196309-76-9

Basic information

• Product Name: BAY 11-7085
• Synonyms: BAY 117083 (2E)-3-[[4-(1,1-Dimethylethyl)phenyl]sulfonyl]-2-propenenitrile;(2E)-3-[[4-(1,1-DIMETHYLETHYL)PHENYL]SULFONYL]-2-PROPENENITRILE;(E)-3-(T-BUTYLPHENYLSULFONYL)-2-PROPENENITRILE;(E)3-[(4-T-BUTYLPHENYL)SULFONYL]-2-PROPENENITRILE;BAY 11-7085;(E)-3-(4-tert-butylphenylsulfonyl)acrylonitrile;BAY 117083;(2E)-3-[[4-(1,1-Dimethylethyl)phenyl]sulfonyl]-2-propenenitrile BAY 11-7085
• CAS NO: 196309-76-9
• Molecular Formula: C13H15NO2S
• Molecular Weight: 249.33
• Product Categories: Inhibitors;Cytokine signaling
• Mol File: 196309-76-9.mol
• Article Data: 0

Chemical Properties

• Melting Point: 80-82℃
• Boiling Point: 407.1 °C at 760 mmHg
• Flash Point: 200℃
• Appearance: white/solid
• Density: 1.144
• Vapor Pressure: 7.73E-07mmHg at 25°C
• Refractive Index: 1.534
• Storage Temp.: Store at +4°C
• Solubility: DMSO: >25 mg/mL, soluble
• Sensitive: Light Sensitive
• CAS DataBase Reference: BAY 11-7085(CAS DataBase Reference)
• NIST Chemistry Reference: BAY 11-7085(196309-76-9)
• EPA Substance Registry System: BAY 11-7085(196309-76-9)

Safety Data

• WGK Germany: 3
• RTECS: UD1312500
• Hazardous Substances Data: 196309-76-9(Hazardous Substances Data)

Usage

Description

BAY 11-7085 is a potent and irreversible inhibitor of IκBα phosphorylation, which plays a crucial role in the activation of the transcription factor nuclear factor-κB (NF-κB). By inhibiting IκBα phosphorylation, BAY 11-7085 prevents the activation of NF-κB, thereby blocking gene expression regulated through the classical pathway of NF-κB activation. This inhibition has significant implications for various cellular processes, including apoptosis, cell adhesion, and inflammation.

Uses

Used in Cellular and Molecular Research:
BAY 11-7085 is used as a nuclear factor-κB inhibitor for studying the role of NF-κB in various cellular processes and diseases. It is particularly useful in understanding the mechanisms underlying inflammation, apoptosis, and cell adhesion.
Used in Panc-1 Cells:
BAY 11-7085 is used as a nuclear factor-κB inhibitor in Panc-1 cells, a pancreatic cancer cell line, to investigate the role of NF-κB in cancer progression and to explore potential therapeutic strategies.
Used in Human Astrocytoma Cells (U87MGs):
BAY 11-7085 is used as a macrophages inhibitory κB kinase (IKK) inhibitor in human astrocytoma cells (U87MGs) to study the role of IKK in the regulation of NF-κB signaling and its implications in cancer development.
Used in Human Monocyte Cell Line (THP-1):
BAY 11-7085 is used as a phospho-p65 inhibitor in the human monocyte cell line THP-1 to investigate the role of NF-κB in immune cell activation and inflammation.

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. Anti-inflammatory in vivo .

Biochem/physiol Actions

Bay 11-7085 inactivates peroxisome proliferator-activated receptors γ (PPAR-γ) and increases the microtubule-associated proteins 1A/1B light chain 3B (LC3B), a marker of autophagy resulting in apoptosis in human synovial fibroblasts. It promotes apoptosis in pancreatic carcinoma and may serve as radiotherapy-sensitizing drug. BAY 11-7085 decreases B-cell lymphoma 2 (Bcl-2) by inhibiting pI-κBα (inhibitor of nuclear factor κ B kinase subunit α

references

[1]nasu k1, 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

InChI:InChI=1/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+