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Merck

B5681

Bay 11-7085

≥98% (HPLC), solid

Synonym(s):

(E)-3-(4-t-Butylphenylsulfonyl)-2-propenenitrile

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About This Item

Empirical Formula (Hill Notation):
C13H15NO2S
CAS Number:
Molecular Weight:
249.33
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:

Product Name

Bay 11-7085, ≥98% (HPLC), solid

InChI key

VHKZGNPOHPFPER-ONNFQVAWSA-N

SMILES string

CC(C)(C)c1ccc(cc1)S(=O)(=O)\C=C\C#N

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+

assay

≥98% (HPLC)

form

solid

color

white

solubility

DMSO: soluble >25 mg/mL
H2O: insoluble

Quality Level

Gene Information

human ... NFKB1(4790)

Application

Bay 11-7085 has been used as:
  • nuclear factor-κB inhibitor in Panc-1 cells, macrophages
  • inhibitory κB kinase IKK inhibitor in human astrocytoma cells U87MGs
  • phospho-p65 inhibitor human monocyte cell line THP-1

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
Inhibits NF-κB activated expression of ICAM-1, VCAM-1, E-selectin, IL-6 and IL-8.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Maturational differences in lung NF-kappaB activation and their role in tolerance to hyperoxia
Yang G, et al.
The Journal of Clinical Investigation, 114(5), 669-678 (2004)
Impact of Bay 11-7085 on radiosensitivity of pancreatic cancer cell line Sw1990
Shu C, et al.
International Journal of Clinical and Experimental Medicine, 9(6), 9322-9326 (2016)
Neat1 regulates oxidized low-density lipoprotein-induced inflammation and lipid uptake in macrophages via paraspeckle formation
Huang-Fu N, et al.
Molecular Medicine Reports, 17(2), 3092-3098 (2018)
BAY 11-7085 induces glucocorticoid receptor activation and autophagy that collaborate with apoptosis to induce human synovial fibroblast cell death
Relic B, et al.
Oncotarget, 7(17), 23370-23370 (2016)
Claudia Matteucci et al.
Cell death discovery, 6, 9-9 (2020-03-04)
Adult T cell leukemia/lymphoma (ATL) can be susceptible, at least transiently, to treatments with azidothymidine (AZT) plus IFNα and/or arsenic trioxide. However, the real role of AZT in this effect is still unclear. In fact, while reverse transcriptase (RT) inhibition

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