| Identification | Back Directory | [Name]
Stattic | [CAS]
19983-44-9 | [Synonyms]
Stattic
CS-1523
AKOS 1001
BUTTPARK 97\04-73
STAT3 Inhibitor V
Stattic USP/EP/BP
Stat3 inhibitor V, stattic
Stat three inhibitory compound
1,1-DIOXO-6-NITROBENZO(B)THIOPHENE
6-Nitrobenzo[b]thiophene1,1-dioxide
6-Nitro-benzo[b]thiophen-1,1-dioxid
6-Nitro-1-benzothiophene 1,1-dioxide
1,1-Dioxide-6-nitro-benzo[b]thiophene
Benzo[b]thiophene, 6-nitro-, 1,1-dioxide
6-NITRO-1H-1LAMBDA6-BENZO[B]THIOPHENE-1,1-DIONE
STAT3 Inhibitor V, Stattic - CAS 19983-44-9 - Calbiochem
6-Nitrobenzo[b]thiophene-1,1-dioxide, Stat three inhibitory compound | [Molecular Formula]
C8H5NO4S | [MDL Number]
MFCD00173799 | [MOL File]
19983-44-9.mol | [Molecular Weight]
211.19 |
| Chemical Properties | Back Directory | [Melting point ]
187-188 °C | [Boiling point ]
461.1±45.0 °C(Predicted) | [density ]
1.621±0.06 g/cm3(Predicted) | [storage temp. ]
Store at +4°C | [solubility ]
DMSO: >20mg/mL | [form ]
powder | [color ]
white to beige | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months. | [InChI]
InChI=1S/C8H5NO4S/c10-9(11)7-2-1-6-3-4-14(12,13)8(6)5-7/h1-5H | [InChIKey]
ZRRGOUHITGRLBA-UHFFFAOYSA-N | [SMILES]
C12=CC([N+]([O-])=O)=CC=C1C=CS2(=O)=O |
| Hazard Information | Back Directory | [Description]
Stattic (19983-44-9) is a STAT3 inhibitor that inhibits binding of tyrosine-phosphorylated peptides to STAT3 SH2 domain and inhibiting STAT3 activation, dimerization and nuclear translocation.1 Displays selectivity over STAT1, STAT5, c-Myc/Max, Jun/Jun and Lck. Induces apoptosis in STAT3-dependent cancer cell lines. Alkyates four cysteine residues on STAT3.2 Exhibits potent antitumor activity.3 Protects against angiotensin II-induced vascular dysfunction and hypertension.4?Stattic is an extremely useful tool to probe involvement of STAT3 in cellular signaling. | [Uses]
Stattic is a Stat3 inhibitor which exhibited potent anti-tumor and induced chemo- and radio-sensitivity in nasopharyngeal carcinoma. | [Definition]
ChEBI: Stattic is a member of the class of 1-benzothiophenes that is 1-benzothiophene-1,1-dioxide substituted at position 6 by a nitro group. Used as a radiosensitising agent for esophageal squamous cell carcinoma. It has a role as an antineoplastic agent, a STAT3 inhibitor and a radiosensitizing agent. It is a member of 1-benzothiophenes, a C-nitro compound and a sulfone. | [Biological Activity]
Small molecule inhibitor of STAT3. Inhibits binding of tyrosine-phosphorylated peptide motifs to STAT3 SH2 domain and inhibits STAT3 activation, dimerization and nuclear translocation. Displays selectivity over STAT1, STAT5, c-Myc/Max, Jun/Jun and Lck. Induces apoptosis in STAT3-dependent cancer cell lines. | [Biochem/physiol Actions]
Stattic (Stat3 three inhibitory compound) alters the SH2 domain of Stat3 and indirectly inhibits with phosphopeptide binding. It is readily transported across the cell membrane compared to other phosphopeptides.2 Stattic induces increased formation of ROS and negatively affects the cardiomyocyte mitochondrial function,3 and sensitizes nasopharyngeal carcinoma cells to chemoradiotherapy.4 | [Synthesis]
General procedure for the synthesis of 6-nitrobenzo[b]thiophene 1,1-dioxide from benzo[b]thiophene 1,1-dioxide: with reference to Example 118, nitric acid (10 mL) was slowly added dropwise to sulfuric acid (10 mL) at 0° C. The temperature was kept constant and the reaction mixture was stirred for 10 minutes. Subsequently, benzo[b]thiophene 1,1-dioxide (3.99 g) was slowly added to the above mixed acid solution at 0°C, and stirring was continued at the same temperature for 30 minutes. After completion of the reaction, the reaction mixture was slowly poured into ice water and extracted with ethyl acetate. The organic phases were combined and washed twice sequentially with water, saturated aqueous sodium bicarbonate solution and saturated saline, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to remove the solvent. The resulting residue was recrystallized by ethyl acetate-hexane mixed solvent to give light yellow solid 6-nitrobenzo[b]thiophene 1,1-dioxide (yield 4.26 g, 84% yield). The product was characterized by 1H-NMR (CDCl3): δ 7.00 (1H, d, J = 6.9 Hz), 7.33 (1H, dd, J = 1.2,6.9 Hz), 7.58 (1H, d, J = 8.4 Hz), 8.47 (1H, dd, J = 1.8,8.4 Hz), 8.55-8.57 (1H, m). | [storage]
+4°C | [References]
1) Schust et al. (2006), Stattic: a small molecule inhibitor of STAT3 activation and dimerization; Chem. Biol., 13 1235
2) Heidelberger et al. (2013), Investigation of the protein alkylation sites of the STAT3:STAT3 inhibitor Stattic by mass spectrometry; Bioorg. Med. Chem. Lett., 23 4719
3) Pan et al. (2013), Stat3 inhibitor Stattic exhibits potent anti-tumor activity and induces chemo- and radio-sensitivity in nasopharyngeal carcinoma; PLoS One, 8(1) e54565
4) Johnson et al. (2013), Small-molecules inhibitors of signal transducer and activator of transcription 3 protect against angiotensin II-induced vascular dysfunction and hypertension; Hypertension, 61 437 |
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| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
Sigma-Aldrich
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| Telephone: |
021-61415566 800-8193336 |
| Website: |
https://www.sigmaaldrich.cn |
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