18N2O2/c1-5-21-7-6-16-19(2,3)18(25)14(12-23)9-20(16,4)17(21)8-15(24)13(10-21)11-22/h1,8-10,16H,6-7H2,2-4H3/t16-,20-,21-/m0/s1
SMILES Code
N#CC(C(C=C1[C@@]2(C)C=C3C#N)=O)=C[C@]1(C#C)CC[C@H]2C(C)(C)C3=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 330.38 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Yao W, Zhang JC, Ishima T, Ren Q, Yang C, Dong C, Ma M, Saito A, Honda T, Hashimoto K. Antidepressant effects of TBE-31 and MCE-1, the novel Nrf2 activators, in an inflammation model of depression. Eur J Pharmacol. 2016 Dec 15;793:21-27. doi: 10.1016/j.ejphar.2016.10.037. Epub 2016 Nov 1. PubMed PMID: 27815170. 2: Chan E, Saito A, Honda T, Di Guglielmo GM. The acetylenic tricyclic bis(cyano enone), TBE-31, targets microtubule dynamics and cell polarity in migrating cells. Biochim Biophys Acta. 2016 Apr;1863(4):638-49. doi: 10.1016/j.bbamcr.2016.01.008. Epub 2016 Jan 13. PubMed PMID: 26775215. 3: Kostov RV, Knatko EV, McLaughlin LA, Henderson CJ, Zheng S, Huang JT, Honda T, Dinkova-Kostova AT. 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 Sep 25;465(3):402-7. doi: 10.1016/j.bbrc.2015.08.016. Epub 2015 Aug 8. PubMed PMID: 26265043; PubMed Central PMCID: PMC4567061. 4: Abeti R, Uzun E, Renganathan I, Honda T, Pook MA, Giunti P. Targeting lipid peroxidation and mitochondrial imbalance in Friedreich's ataxia. Pharmacol Res. 2015 Sep;99:344-50. doi: 10.1016/j.phrs.2015.05.015. Epub 2015 Jul 2. PubMed PMID: 26141703. 5: Knatko EV, Ibbotson SH, Zhang Y, Higgins M, Fahey JW, Talalay P, Dawe RS, Ferguson J, Huang JT, Clarke R, Zheng S, Saito A, Kalra S, Benedict AL, Honda T, Proby CM, Dinkova-Kostova AT. Nrf2 Activation Protects against Solar-Simulated Ultraviolet Radiation in Mice and Humans. Cancer Prev Res (Phila). 2015 Jun;8(6):475-86. doi: 10.1158/1940-6207.CAPR-14-0362. Epub 2015 Mar 24. PubMed PMID: 25804610; PubMed Central PMCID: PMC4454593. 6: Zheng S, Huang JT, Knatko EV, Sharp S, Higgins M, Ojima I, Dinkova-Kostova AT, Honda T. Synthesis of (13) C2 (15) N2 -labeled anti-inflammatory and cytoprotective tricyclic bis(cyanoenone) ([(13) C2 (15) N2 ]-TBE-31) as an internal standard for quantification by stable isotope dilution LC-MS method. J Labelled Comp Radiopharm. 2014 Aug;57(10):606-10. doi: 10.1002/jlcr.3230. Epub 2014 Sep 5. PubMed PMID: 25196444. 7: Chan E, Saito A, Honda T, Di Guglielmo GM. The acetylenic tricyclic bis(cyano enone), TBE-31 inhibits non-small cell lung cancer cell migration through direct binding with actin. Cancer Prev Res (Phila). 2014 Jul;7(7):727-37. doi: 10.1158/1940-6207.CAPR-13-0403. Epub 2014 May 7. PubMed PMID: 24806663. 8: Onyango EO, Fu L, Gribble GW. Synthesis of a dicyano abietane, a key intermediate for the anti-inflammatory agent TBE-31. Org Lett. 2014 Jan 3;16(1):322-4. doi: 10.1021/ol403289y. Epub 2013 Dec 4. PubMed PMID: 24303944. 9: Saito A, Higgins M, Zheng S, Li W, Ojima I, Dinkova-Kostova AT, Honda T. Synthesis and biological evaluation of biotin conjugates of (±)-(4bS,8aR,10aS)-10a-ethynyl-4b,8,8-trimethyl-3,7-dioxo-3,4b,7,8,8a,9,10,10a-oc tahydro-phenanthrene-2,6-dicarbonitrile, an activator of the Keap1/Nrf2/ARE pathway, for the isolation of its protein targets. Bioorg Med Chem Lett. 2013 Oct 15;23(20):5540-3. doi: 10.1016/j.bmcl.2013.08.058. Epub 2013 Aug 21. PubMed PMID: 24018193. 10: Zheng S, Resch D, Honda T, Jasinski JP. (±)-(4bS,8aR,10aS)-10a-Ethynyl-4b,8,8-trimethyl-3,7-dioxo-3,4b,7,8,8a,9,10,10a-oc ta-hydro-phenanthrene-2,6-dicarbonitrile. Acta Crystallogr Sect E Struct Rep Online. 2012 Nov 1;68(Pt 11):o3095-6. doi: 10.1107/S1600536812041244. Epub 2012 Oct 10. PubMed PMID: 23284424; PubMed Central PMCID: PMC3515197. 11: Kalra S, Knatko EV, Zhang Y, Honda T, Yamamoto M, Dinkova-Kostova AT. Highly potent activation of Nrf2 by topical tricyclic bis(cyano enone): implications for protection against UV radiation during thiopurine therapy. Cancer Prev Res (Phila). 2012 Jul;5(7):973-81. doi: 10.1158/1940-6207.CAPR-12-0041. Epub 2012 Jun 1. PubMed PMID: 22659146. 12: Zheng S, Santosh Laxmi YR, David E, Dinkova-Kostova AT, Shiavoni KH, Ren Y, Zheng Y, Trevino I, Bumeister R, Ojima I, Wigley WC, Bliska JB, Mierke DF, Honda T. Synthesis, chemical reactivity as Michael acceptors, and biological potency of monocyclic cyanoenones, novel and highly potent anti-inflammatory and cytoprotective agents. J Med Chem. 2012 May 24;55(10):4837-46. doi: 10.1021/jm3003922. Epub 2012 May 7. PubMed PMID: 22533790. 13: Honda T, Yoshizawa H, Sundararajan C, David E, Lajoie MJ, Favaloro FG Jr, Janosik T, Su X, Honda Y, Roebuck BD, Gribble GW. Tricyclic compounds containing nonenolizable cyano enones. A novel class of highly potent anti-inflammatory and cytoprotective agents. J Med Chem. 2011 Mar 24;54(6):1762-78. doi: 10.1021/jm101445p. Epub 2011 Mar 1. PubMed PMID: 21361338; PubMed Central PMCID: PMC3251033. 14: Liby K, Yore MM, Roebuck BD, Baumgartner KJ, Honda T, Sundararajan C, Yoshizawa H, Gribble GW, Williams CR, Risingsong R, Royce DB, Dinkova-Kostova AT, Stephenson KK, Egner PA, Yates MS, Groopman JD, Kensler TW, Sporn MB. A novel acetylenic tricyclic bis-(cyano enone) potently induces phase 2 cytoprotective pathways and blocks liver carcinogenesis induced by aflatoxin. Cancer Res. 2008 Aug 15;68(16):6727-33. doi: 10.1158/0008-5472.CAN-08-1123. PubMed PMID: 18701497; PubMed Central PMCID: PMC3767150.