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Merck
CN

5.30536

EGFR Activator, NSC 228155

Synonym(s):

EGFR Activator, NSC 228155, 4-Nitro-7-((1-oxidopyridin-2-yl)sulfanyl)-2,1,3-benzoxadiazole, 4-Nitro-7-(1-oxy-pyridin-2-ylsulfanyl)-benzo[1,2,5]oxadiazole, 2-(7-Nitrobenzo[c][1,2,5]oxadiazol-4-ylthio)pyridine-1-oxide, NSC-228155

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About This Item

Empirical Formula (Hill Notation):
C11H6N4O4S
CAS Number:
113104-25-9
Molecular Weight:
290.25
MDL number:
MFCD30742994
UNSPSC Code:
41121801
NACRES:
NA.77
Assay:
≥97% (HPLC)
Form:
powder
Quality level:
100
Storage condition:
OK to freeze
desiccated (hygroscopic)
protect from light

Key Documents

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InChI key

ICCFXXDUYSPKOL-UHFFFAOYSA-N

SMILES string

S(c3[n+](cccc3)[O-])c1c2n[o]nc2c(cc1)[N+](=O)[O-]

assay

≥97% (HPLC)

form

powder

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
desiccated (hygroscopic)
protect from light

color

burnt orange

solubility

DMSO: 5 mg/mL

storage temp.

2-8°C

Quality Level

100

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Biochem/physiol Actions

Cell permeable: yes
Primary Target
EGF receptor

Disclaimer

Toxicity: Standard Handling (A)

General description

A nitro-benzoxadiazole (NBD) compound that directly binds to the dimerization domain of sEGF receptor to generate stable dimers and allosterically activates the receptor. Exhibits similar phosphorylation profile as the cognate EGF-ligand. Enhances the phosphorylation of Tyr1068 and Tyr1173 in MDA-MB-468 cells in a time- and dose-dependent manner (EC50 = 52 µM with respect to Tyr1068). These phosphorylation events can be blocked by pre-incubating cells with AG1478 (>Cat. No. 658852; 10 µM) or PD153035 (https://www.emdmillipore.com/US/en/product/Complement-C9-Depleted-Serum-Human,EMD_BIO-234409">>Cat. No. 234490; 2 µM) that selectively block the ATP-binding pocket of EGFR. Tyr1068 phosphorylation of the receptor can also be completely blocked in EGF treated MDA-MB-468 cells exposed to anti-EGFR neutralizing antibody.

Other Notes

Sakanyan, V., et al. 2014. Sci. Rep.4, 3977.

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
Use only fresh DMSO for reconstitution.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Vehary Sakanyan et al.
Scientific reports, 4, 3977-3977 (2014-02-06)
Peptide ligand-induced dimerization of the extracellular region of the epidermal growth factor receptor (sEGFR) is central to the signal transduction of many cellular processes. A small molecule microarray screen has been developed to search for non-peptide compounds able to bind

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