BAY 11-7082
featured

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

MedKoo CAT#: 522392

CAS#: 19542-67-7

Description: BAY 11-7082 is an inhibitor of κB kinase (IKK) that has pharmacological activities that include anticancer, neuroprotective, and anti-inflammatory effects. BAY 11-7082 strongly suppressed the production of nitric oxide, prostaglandin E(2), and tumor necrosis factor-α and reduced the translocation of p65, major subunit of nuclear factor-κB, and its upstream signaling events such as phosphorylation of IκBα, IKK, and Akt. In addition. Bay 11-7082 induces cell death independent from inhibition of activation of NFκB transcription factors.BAY 11-7082 suppresses the MyD88-dependent signalling network by targeting the ubiquitin system. Bay 11-7082 induces cell death independent from inhibition of activation of NFκB transcription factors.

Chemical Structure

img
BAY 11-7082
CAS# 19542-67-7
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 522392
Name: BAY 11-7082
CAS#: 19542-67-7
Chemical Formula: C10H9NO2S
Exact Mass: 207.04
Molecular Weight: 207.250
Elemental Analysis: C, 57.96; H, 4.38; N, 6.76; O, 15.44; S, 15.47

Price and Availability

Size Price Availability Quantity
10mg USD 90 Ready to ship
100mg USD 150 Ready to ship
200mg USD 250 Ready to ship
500mg USD 550 Ready to ship
1g USD 950 Ready to ship
2g USD 1650 Ready to ship
5g USD 3250 Ready to ship
Bulk inquiry

Synonym: BAY 11-7082; BAY11-7082; BAY-11-7082; BAY 117082; BAY117082; BAY-117082.

IUPAC/Chemical Name: (2E)-3-[(4-Methylphenyl)sulfonyl]-2-propenenitrile

InChi Key: DOEWDSDBFRHVAP-KRXBUXKQSA-N

InChi Code: InChI=1S/C10H9NO2S/c1-9-3-5-10(6-4-9)14(12,13)8-2-7-11/h2-6,8H,1H3/b8-2+

SMILES Code: N#C/C=C/S(=O)(C1=CC=C(C)C=C1)=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, not in water

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:

Biological target: BAY 11-7082 is an IκBα phosphorylation and NF-κB inhibitor that selectively and irreversibly inhibits the TNF-α-induced phosphorylation of IκB-α and also inhibits ubiquitin-specific protease USP7 and USP21 (IC50=0.19, 0.96 μM, respectively).
In vitro activity: It was found that BAY 11-7082 did not inhibit IKKα, IKKβ and the IKK-related kinases TBK1 and IKK∊ when assayed at 10 μM in vitro (Supplementary Table S1 at http://www.biochemj.org/bj/451/bj4510427add.htm). Nevertheless, BAY 11-7082 completely suppressed the LPS-stimulated (Figure 2A) and IL-1-stimulated (Figure 2B) phosphorylation of the activation loop of IKKβ. As a consequence, the phosphorylation of its substrate p105/NF-κB1 and the degradation of IκBα (which is triggered by the IKK-catalysed phosphorylation of IκBα) were also prevented. The protein kinase TAK1 was partially inhibited by BAY 11-7082 in vitro (Supplementary Table S1), but BAY 11-7082 also suppressed the IL-1-stimulated activation of TBK1 in IL-1R cells (Figure 2C), which is dependent upon the expression of TRAF6, but independent of the expression or catalytic activity of TAK1 [22]. BAY 11-7082 additionally prevented the LPS- or IL-1-stimulated activation of JNK in RAW or IL-1R cells. BAY 11-7082 did not inhibit IRAK4 or IRAK1 in vitro (Supplementary Table S1), which are the most ‘upstream’ protein kinases in the MyD88 signalling network, and nor did it prevent the autophosphorylation of IRAK4 induced by LPS in RAW macrophages (Figure 3A) or IL-1 in IL-1R cells (Figure 3B). The suppression of K63-pUb chains and/or linear-pUb chains presumably explains how BAY 11-7082 prevents the activation of the IKK subfamily of protein kinases by LPS and IL-1. Biochem J. 2013 May 1; 451(Pt 3): 427–437. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3685219/
In vivo activity: It is hypothesized that short-term in vivo topical application of NF-κB inhibitor BAY 11-7082 can prevent acidic bile-induced early preneoplastic molecular events, suggesting its potential role in disease prevention. Murine hypoharyngeal (HM) (C57Bl/6j wild-type) were topically exposed to a mixture of bile acids at pH 3.0 with and without BAY 11-7082 3 times/day for 7 days. Immunofluorescence, Western blotting, immunohistochemistry, quantitative polymerase chain reaction, and polymerase chain reaction microarrays were used to identify NF-κB activation and its associated oncogenic mRNA and miRNA phenotypes, in murine hypopharyngeal cells in vitro and in murine HM in vivo. Short-term exposure of HM to acidic bile is a potent stimulus accelerating the expression of NF-κB signaling (70 out of 84 genes) and oncogenic molecules. Topical application of BAY 11-7082 sufficiently blocks the effect of acidic bile. BAY 11-7082 eliminates NF-κB activation in regenerating basal cells of acidic bile-treated HM and prevents overexpression of molecules central to head and neck cancer, including bcl-2, STAT3, EGFR, TNF-α, and WNT5A. NF-κB inhibitor reverses the upregulated "oncomirs" miR-155 and miR-192 and the downregulated "tumor suppressors" miR-451a and miR-375 phenotypes in HM affected by acidic bile. There is novel evidence that acidic bile-induced NF-κB-related oncogenic mRNA and miRNA phenotypes are generated after short-term 7-day mucosal exposure and that topical mucosal application of BAY 11-7082 can prevent the acidic bile-induced molecular alterations associated with unregulated cell growth and proliferation of hypopharyngeal cells. Neoplasia. 2018 Apr;20(4):374-386. https://pubmed.ncbi.nlm.nih.gov/29529473/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 55.0 267.00

