ChemicalBook > CAS DataBase List > BAY 11-7082

BAY 11-7082

Product Name
BAY 11-7082
CAS No.
19542-67-7
Chemical Name
BAY 11-7082
Synonyms
BAY E;100824;CS-608;BAY-11708;BAY 11-7821;BAY 11-7082;BAY 11-7082, >=98%;BAY11-7082/BAY117082;BAY11-7082,BAY 117821;BAY 11-7082 USP/EP/BP
CBNumber
CB9733804
Molecular Formula
C10H9NO2S
Formula Weight
207.25
MOL File
19542-67-7.mol
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BAY 11-7082 Property

Melting point:
133-135℃
Boiling point:
397.6±42.0 °C(Predicted)
Density 
1.237±0.06 g/cm3(Predicted)
storage temp. 
Keep in dark place,Inert atmosphere,2-8°C
solubility 
DMSO: 25 mg/mL, soluble
form 
solid
color 
white
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
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Safety

WGK Germany 
3
RTECS 
UD1430000
HS Code 
2926907090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
B5556
Product name
Bay 11-7082
Purity
≥98% (HPLC), powder
Packaging
10mg
Price
$127
Updated
2024/03/01
Sigma-Aldrich
Product number
196870
Product name
BAY 11-7082
Packaging
10mg
Price
$113
Updated
2024/03/01
TCI Chemical
Product number
T2846
Product name
BAY 11-7082
Purity
>98.0%(HPLC)(N)
Packaging
100mg
Price
$49
Updated
2024/03/01
TCI Chemical
Product number
T2846
Product name
BAY 11-7082
Purity
>98.0%(HPLC)(N)
Packaging
1g
Price
$294
Updated
2024/03/01
Cayman Chemical
Product number
10010266
Product name
BAY 11-7082
Purity
≥98%
Packaging
5mg
Price
$49
Updated
2024/03/01
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BAY 11-7082 Chemical Properties,Usage,Production

Description

BAY 11-7082 (19542-67-7)?inhibits cytokine-induced IκB-α phosphorylation via inhibition of IκB Kinase which results in inhibition of NFκB .1 Inhibits anchorage-independent growth of mammary epithelial cells induced with 4-hydroxyestradiol via inhibition of NFκB activation.2 Inhibits IFNα production and blocks nuclear translocation of IRF7 in plasmacytoid dendritic cells.3? Facilitates wound healing by inhibiting TNFα-induced MMP expression.4 A useful tool for probing the involvement of NFκB in physiological and pathophysiological processes.5? Cell permeable.

Uses

Bay 11-7082 has been used as:

  • a nuclear factor-kappa B (NF-kB) inhibitor to verify the action of the NF-kB signaling pathway in the production of interleukin (IL)-8
  • a nuclear factor-kappa B (NF-kB) inhibitor to study the role of NF-kB activation in Mycoplasma hyorhinis -induced epithelial-mesenchymal transition (EMT) and cell migration
  • a nod-like receptor family pyrin domain containing 3 (NLRP3) selective inhibitor to examine its effects on liver inflammation in mice after hematopoietic stem cell transplantation

Definition

ChEBI: A nitrile that is acrylonitrile in which the hydrogen located beta,trans to the cyano group is replaced by a tosyl group. It is an inhibitor of cytokine-induced IkappaB-alpha phosphorylation i cells.

General Description

Potential anti-inflammatory agent that selectively and irreversibly inhibits the TNF-α-inducible phosphorylation of IκBα (IC50 = 10 μM), resulting in a decreased expression of NF-κB and of adhesion molecules. Does not affect constitutive IκBα autophosphorylation. Inhibits TNF-α-induced surface expression of the endothelial-leukocyte cell adhesion molecules E-selectin, VCAM-1, and ICAM-1. A 100 mM (10 mg/483 μl) solution of BAY 11-7082 (Cat. No. 196871) in DMSO is also available is also available.

Biological Activity

Irreversible inhibitor of TNF- α -stimulated I κ B α phosphorylation (IC 50 ~ 10 μ M); leads to decreased NF- κ B and subsequent decreased expression of adhesion molecules. Also reversibly activates MAP kinases and stimulates apoptosis.

