STF 31 Chemical Properties

Density 

1.247±0.06 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

DMSO: soluble20mg/mL, clear

pka

11.28±0.50(Predicted)

form 

powder

color 

white to beige

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month.

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)

InChIKey

NGQPRVWTFNBUHA-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

46

WGK Germany 

3

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral

STF 31 Usage And Synthesis

Description

Glucose transporter 1 (Glut1) is an inducible carrier of pentoses and hexoses, including glucose. STF-31 is an inhibitor of Glut1 (IC₅₀ = ~1 μM) that blocks glucose uptake. It induces necrosis in cancer cells that lack the von Hippel-Lindau tumor suppressor gene, which overexpress Glut1. Although STF-31 binds Glut1, suggesting a direct effect, STF-31 also inhibits nicotinamide phosphoribosyltransferase, an enzyme that induces Glut1 expression. STF-31 is also toxic to human pluripotent stem cells (hPSCs) and can be used to selectively eliminate hPSCs from mixed cultures.

Uses

STF 31 is used in biological studies as pyridylanilinothiazoles and pyridylphenylsulfonyl benzamides scaffolds use to prepare affinity chromatoraphy reagents for cancer targeting. STF 31 is an inhibitor of GLUT1 which blocks glucose uptake.

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.

in vivo

IC 50

GLUT1: 1 μM (IC₅₀)

storage

Store at RT

References

[1] DENISE A. CHAN. Targeting GLUT1 and the Warburg Effect in Renal Cell Carcinoma by Chemical Synthetic Lethality[J]. Science Translational Medicine, 2011, 3 94. DOI:10.1126/scitranslmed.3002394
[2] DREW J. ADAMS. NAMPT Is the Cellular Target of STF-31-Like Small-Molecule Probes[J]. ACS Chemical Biology, 2014, 9 10: 2247-2254. DOI:10.1021/cb500347p
[3] PETER S. DRAGOVICH . Fragment-based design of 3-aminopyridine-derived amides as potent inhibitors of human nicotinamide phosphoribosyltransferase (NAMPT)[J]. Bioorganic & Medicinal Chemistry Letters, 2014, 24 3: Pages 954-962. DOI:10.1016/j.bmcl.2013.12.062
[4] DOMINIK KRAUS. Targeting glucose transport and the NAD pathway in tumor cells with STF-31: a re-evaluation.[J]. Cellular Oncology, 2018, 41 5: 485-494. DOI:10.1007/s13402-018-0385-5

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