Sm4

Name: Sm4
Brand: SIGMA

≥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:

365542-77-4

Molecular Weight:

292.33

UNSPSC Code:

12352200

NACRES:

NA.77

MDL number:

MFCD12546734

Assay:

≥98% (HPLC)

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Properties

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

Description

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.).