NSC228155
- Product Name
- NSC228155
- CAS No.
- 113104-25-9
- Chemical Name
- NSC228155
- Synonyms
- NSC228155;NSC-228155;NSC 228155;NSC 228155, 10 mM in DMSO;EGFR Activator, NSC 228155;NSC228155;NSC-228155;NSC 228155;2,1,3-Benzoxadiazole, 4-nitro-7-[(1-oxido-2-pyridinyl)thio]-;2-[(7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)thio]pyridine 1-oxide;Epidermal growth factor receptor,Histone Acetyltransferase,EGFR,HER1,HATs,inhibit,Inhibitor,NSC-228155,HAT,Epigenetic Reader Domain,NSC 228155,ErbB-1
- CBNumber
- CB13159458
- Molecular Formula
- C11H6N4O4S
- Formula Weight
- 290.25
- MOL File
- 113104-25-9.mol
NSC228155 Property
- Boiling point:
- 627.3±65.0 °C(Predicted)
- Density
- 1.72±0.1 g/cm3(Predicted)
- storage temp.
- 2-8°C(protect from light)
- solubility
- ≥29 mg/mL in DMSO; insoluble in H2O; insoluble in EtOH
- form
- solid
- pka
- -1.48±0.10(Predicted)
- color
- Light yellow to orange
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 5.30536
- Product name
- EGFR Activator, NSC 228155
- Packaging
- 25 mg
- Price
- $231
- Updated
- 2025/07/31
- Product number
- 28856
- Product name
- NSC 228155
- Packaging
- 5mg
- Price
- $68
- Updated
- 2024/03/01
- Product number
- 28856
- Product name
- NSC 228155
- Packaging
- 10mg
- Price
- $121
- Updated
- 2024/03/01
- Product number
- 28856
- Product name
- NSC 228155
- Packaging
- 25mg
- Price
- $235
- Updated
- 2024/03/01
- Product number
- CS-0020796
- Product name
- NSC228155
- Purity
- >98.0%
- Packaging
- 5mg
- Price
- $50
- Updated
- 2021/12/16
NSC228155 Chemical Properties,Usage,Production
Uses
NSC 228155 is an activator of EGFR, binds to the extracellular region of EGFR and enhance tyrosine phosphorylation of EGFR[1]. NSC 228155 is also a potent inhibitor of KIX-KID interaction, inhibits kinase-inducible domain (KID) from CREB and KID-interacting domain (KIX) from CBP, with an IC50 of 0.36 μM[2].
Biological Activity
nsc228155 is a potent inhibitor of kix-kid interaction.cyclic-amp response-element binding protein (creb) is identified as a stimulus-activated transcription factor. its transcription activity needs its binding with creb-binding protein (cbp) after creb is phosphorylated at ser133. the domains involved for creb-cbp interaction are kinase-inducible domain (kid) from creb and kid-interacting domain (kix) from cbp.
Synthesis
10199-89-0
1121-31-9
113104-25-9
The reaction was carried out with 4-chloro-7-nitrobenzo[c][1,2,5]oxadiazole (NBD-Cl) and 2-mercapto-pyridine-N-oxide, mixed in a 1:1 molar ratio, and stirred at room temperature for 10 min. Formation of precipitate was observed during the reaction. Subsequently, acetone (10 mL/0.1 g raw material) was added to the reaction mixture and stirring was continued. Upon completion of the reaction, the precipitate was collected by filtration through a G3 glass filter. The precipitate was further purified by preparative thin layer chromatography (TLC) using silica gel GF254 as stationary phase and a mixture of dichloromethane and methanol (10:0.2 v/v) as mobile phase, which was repeated three times. The final product was obtained as an orange-colored solid in 46% yield with a melting point of 198-199°C (literature value 201-202°C). Analysis by electrospray ionization mass spectrometry (ESI-MS) yielded the molecular ion peak [M+H]+ m/z 291, which is consistent with the calculated value of the molecular formula C11H6N4SO4 (M=290). The results of elemental analysis were as follows: calculated values C 45.52%, H 2.08%, N 19.3%, S 11.05%; measured values C 45.45%, H 2.03%, N 19.26%, S 11.01%. NMR hydrogen spectrum (1H-NMR, DMSO-d6, δ ppm, J Hz): 8.70 (d, 1H, H-6, J=7.4), 8.44 (bd, 1H, H-13, J=6.5), 8.05 (d, 1H, H-5, J=7.4), 7.39 (td, 1H, H-12, J=6.5, 3.1), 7.27- 7.22 (m, 2H, H-10, H-11). NMR carbon spectrum (13C-NMR, DMSO-d6, δ ppm): 150.73 (C-7), 146.07 (C-9), 143.47 (C-4), 136.98 (C-3), 128.52 (C-8), 138.61 (C-13), 136.63 (C-5), 131.88 (C-6), and 125.98 (C-10 or C-11), 125.84 (C-10 or C-11), 124.32 (C-12). Fourier transform infrared spectra (FT-IR, ATR, solid, ν cm-1): 3101w, 3076m, 3039w, 1518vs, 1469m, 1422s, 1363m, 1330s, 1275m, 1250s, 1227m, 1140m, 1044w, 958w, 890m, 843w, 808w. 758m, 733w, 704w.
in vitro
previous study found that nsc228155 could dose-dependently inhibit kix–kid interaction as measured by the split rluc assay. in living hek 293t cells, nsc228155 could inhibit creb-mediated gene transcription with an ic50 of 2.09 μm. nsc228155 also inhibited vp16-creb-mediated gene transcription with an ic50 of 6.14 μm. though this was around 3-fold higher than the ic50 of creb-mediated gene transcription, such results indicated that nsc228155 was not particularly selective in inhibiting kix–kid interaction inside these living cells. therefore, although nsc228155 was a potent inhibitor of kix-kid interaction, it was not selective against creb-mediated gene transcription, and further sar studies identified a 4-aniline substituted analog displaying a higher selectivity index [1].
target
| EGFR
| KIX-KID 0.36 μM (IC 50 ) |
IC 50
0.36 μm for kix-kid interaction
References
[1] xie f, li bx, broussard c, xiao x. identification, synthesis and evaluation of substituted benzofurazans as inhibitors of creb-mediated gene transcription. bioorg med chem lett. 2013 oct 1;23(19):5371-5.
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