Preparing Stock Solutions

The following data is based on the product molecular weight 207.25 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
Formulation protocol: 1. Strickson S, Campbell DG, Emmerich CH, Knebel A, Plater L, Ritorto MS, Shpiro N, Cohen P. The anti-inflammatory drug BAY 11-7082 suppresses the MyD88-dependent signalling network by targeting the ubiquitin system. Biochem J. 2013 May 1;451(3):427-37. doi: 10.1042/BJ20121651. PMID: 23441730; PMCID: PMC3685219. 2. Wang Y, Zhang XL, Sun CM. BAY-11-7082 induces apoptosis of multiple myeloma U266 cells through inhibiting NF-κB pathway. Eur Rev Med Pharmacol Sci. 2018 May;22(9):2564-2571. doi: 10.26355/eurrev_201805_14949. PMID: 29771406. 3.Sasaki CT, Doukas SG, Vageli DP. In Vivo Short-Term Topical Application of BAY 11-7082 Prevents the Acidic Bile-Induced mRNA and miRNA Oncogenic Phenotypes in Exposed Murine Hypopharyngeal Mucosa. Neoplasia. 2018 Apr;20(4):374-386. doi: 10.1016/j.neo.2018.02.001. Epub 2018 Mar 9. PMID: 29529473; PMCID: PMC5909679. 4. Vageli DP, Kasle D, Doukas SG, Doukas PG, Sasaki CT. The temporal effects of topical NF-κB inhibition, in the in vivo prevention of bile-related oncogenic mRNA and miRNA phenotypes in murine hypopharyngeal mucosa: a preclinical model. Oncotarget. 2020 Sep 1;11(35):3303-3314. doi: 10.18632/oncotarget.27706. PMID: 32934775; PMCID: PMC7476734.
In vitro protocol: 1. Strickson S, Campbell DG, Emmerich CH, Knebel A, Plater L, Ritorto MS, Shpiro N, Cohen P. The anti-inflammatory drug BAY 11-7082 suppresses the MyD88-dependent signalling network by targeting the ubiquitin system. Biochem J. 2013 May 1;451(3):427-37. doi: 10.1042/BJ20121651. PMID: 23441730; PMCID: PMC3685219. 2. Wang Y, Zhang XL, Sun CM. BAY-11-7082 induces apoptosis of multiple myeloma U266 cells through inhibiting NF-κB pathway. Eur Rev Med Pharmacol Sci. 2018 May;22(9):2564-2571. doi: 10.26355/eurrev_201805_14949. PMID: 29771406.
In vivo protocol: 1. Sasaki CT, Doukas SG, Vageli DP. In Vivo Short-Term Topical Application of BAY 11-7082 Prevents the Acidic Bile-Induced mRNA and miRNA Oncogenic Phenotypes in Exposed Murine Hypopharyngeal Mucosa. Neoplasia. 2018 Apr;20(4):374-386. doi: 10.1016/j.neo.2018.02.001. Epub 2018 Mar 9. PMID: 29529473; PMCID: PMC5909679. 2. Vageli DP, Kasle D, Doukas SG, Doukas PG, Sasaki CT. The temporal effects of topical NF-κB inhibition, in the in vivo prevention of bile-related oncogenic mRNA and miRNA phenotypes in murine hypopharyngeal mucosa: a preclinical model. Oncotarget. 2020 Sep 1;11(35):3303-3314. doi: 10.18632/oncotarget.27706. PMID: 32934775; PMCID: PMC7476734.

