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SML1108

Sigma-Aldrich

STF-31

≥98% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C23H25N3O3S
CAS Number:
724741-75-7
Molecular Weight:
423.53
MDL number:
MFCD04153828
UNSPSC Code:
12352200
PubChem Substance ID:
329825483
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

−20°C

SMILES string

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)

InChI key

NGQPRVWTFNBUHA-UHFFFAOYSA-N

Application

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

Biochem/physiol Actions

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.

Features and Benefits

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
Prahlad V Raninga et al.
Theranostics, 10(12), 5259-5275 (2020-05-07)
Purpose: Lacking effective targeted therapies, triple-negative breast cancer (TNBCs) is highly aggressive and metastatic disease, and remains clinically challenging breast cancer subtype to treat. Despite the survival dependency on the proteasome pathway genes, FDA-approved proteasome inhibitors induced minimal clinical response
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
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