BAY 11-7082
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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.


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100mg
USD 150
1g
USD 650
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200mg
USD 250
2g
USD 1050
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500mg
USD 450
5g
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BAY 11-7082, purity > 98%, is in stock. The same day shipping out after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 522392
Name: BAY 11-7082
CAS#: 19542-67-7
Chemical Formula: C10H9NO2S
Exact Mass: 207.0354
Molecular Weight: 207.25
Elemental Analysis: C, 57.96; H, 4.38; N, 6.76; O, 15.44; S, 15.47


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


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Certificate of Analysis:

Safety Data Sheet (MSDS):

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).

Harmonized System Code:
293490


References

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.