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Kolati SR, Kasala ER, Bodduluru LN, Mahareddy JR, Uppulapu SK, Gogoi R, Barua CC, Lahkar M. BAY 11-7082 ameliorates diabetic nephropathy by attenuating hyperglycemia-mediated oxidative stress and renal inflammation via NF-κB pathway. Environ Toxicol Pharmacol. 2015 Mar;39(2):690-9. doi: 10.1016/j.etap.2015.01.019. Epub 2015 Feb 7. PubMed PMID: 25704036.

2: Chen L, Ruan Y, Wang X, Min L, Shen Z, Sun Y, Qin X. BAY 11-7082, a nuclear factor-κB inhibitor, induces apoptosis and S phase arrest in gastric cancer cells. J Gastroenterol. 2014 May;49(5):864-74. doi: 10.1007/s00535-013-0848-4. Epub 2013 Jul 12. PubMed PMID: 23846545.

3: Krishnan N, Bencze G, Cohen P, Tonks NK. The anti-inflammatory compound BAY-11-7082 is a potent inhibitor of protein tyrosine phosphatases. FEBS J. 2013 Jun;280(12):2830-41. doi: 10.1111/febs.12283. Epub 2013 May 9. PubMed PMID: 23578302; PubMed Central PMCID: PMC3712534.

4: Rauert-Wunderlich H, Siegmund D, Maier E, Giner T, Bargou RC, Wajant H, Stühmer T. The IKK inhibitor Bay 11-7082 induces cell death independent from inhibition of activation of NFκB transcription factors. PLoS One. 2013;8(3):e59292. doi: 10.1371/journal.pone.0059292. Epub 2013 Mar 20. PubMed PMID: 23527154; PubMed Central PMCID: PMC3603909.

5: Strickson S, Campbell DG, Emmerich CH, Knebel A, Plater L, Ritorto MS, Shpiro N, Cohen P. The anti-inflammatory drug BAY 11-7082 suppresses the MyD88-dependent signalling network by targeting the ubiquitin system. Biochem J. 2013 May 1;451(3):427-37. doi: 10.1042/BJ20121651. PubMed PMID: 23441730; PubMed Central PMCID: PMC3685219.

6: Lee J, Rhee MH, Kim E, Cho JY. BAY 11-7082 is a broad-spectrum inhibitor with anti-inflammatory activity against multiple targets. Mediators Inflamm. 2012;2012:416036. doi: 10.1155/2012/416036. Epub 2012 Jun 15. PubMed PMID: 22745523; PubMed Central PMCID: PMC3382285.

7: Catalán U, Fernández-Castillejo S, Pons L, Heras M, Aragonés G, Anglès N, Morelló JR, Solà R. Alpha-tocopherol and BAY 11-7082 reduce vascular cell adhesion molecule in human aortic endothelial cells. J Vasc Res. 2012;49(4):319-28. doi: 10.1159/000337466. Epub 2012 May 9. PubMed PMID: 22572606.

8: Kumar A, Negi G, Sharma SS. Suppression of NF-κB and NF-κB regulated oxidative stress and neuroinflammation by BAY 11-7082 (IκB phosphorylation inhibitor) in experimental diabetic neuropathy. Biochimie. 2012 May;94(5):1158-65. doi: 10.1016/j.biochi.2012.01.023. Epub 2012 Feb 7. PubMed PMID: 22342224.

9: Ghashghaeinia M, Toulany M, Saki M, Bobbala D, Fehrenbacher B, Rupec R, Rodemann HP, Ghoreschi K, Röcken M, Schaller M, Lang F, Wieder T. The NFĸB pathway inhibitors Bay 11-7082 and parthenolide induce programmed cell death in anucleated Erythrocytes. Cell Physiol Biochem. 2011;27(1):45-54. doi: 10.1159/000325204. Epub 2011 Feb 11. PubMed PMID: 21325821.

