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SML1108

Sigma-Aldrich

STF-31

≥98% (HPLC)

Synonyme(s) :

4-[[[[4-(1,1-Dimethylethyl)phenyl]sulfonyl]amino]methyl]-N-3-pyridinyl-benzamide

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About This Item

Formule empirique (notation de Hill):
C23H25N3O3S
Numéro CAS:
724741-75-7
Poids moléculaire :
423.53
Numéro MDL:
MFCD04153828
Code UNSPSC :
12352200
ID de substance PubChem :
329825483
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 20 mg/mL, clear

Température de stockage

−20°C

Chaîne SMILES 

O=C(NC1=CN=CC=C1)C2=CC=C(CNS(=O)(C3=CC=C(C(C)(C)C)C=C3)=O)C=C2

InChI

1S/C23H25N3O3S/c1-23(2,3)19-10-12-21(13-11-19)30(28,29)25-15-17-6-8-18(9-7-17)22(27)26-20-5-4-14-24-16-20/h4-14,16,25H,15H2,1-3H3,(H,26,27)

Clé InChI

NGQPRVWTFNBUHA-UHFFFAOYSA-N

Application

STF-31 has been used in glucose transporter 1 (GLUT1) inhibition.

Actions biochimiques/physiologiques

STF-31 selectively inhibits the glucose transporter GLUT1 and selectively impairs cancer cell growth of kidney and other types of cancer cells that lack the von Hippel-Lindau (VHL) tumor suppressor protein. Inactivation of VHL increases the activity of hypoxia-inducible factor transcription factor HIF, which in turn stimulates the transcription of genes involved in glucose metabolism, including the GLUT1 gene. VHL-deficient cancer cells, which include about 80% of renal cell carcinomas, are dependent on the high affinity GLUT1 transporter and aerobic glycolysis for ATP production. STF-31 binds directly to the GLUT1 transporter, blocking glucose uptake, resulting in necrosis in VHL-deficient cancer cells, but not in normal cells or cancer cells with intact VHL.

Caractéristiques et avantages

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302

Classification des risques

Acute Tox. 4 Oral

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Chaoyi Zhang et al.
The Journal of endocrinology, 246(2), 109-122 (2020-06-03)
Adropin plays a role in the maintenance of energy homeostasis, insulin resistance prevention, and impaired glucose tolerance. However, the molecular mechanisms by which adropin affects hepatic glucose and lipid metabolism in vitro are not entirely understood. This study intended to
Hypoxia increases glucose transporter 1 expression in bovine corpus luteum at the early luteal stage
Nishimura R, et al.
The Journal of Veterinary Medical Science, 79(11), 1878-1883 (2017)
Jun Zhang et al.
Oncogene, 38(24), 4669-4684 (2019-02-13)
EBV infection of preinvasive nasopharyngeal epithelium is believed to be an initiation step during pathogenesis of nasopharyngeal carcinoma (NPC), but the mechanisms remain poorly understood. Here we report a novel mechanism driving NPC metastasis through the EBV-encoded LMP1-mediated metabolic reprogramming
Ryo Nishimura et al.
The Journal of veterinary medical science, 79(11), 1878-1883 (2017-10-20)
A major role of the corpus luteum (CL) is to produce progesterone (P4). The CL has immature vasculature shortly after ovulation, suggesting it exists under hypoxic conditions. Hypoxia-inducible factor-1 (HIF1) induces the expression of glucose transporter 1 (GLUT1). To clarify
Mª Carmen Ocaña et al.
Scientific reports, 10(1), 6132-6132 (2020-04-11)
The synthetic compound fasentin has been described as a modulator of GLUT-1 and GLUT-4 transporters, thus inhibiting glucose uptake in some cancer cells. Endothelial glucose metabolism has been recently connected to angiogenesis and it is now an emerging topic in
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