BAY 11-7085
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MedKoo CAT#: 522393

CAS#: 196309-76-9

Description: BAY 11-7085, a soluble inhibitor of NK-kappaB activation, has been shown to inhibit cell proliferation and induce apoptosis of a variety of cells. BAY 11-7085 induces apoptosis of ECSCs by suppressing antiapoptotic proteins, and that caspase-3-, -8-, and -9-mediated cascades are involved in this mechanism. BAY 11-7085 could be used as a therapeutic agent for the treatment of endometriosis. BAY 11-7085 protects against gut ischemia-reperfusion injury.


Chemical Structure

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BAY 11-7085
CAS# 196309-76-9

Theoretical Analysis

MedKoo Cat#: 522393
Name: BAY 11-7085
CAS#: 196309-76-9
Chemical Formula: C13H15NO2S
Exact Mass: 249.08
Molecular Weight: 249.330
Elemental Analysis: C, 62.63; H, 6.06; N, 5.62; O, 12.83; S, 12.86

Price and Availability

Size Price Availability Quantity
25mg USD 110 Ready to ship
50mg USD 180 Ready to ship
100mg USD 300 Ready to ship
200mg USD 500 Ready to ship
500mg USD 1050 Ready to ship
1g USD 1850 2 weeks
2g USD 2950 2 weeks
5g USD 4650 2 weeks
Bulk inquiry

Synonym: Bay 11-7085; Bay-11-7085; Bay11-7085; Bay 117085; Bay-117085; Bay117085.

IUPAC/Chemical Name: (2E)-3-[[4-(1,1-Dimethylethyl)phenyl]sulfonyl]-2-propenenitrile

InChi Key: VHKZGNPOHPFPER-ONNFQVAWSA-N

InChi Code: InChI=1S/C13H15NO2S/c1-13(2,3)11-5-7-12(8-6-11)17(15,16)10-4-9-14/h4-8,10H,1-3H3/b10-4+

SMILES Code: N#C/C=C/S(=O)(C1=CC=C(C(C)(C)C)C=C1)=O

Appearance: White to off white 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 11-7085 (Bay 11-7083) is an inhibitor of TNFα-induced IκBα phosphorylation with an IC50 of 10 μM.
In vitro activity: BAY 11-7085 induced an increase of autophagosomal marker LC3B-II, a lipidated form of LC3B, from 10-60 minutes, that ceased and that was down regulated from 90-120 min of cell treatment (Figure 1). BAY 11-7085 also induced GR (glucocorticoid receptor) phosphorylation of Serine 211 (Figure 1). Furthermore, BAY 11-7085 markedly down regulated GR expression (Figure 1). These results suggested that BAY 11-7085-induced autophagy and GR activation might be interconnected. Reference: Oncotarget. 2016 Apr 26;7(17):23370-82. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5029633/
In vivo activity: The involvement of NF-kappaB and the processes regulated by NF-kappaB in the initial development of endometriotic lesions was investigated in a mouse model of endometriosis. BAY 11-7085 induced a significant reduction in lesion development compared to control mice. NF-kappaB activation and ICAM-1 expression of endometriotic lesions were significantly reduced in treated mice, and cell proliferation was significantly reduced in BAY 11-7085-treated mice. BAY 11-7085 produced a significant increase in apoptosis of endometriotic lesions, as assessed by active caspase-3 immunostaining and the TUNEL method. Reference: Gynecol Obstet Invest. 2008;65(3):174-86. https://www.karger.com/Article/Abstract/111148

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 30.2 121.24
Ethanol 31.6 126.90