10: Gruchlik A, Chodurek E, Zajdel A, Wilczok A, Weglarz L, Dzierzewicz Z. Influence of troglitazone, sodium butyrate, 5-aminosalicylic acid and BAY 11-7082 on the chemokine ENA-78/CXCL5 secretion in the intestinal subepithelial myofibroblasts. Acta Pol Pharm. 2010 Nov-Dec;67(6):690-5. PubMed PMID: 21229889.

11: Kim YS, Kim JS, Kwon JS, Jeong MH, Cho JG, Park JC, Kang JC, Ahn Y. BAY 11-7082, a nuclear factor-κB inhibitor, reduces inflammation and apoptosis in a rat cardiac ischemia-reperfusion injury model. Int Heart J. 2010;51(5):348-53. PubMed PMID: 20966608.

12: Miyamoto R, Ito T, Nomura S, Amakawa R, Amuro H, Katashiba Y, Ogata M, Murakami N, Shimamoto K, Yamazaki C, Hoshino K, Kaisho T, Fukuhara S. Inhibitor of IkappaB kinase activity, BAY 11-7082, interferes with interferon regulatory factor 7 nuclear translocation and type I interferon production by plasmacytoid dendritic cells. Arthritis Res Ther. 2010;12(3):R87. doi: 10.1186/ar3014. Epub 2010 May 14. PubMed PMID: 20470398; PubMed Central PMCID: PMC2911871.

13: Juliana C, Fernandes-Alnemri T, Wu J, Datta P, Solorzano L, Yu JW, Meng R, Quong AA, Latz E, Scott CP, Alnemri ES. Anti-inflammatory compounds parthenolide and Bay 11-7082 are direct inhibitors of the inflammasome. J Biol Chem. 2010 Mar 26;285(13):9792-802. doi: 10.1074/jbc.M109.082305. Epub 2010 Jan 21. PubMed PMID: 20093358; PubMed Central PMCID: PMC2843228.

14: Meng X, Martinez MA, Raymond-Stintz MA, Winter SS, Wilson BS. IKK inhibitor bay 11-7082 induces necroptotic cell death in precursor-B acute lymphoblastic leukaemic blasts. Br J Haematol. 2010 Feb;148(3):487-90. doi: 10.1111/j.1365-2141.2009.07988.x. Epub 2009 Dec 1. PubMed PMID: 19958360.

15: Lee HS, Kim SD, Lee WM, Endale M, Kamruzzaman SM, Oh WJ, Cho JY, Kim SK, Cho HJ, Park HJ, Rhee MH. A noble function of BAY 11-7082: Inhibition of platelet aggregation mediated by an elevated cAMP-induced VASP, and decreased ERK2/JNK1 phosphorylations. Eur J Pharmacol. 2010 Feb 10;627(1-3):85-91. doi: 10.1016/j.ejphar.2009.11.005. Epub 2009 Nov 10. PubMed PMID: 19913011.

16: White DE, Burchill SA. BAY 11-7082 induces cell death through NF-kappaB-independent mechanisms in the Ewing's sarcoma family of tumours. Cancer Lett. 2008 Sep 18;268(2):212-24. doi: 10.1016/j.canlet.2008.03.045. Epub 2008 May 8. PubMed PMID: 18471963.

17: Wang L, Liu LB, Li L, Zou P. [Enhancement of Fas-mediated apoptosis in leukemic cell line HL-60 by Bay 11 - 7082]. Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2007 Oct;15(5):941-5. Chinese. PubMed PMID: 17956666.

18: Hewavitharana AK, Hyde C, Thomas R, Shaw PN. Shortcomings of protein removal prior to high performance liquid chromatographic analysis-A case study using method development for BAY 11-7082. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Apr 13;834(1-2):93-7. Epub 2006 Mar 10. PubMed PMID: 16530027.

19: Hansson A, Marín YE, Suh J, Rabson AB, Chen S, Huberman E, Chang RL, Conney AH, Zheng X. Enhancement of TPA-induced growth inhibition and apoptosis in myeloid leukemia cells by BAY 11-7082, an NF-kappaB inhibitor. Int J Oncol. 2005 Oct;27(4):941-8. PubMed PMID: 16142309.

20: García MG, Alaniz L, Lopes EC, Blanco G, Hajos SE, Alvarez E. Inhibition of NF-kappaB activity by BAY 11-7082 increases apoptosis in multidrug resistant leukemic T-cell lines. Leuk Res. 2005 Dec;29(12):1425-34. Epub 2005 Jun 27. PubMed PMID: 15982733.