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B5681

Sigma-Aldrich

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:
196309-76-9
Molecular Weight:
249.33
MDL number:
MFCD01862602
UNSPSC Code:
12352200
PubChem Substance ID:
24278273
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

solid

color

white

solubility

DMSO: soluble >25 mg/mL
H2O: insoluble

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+

InChI key

VHKZGNPOHPFPER-ONNFQVAWSA-N

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
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)
Jun Yan et al.
Nature communications, 10(1), 448-448 (2019-01-27)
Few studies implicate immunoregulatory gene expression in tumor cells in arbitrating brain tumor progression. Here we show that fibrinogen-like protein 2 (FGL2) is highly expressed in glioma stem cells and primary glioblastoma (GBM) cells. FGL2 knockout in tumor cells did
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