Preparing Stock Solutions

The following data is based on the product molecular weight 249.33 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. Relic B, Charlier E, Deroyer C, Malaise O, Neuville S, Desoroux A, Gillet P, de Seny D, Malaise MG. BAY 11-7085 induces glucocorticoid receptor activation and autophagy that collaborate with apoptosis to induce human synovial fibroblast cell death. Oncotarget. 2016 Apr 26;7(17):23370-82. doi: 10.18632/oncotarget.8042. PMID: 26993765; PMCID: PMC5029633. 2. Nasu K, Nishida M, Ueda T, Yuge A, Takai N, Narahara H. Application of the nuclear factor-kappaB inhibitor BAY 11-7085 for the treatment of endometriosis: an in vitro study. Am J Physiol Endocrinol Metab. 2007 Jul;293(1):E16-23. doi: 10.1152/ajpendo.00135.2006. Epub 2006 Aug 8. PMID: 16896168. 3. González-Ramos R, Van Langendonckt A, Defrère S, Lousse JC, Mettlen M, Guillet A, Donnez J. Agents blocking the nuclear factor-kappaB pathway are effective inhibitors of endometriosis in an in vivo experimental model. Gynecol Obstet Invest. 2008;65(3):174-86. doi: 10.1159/000111148. Epub 2007 Nov 20. PMID: 18025832. 4. Politz O, Siegel F, Bärfacker L, Bömer U, Hägebarth A, Scott WJ, Michels M, Ince S, Neuhaus R, Meyer K, Fernández-Montalván AE, Liu N, von Nussbaum F, Mumberg D, Ziegelbauer K. BAY 1125976, a selective allosteric AKT1/2 inhibitor, exhibits high efficacy on AKT signaling-dependent tumor growth in mouse models. Int J Cancer. 2017 Jan 15;140(2):449-459. doi: 10.1002/ijc.30457. Epub 2016 Oct 20. PMID: 27699769.
In vitro protocol: 1. Relic B, Charlier E, Deroyer C, Malaise O, Neuville S, Desoroux A, Gillet P, de Seny D, Malaise MG. BAY 11-7085 induces glucocorticoid receptor activation and autophagy that collaborate with apoptosis to induce human synovial fibroblast cell death. Oncotarget. 2016 Apr 26;7(17):23370-82. doi: 10.18632/oncotarget.8042. PMID: 26993765; PMCID: PMC5029633. 2. Nasu K, Nishida M, Ueda T, Yuge A, Takai N, Narahara H. Application of the nuclear factor-kappaB inhibitor BAY 11-7085 for the treatment of endometriosis: an in vitro study. Am J Physiol Endocrinol Metab. 2007 Jul;293(1):E16-23. doi: 10.1152/ajpendo.00135.2006. Epub 2006 Aug 8. PMID: 16896168.
In vivo protocol: 1. González-Ramos R, Van Langendonckt A, Defrère S, Lousse JC, Mettlen M, Guillet A, Donnez J. Agents blocking the nuclear factor-kappaB pathway are effective inhibitors of endometriosis in an in vivo experimental model. Gynecol Obstet Invest. 2008;65(3):174-86. doi: 10.1159/000111148. Epub 2007 Nov 20. PMID: 18025832. 2. Politz O, Siegel F, Bärfacker L, Bömer U, Hägebarth A, Scott WJ, Michels M, Ince S, Neuhaus R, Meyer K, Fernández-Montalván AE, Liu N, von Nussbaum F, Mumberg D, Ziegelbauer K. BAY 1125976, a selective allosteric AKT1/2 inhibitor, exhibits high efficacy on AKT signaling-dependent tumor growth in mouse models. Int J Cancer. 2017 Jan 15;140(2):449-459. doi: 10.1002/ijc.30457. Epub 2016 Oct 20. PMID: 27699769.

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1: Relic B, Charlier E, Deroyer C, Malaise O, Neuville S, Desoroux A, Gillet P, de Seny D, Malaise MG. BAY 11-7085 induces glucocorticoid receptor activation and autophagy that collaborate with apoptosis to induce human synovial fibroblast cell death. Oncotarget. 2016 Apr 26;7(17):23370-82. doi: 10.18632/oncotarget.8042. PubMed PMID: 26993765; PubMed Central PMCID: PMC5029633.

2: Berger N, Ben Bassat H, Klein BY, Laskov R. Cytotoxicity of NF-kappaB inhibitors Bay 11-7085 and caffeic acid phenethyl ester to Ramos and other human B-lymphoma cell lines. Exp Hematol. 2007 Oct;35(10):1495-509. PubMed PMID: 17889719.

3: Nasu K, Nishida M, Ueda T, Yuge A, Takai N, Narahara H. Application of the nuclear factor-kappaB inhibitor BAY 11-7085 for the treatment of endometriosis: an in vitro study. Am J Physiol Endocrinol Metab. 2007 Jul;293(1):E16-23. PubMed PMID: 16896168.

4: Relic B, Benoit V, Franchimont N, Kaiser MJ, Hauzeur JP, Gillet P, Merville MP, Bours V, Malaise MG. Peroxisome proliferator-activated receptor-gamma1 is dephosphorylated and degraded during BAY 11-7085-induced synovial fibroblast apoptosis. J Biol Chem. 2006 Aug 11;281(32):22597-604. PubMed PMID: 16766531.

5: Hernández-Gutierrez S, García-Peláez I, Zentella-Dehesa A, Ramos-Kuri M, Hernández-Franco P, Hernández-Sánchez F, Rojas E. NF-kappaB signaling blockade by Bay 11-7085 during early cardiac morphogenesis induces alterations of the outflow tract in chicken heart. Apoptosis. 2006 Jul;11(7):1101-9. PubMed PMID: 16699956.

6: Cory AH, Cory JG. Induction of apoptosis in p53-deficient L1210 cells by an I-kappa-B-alpha-inhibitor (Bay 11-7085) via a NF-kappa-B-independent mechanism. Adv Enzyme Regul. 2005;45:85-93. PubMed PMID: 16129475.

7: Relic B, Benoit V, Franchimont N, Ribbens C, Kaiser MJ, Gillet P, Merville MP, Bours V, Malaise MG. 15-deoxy-delta12,14-prostaglandin J2 inhibits Bay 11-7085-induced sustained extracellular signal-regulated kinase phosphorylation and apoptosis in human articular chondrocytes and synovial fibroblasts. J Biol Chem. 2004 May 21;279(21):22399-403. PubMed PMID: 15004016.

8: Zou L, Sato N, Attuwaybi BO, Kone BC. Delayed administration of alpha-melanocyte-stimulating hormone or combined therapy with BAY 11-7085 protects against gut ischemia-reperfusion injury. Shock. 2003 Nov;20(5):469-75. PubMed PMID: 14560113.