General description
A cell-permeable isoflavone compound that acts as a potent and competitive inhibitor of fructose-2,6-bisphosphatase 3 (PFKFB3; IC50 = 670 nM; Ki = 240 nM). Directly docks into the Fru-6-P binding pocket of PFKFB3 and down-regulates Fru-2,6-BP levels (40% decrease in 48 h in HeLa cells) resulting in reduced glycolysis and lactate production. Shown to diminish the proliferation of HCT-116 human adenocarcinoma cells (GI50 = 8.2 µM) and inhibit HeLa cells colony formation on soft agar (~79% reduction at 25 µM). Induces apoptotic (~25 µM) and necrotic (~50 µM) cell death depending on the level of ATP depletion. Also reported to increase autophagy in HCT-116 cells as evidenced by an increase in LC3-II levels and a decrease in p62 levels.
Please note that the molecular weight for this compound is batch-specific due to variable water content.
Biochem/physiol Actions
Cell permeable: yes
Reversible: yes
Packaging
Packaged under inert gas
Other Notes
Klarer, A. C., et al. 2014. Cancer Metab.2, 2.
Seo, M., et al. 2011. PLoS ONE6, e24179.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Disclaimer
Toxicity: Regulatory Review (Z)
| assay | ≥98% (HPLC) |
| Quality Segment | 100 |
| form | powder |
| potency | 670 nM IC50 |
| manufacturer/tradename | Calbiochem® |
| storage condition | OK to freeze,protect from light |
| color | off-white |
| solubility | DMSO: 100 mg/mL |
| storage temp. | 2-8°C |
| SMILES string | [o]1c2c([c](c(c1)c3ccc(cc3)O)=O)ccc(c2O)O |
| InChI | 1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-15-10(13(11)18)5-6-12(17)14(15)19/h1-7,16-17,19H |
| InChI key | BMZFZTMWBCFKSS-UHFFFAOYSA-N |
