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Merck
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Documentos

SML1999

Sigma-Aldrich

Sm4

≥98% (HPLC)

Sinónimos:

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

Fórmula empírica (notación de Hill):
C19H16O3
Número de CAS:
365542-77-4
Peso molecular:
292.33
MDL number:
MFCD12546734
UNSPSC Code:
12352200
NACRES:
NA.77

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

Biochem/physiol Actions

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.).

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Jeroen Overman et al.
eLife, 6 (2017-02-01)
Pharmacological targeting of transcription factors holds great promise for the development of new therapeutics, but strategies based on blockade of DNA binding, nuclear shuttling, or individual protein partner recruitment have yielded limited success to date. Transcription factors typically engage in
Frank Fontaine et al.
Cell chemical biology, 24(3), 346-359 (2017-02-07)
Pharmacological modulation of transcription factors (TFs) has only met little success over the past four decades. This is mostly due to standard drug discovery approaches centered on blocking protein/DNA binding or interfering with post-translational modifications. Recent advances in the field
Olga Rodak et al.
International journal of molecular sciences, 24(14) (2023-07-29)
The transcription factor SOX18 has been shown to play a crucial role in lung cancer progression and metastasis. In this study, we investigated the effect of Sm4, a SOX18 inhibitor, on cell cycle regulation in non-small cell lung cancer (NSCLC)
Sreeman K Mamidyala et al.
Bioorganic & medicinal chemistry letters, 23(6), 1667-1670 (2013-02-19)
Anacardic acid derivatives exhibit a broad range of biological activities. In this report, an efficient method for the synthesis of anacardic acid derivatives was explored, and a small set of salicylic acid variants synthesised retaining a constant hydrophobic element (a

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