Biochem/physiol Actions

Bay 11-7082 acts as a selective inhibitor for nod-like receptor family pyrin domain containing 3 (NLRP3) inflammasome pathway. In addition, to the inhibition of nuclear factor-kappa B (NF-kB), Bay 11-7082 also triggers apoptosis in anucleated erythrocytes, human T-cell leukemia virus type I (HTLV-I)-infected T-cell lines and primary adult T-cell leukemia cells.

Enzyme inhibitor

This protein kinase inhibitor (FW = 207.31 g/mol; CAS 19542-67-7; lmax = 251 nm), also named 3-[(4-methylphenyl)sulfonyl]-(2E)-propenenitrile, targets NF-κB activation, selectively and irreversibly blocking TNF-α- induced phosphorylation of IκB-α without affecting phosphorylation of constitutive IκB-α. Mechanism of Inhibitory Action: NF-κB transcription factor regulates expression of inflammatory cytokines, various chemokines and immunoreceptors, as well as cell adhesion molecules. When stationed within the cytoplasm, NF-κB is kept inactive through its binding to the inhibitory factor IκB; however, certain stimuli result in IκB phosphorylation and ubiquitin-mediated degradation, freeing NF-κB for translocation to the nucleus. In endothelial cells, IκB-α phosphorylation and degradation occur within 15 min of TNFα treatment, allowing NF-κB to translocate to the nucleus to activate gene expression. Treatment of humnan vascular endothelial cells (HUVEC) with TNFα results in rapid loss of IκB-α from the cytoplasm. BAY11-7082 stabilizes IκB-α in a dose-dependent manner (IC50 ≈ 10 μM). There is a clear correlation between the concentration of drug that stabilizes IκB-α, the concentration that inhibits nuclear levels of NF-κB, and the concentration that inhibits adhesion molecule expression. More recent studies demonstrate that BAY 11- 7082 prevents ubiquitin conjugation to Ubc13 and UbcH7 by forming a covalent adduct with their cysteine residues via Michael addition at the C-3 atom of BAY 11-7082, followed by the release of 4-methylbenzenesulfinate. BAY 11-7082 stimulated Lys48-linked polyubiquitin chain formation in cells and protected Hypoxia-Inducible Factor-1α (HIF1α) from proteasomal degradation, suggesting it inhibits the proteasome. These results indicate that the anti-inflammatory effects of BAY 11-7082, its ability to induce B-cell lymphoma and leukemic T-cell death and to prevent the recruitment of proteins to sites of DNA damage are exerted via inhibition of components of the ubiquitin system– not by inhibiting NF-κB. BAY11-7082 also inhibits proliferation and promotes apoptosis in breast carcinoma MCF-7 cells by inhibiting phosphorylation of ATP citrate lyase.

storage

+4°C

References

1) Pierce et al. (1997) Novel inhibitor of cytokine-induced IkBα phosphorylation and endothelial cell adhesion molecule expression show anti-inflammatory effects in vivo; J. Biol. Chem., 272 21096 2) Park et al. (2009) 4-hydroxyestradiol induces anchorage-independent growth of human mammary epithelial cells via activation of IkappaB kinase: potential role of reactive oxygen species; Cancer Res., 69 2416 3) Miyamoto et al. (2010) 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., 12 R87 4) Xu et al. (2019) Bay 11-7082 facilitates wound healing by antagonizing mechanical injury – and TNF-α-induced expression of MMPs in posterior cruciate ligament; Connect. Tissue Res. 60 311 5) Kim et al. (2018) TNF-α induces human neural progenitor cell survival after oxygen-glucose deprivation by activating the NFκB pathway; Exp. Mol. Med., 50 14

BAY 11-7082 Preparation Products And Raw materials

Raw materials

Preparation Products

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BAY 11-7082 Suppliers

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View Lastest Price from BAY 11-7082 manufacturers

Career Henan Chemical Co
Product
BAY 11-7082 19542-67-7
Price
US $3.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
100KG
Release date
2020-01-30

19542-67-7, BAY 11-7082Related Search:


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  • Gene Regulation
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  • BioChemical
  • Cell Signaling and Neuroscience
  • Cell Biology
  • Cytokine signaling
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  • NF-kB