5.31546
STAT3 Inhibitor XX, inS3-54
Synonym(s):
STAT3 Inhibitor XX, inS3-54, (E)-4-(3-(4-nitrobenzylidene)-2-oxo-5-phenyl-2,3-dihydro-1H-pyrrol-1-yl)benzoic acid
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About This Item
Empirical Formula (Hill Notation):
C24H16N2O5
CAS Number:
Molecular Weight:
412.39
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
Assay:
≥98% (HPLC)
Form:
powder
Storage condition:
OK to freeze, protect from light
assay
≥98% (HPLC)
Quality Segment
form
powder
potency
13.8 μM IC50
manufacturer/tradename
Calbiochem®
storage condition
OK to freeze, protect from light
color
orange
solubility
DMSO: 50 mg/mL
storage temp.
2-8°C
SMILES string
O=C1/C(C=C(C2=CC=CC=C2)N1C3=CC=C(C=C3)C(O)=O)=C/C4=CC=C(C=C4)[N+]([O-])=O
InChI
1S/C24H16N2O5/c27-23-19(14-16-6-10-21(11-7-16)26(30)31)15-22(17-4-2-1-3-5-17)25(23)20-12-8-18(9-13-20)24(28)29/h1-15H,(H,28,29)/b19-14+
InChI key
MSVZBBATVMKDKE-XMHGGMMESA-N
General description
A cell permeable compound that selectively binds to STAT3 and inhibits its DNA binding activity (IC₅₀ = 13.8 µM) and reduces the expression of STAT3 dependent genes.
A cell permeable pyrrolonyl benzoic acid derivative that selectively and non-covalently binds to STAT3 and inhibits its DNA binding activity in a dose and time dependent manner (IC50 = 13.8 µM after 29 hours incubation) and reduces the expression of STAT3 dependent genes (Cyclin D1, survivin, VEGF, MMP-2, MMP-9, and Twist) in A549 and MDA-MB-231 cells. However, it does not affect STAT3 dimerization or binding to the SH2 domain and has no effect on total STAT3 or basal level of Tyr705 phosphorylated STAT3. Preferentially induces apoptosis in cancer cells (A549 and MDA-MB-468) and inhibits their survival, but has much reduced effect on non-cancer IMR90 lung fibroblasts or MCF10A1 mammary epithelial cells. Shown to block cancer cell migration and invasion in a dose- and time-dependent manner.
Biochem/physiol Actions
Cell permeable: yes
Primary Target
STAT3
STAT3
Preparation Note
Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
Other Notes
Huang, W., et al. 2014. ACS Chem. Bio.9, 1188.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Disclaimer
Toxicity: Standard Handling (A)
Storage Class
11 - Combustible Solids
WGK
WGK 3
Flash Point (°F)
Not applicable
Flash Point (°C)
Not applicable
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