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SML1999

Sigma-Aldrich

Sm4

≥98% (HPLC)

Sinonimo/i:

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

Formula empirica (notazione di Hill):
C19H16O3
Numero CAS:
365542-77-4
Peso molecolare:
292.33
Numero MDL:
MFCD12546734
Codice UNSPSC:
12352200
NACRES:
NA.77

Saggio

≥98% (HPLC)

Colore

white to beige

Solubilità

DMSO: 2 mg/mL, clear

Temperatura di conservazione

2-8°C

Stringa SMILE

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)
GGVFBUYNEPBFQT-UHFFFAOYSA-N

Azioni biochim/fisiol

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.).

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H315,H319,H335

Classi di pericolo

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

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

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Certificati d'analisi (COA)

Lot/Batch Number

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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
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
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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