SML1999
Sm4
≥98% (HPLC)
Synonym(s):
2-Hydroxy-6-(2-(naphthalen-2-yl)ethyl)benzoic acid, 2-Hydroxy-6-[2-(2-naphthyl)ethyl]benzoic acid
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About This Item
Empirical Formula (Hill Notation):
C19H16O3
CAS Number:
Molecular Weight:
292.33
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
Assay:
≥98% (HPLC)
assay
≥98% (HPLC)
color
white to beige
solubility
DMSO: 2 mg/mL, clear
storage temp.
2-8°C
SMILES string
OC1=C(C(O)=O)C(CCC2=CC3=C(C=CC=C3)C=C2)=CC=C1
InChI
1S/C19H16O3/c20-17-7-3-6-15(18(17)19(21)22)11-9-13-8-10-14-4-1-2-5-16(14)12-13/h1-8,10,12,20H,9,11H2,(H,21,22)
InChI key
GGVFBUYNEPBFQT-UHFFFAOYSA-N
Biochem/physiol Actions
Orally active SOX18 inhibitor with in vivo efficacy against zebrafish larvae vascular formation and breast cancer tumor lymphangiogenesis in mice.
Sm4 is an orally active SOX18 inhibitor (IC50 = 5,2 μM; COS-7 reporter assay) that directly targets SOX18 HMG domain and preferentially disrupts SOX18 interaction with a subset of binding partners (IC50 = 3.3 μM/SOX18-SOX18, 15.8 μM/SOX18-DDX17, 42.3 μM/SOX18-RBPJ, 65.9 μM/SOX18-RBPJ; IC50 ≥780 μM against SOX9 dimer or SOX18 interaction with MEF2C, NR2F2, TRIM28, ESR1), while affecting HMG-dependent DNA binding in a less potent and non-SOX18-selective manner (IC50 ∼200-220 μM for SOX15/18, IC50 ∼270-310 μM for SOX2/6/9/11). Sm4 selectively affects SOX18 target genes transcription over 7 other transcription factors by genome-wide ChIP-seq analysis as well as displays in vivo efficacy against vascular formation in zebrafish larvae (1-2 μM) and induces tumor metastasis by inhibiting angiogenesis/lymphangiogenesis in a murine model of breast cancer (25 mg/kg/d p.o.).
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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