19542-67-7

19542-67-7 structure

Name: BAY 11-7082
Chemical Name: (E)-3-tosylacrylonitrile
CAS Number: 19542-67-7
Molecular Formula: C₁₀H₉NO₂S
Molecular Weight: 207.249
Catalog: Biochemical Inhibitor Nuclear transcription factor (NF-κB) IκB/IKK inhibitor
Create Date: 2018-07-31 13:09:37
Modify Date: 2024-01-02 18:47:28
BAY 11-7082 is a NF-κB inhibitor which decreases NF-κB by inhibiting TNF-α-induced phosphorylation of IκB-α. BAY 11-7082 inhibits ubiquitin-specific protease USP7 and USP21 with IC50s of 0.19 μM and 0.96 μM, respectively.

Name	(E)-3-tosylacrylonitrile
Synonyms	3-(p-Tolylsulfonyl)acrylonitrile 3-(p-Toluenesulfonyl)acrylonitrile (E)-3-Tosylacrylonitrile (2E)-3-[(4-Methylphenyl)sulfonyl]acrylonitrile (E)-3-(4-Methylphenylsulfonyl)-2-propenenitrile (E)-3-(4-methylphenyl)sulfonylprop-2-enenitrile 3-((4-Methylphenyl)sulfonyl)-2-propenenitrile BAY-11-7082 2-Propenenitrile, 3-((4-methylphenyl)sulfonyl)- BAY 11-7082 (2E)-3-[(4-methylphenyl)sulfonyl]prop-2-enenitrile 2-Propenenitrile, 3-[(4-methylphenyl)sulfonyl]-, (2E)- (E)-3-(p-Toluenesulfonyl)acrylonitrile BAY11-7082

Description	BAY 11-7082 is a NF-κB inhibitor which decreases NF-κB by inhibiting TNF-α-induced phosphorylation of IκB-α. BAY 11-7082 inhibits ubiquitin-specific protease USP7 and USP21 with IC50s of 0.19 μM and 0.96 μM, respectively.
Related Catalog	Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Cell Cycle/DNA Damage >> Deubiquitinase Signaling Pathways >> NF-κB >> NF-κB Research Areas >> Inflammation/Immunology
Target	NF-κB USP7:0.19 μM (IC50) USP21:0.96 μM (IC50) Autophagy
In Vitro	Bay 11-7082, an inhibitor of NF-κB, induces apoptosis of HTLV-I-infected T-cell lines but only negligible apoptosis of HTLV-I-negative T cells. Bay 11-7082 rapidly and efficiently reduces the DNA binding of NF-κB in HTLV-I-infected T-cell lines and down-regulated the expression of the antiapoptotic gene, Bcl-xL, regulated by NF-κB. Bay 11-7082 selectively inhibits Tax-induced NF-κB activity in a human T-cell line[1]. BAY 11-7082 inhibits NFκB signalling and is recently shown to inhibit the majority of E2 and E3 ligases tested by reacting covalently with the catalytic cysteine residues. Moreover, BAY 11-7082 also inhibits several tyrosine phosphatases by reacting with catalytic Cys residue of these enzymes. NSC 697923 is originally shown to inhibit the E2 ligase Ubc13-Uev1A[2]. BAY 11-7082 inhibits the phosphorylation of IκBα and activation of NF-κB, induces the death of HBL-1 cells. BAY 11-7082 completely suppresses the LPS-stimulated and IL-1-stimulated phosphorylation of the activation loop of IKKβ[3]. BAY 11-7082 acts by inhibiting TNF-α-induced phosphorylation of IκB-α, resulting in decreased NF-κB and decreases expression of adhesion molecules[4].
Kinase Assay	UBE1 (0.17 μM) in 22.5 μL of 20 mM Hepes, pH 7.5, containing 10 μM ubiquitin is incubated for 45 min at 21°C with 1 μL of DMSO or 1 μL of BAY 11-7082 in DMSO. A 2.5 μL solution of 10 mM magnesium acetate and 0.2 mM ATP is added, incubated for 10 min at 30°C, and the reactions are terminated by the addition of 2.5 μL of 10% (w/v) SDS and heating for 6 min at 75°C. The samples are subjected to SDS/PAGE in the absence of any thiol. The gels are stained for 1 h with Coomassie Instant Blue and destained by washing with water. The loading of ubiquitin to E2 conjugating enzymes is carried out in an identical manner, except that UBE1 (0.17 μM) is mixed with Ubc13 (2.4 μM) or UbcH7 (2.9 μM) prior to incubation with BAY 11-7082[3].
Cell Assay	The effect of Bay 11-7082 on cell growth is assayed by the WST-1 method. 2×104 (cell lines) or 2×105 (PBMCs) cells are incubated in a 96-well microculture plate under the above conditions in the absence or presence of various concentrations of Bay 11-7082 (1, 2, 3, 4, and 5 μM). After 48 hours of culture, 10 μL WST-1 solution is added and the cells are further incubated for another 2 hours. The number of surviving cells is measured with a microplate reader at a reference wavelength of 655 nm and test wavelength of 450 nm. Cell viability is determined as percentage of the control (ie, absence of Bay 11-7082)[1].
References	[1]. Mori N, et al. Bay 11-7082 inhibits transcription factor NF-kappaB and induces apoptosis of HTLV-I-infected T-cell lines andprimary adult T-cell leukemia cells. Blood. 2002 Sep 1;100(5):1828-1834. [2]. Ritorto MS, et al. Screening of DUB activity and specificity by MALDI-TOF mass spectrometry. Nat Commun. 2014 Aug 27;5:4763. [3]. Strickson S, et al. The anti-inflammatory drug BAY 11-7082 suppresses the MyD88-dependent signalling network by targeting the ubiquitin system. Biochem J. 2013 May 1;451(3):427-437. [4]. Pierce JW, et al. Novel inhibitors of cytokine-induced IkappaBalpha phosphorylation and endothelial cell adhesion molecule expression show anti-inflammatory effects in vivo. J Biol Chem. 1997 Aug 22;272(34):21096-103.

Density	1.2±0.1 g/cm3
Boiling Point	397.6±42.0 °C at 760 mmHg
Melting Point	133-135℃
Molecular Formula	C₁₀H₉NO₂S
Molecular Weight	207.249
Flash Point	194.3±27.9 °C
Exact Mass	207.035400
PSA	66.31000
LogP	1.28
Appearance	solid \| white
Vapour Pressure	0.0±0.9 mmHg at 25°C
Index of Refraction	1.557
Storage condition	Store at +4°C
Water Solubility	DMSO: 25 mg/mL, soluble

Personal Protective Equipment	Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
RIDADR	NONH for all modes of transport
WGK Germany	3
RTECS	UD1430000

Precursor 9
824-79-3 107-13-1 77825-72-0 151-50-8
86409-95-2 86409-89-4 68819-94-3 1950-78-3
4554-16-9
DownStream 2
1950-69-2 715-12-8

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