Butein Inhibits the tyrosine kinase activity of the EGF receptor and p60c-src

Butein (CAS 487-52-5)

Butein | CAS 487-52-5 is rated 5.0 out of 5 by 1.
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Synonym: 2',3,4,4'-Tetrahydroxychalcone
Application: Inhibits the tyrosine kinase activity of the EGF receptor and p60c-src
CAS Number: 487-52-5
Purity: ≥95%
Molecular Weight: 272.25
Molecular Formula: C15H12O5
* Refer to Certificate of Analysis for lot specific data (including water content).
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Butein is a plant polyphenol that acts as a specific protein tyrosine kinase inhibitor. Butein potently inhibits the tyrosine kinase activity of the EGF receptor (IC50 = 65 μM) and p60c-src (IC50 = 65 μM). The inhibition is competitive with respect to ATP and non-competitive with respect to the substrate. Butein is also a potent antioxidant and antiinflammatory agent which has been shown to inhibit glutathione reductase and rat liver GST (glutathione-S-transferase (IC50 = 9 μM)). Butein has been reported to activate sirtuins and promote the survival of eukaryotic cells. The Sirtuins, SIRT1-4 and SIRT7 are deacetylases relevant to histone modification. Butein directly inhibits IKK and suggested to also display inhibition towards PDE (c-AMP dependent PDE-IV). Also a potential CYP19 (Aromatase) inhibitor.


References

1. Zhang, K., et al., 1994. Inhibitory effects of plant polyphenols on rat liver glutathione S-transferases. Biochemical pharmacology. 47(11): 2063-8. PMID: 8010991
2. Zhang, K., et al., 1997. Inhibition of glutathione reductase by plant polyphenols. Biochemical pharmacology. 54(9): 1047-53. PMID: 9374426
3. Chan, S C., et al., 1998. Three new flavonoids and antiallergic, anti-inflammatory constituents from the heartwood of Dalbergia odorifera. Planta medica. 64(2): 153-8. PMID: 9525107
4. Yang, E B., et al., 1998. Butein, a specific protein tyrosine kinase inhibitor. Biochemical and biophysical research communications. 245(2): 435-8. PMID: 9571170
5. Howitz, Konrad T., et al., 2003. Small molecule activators of sirtuins extend Saccharomyces cerevisiae lifespan. Nature. 425(6954): 191-6. PMID: 12939617

Physical State :
Solid
Solubility :
Soluble in methanol, DMSO (>50 mg/ml), and toluene. Insoluble in water.
Storage :
Store at -20° C
Melting Point :
216.6-217.6° C
Boiling Point :
560.92° C at 760 mmHg (Predicted)
Density :
1.48 g/cm3 (Predicted)
Refractive Index :
n20D 1.75 (Predicted)
IC50 :
p60c-src: IC50 = 65 µM; Glutathione-S-transferase: IC50 = 9 µM (rat); Enoyl-[acyl-carrier-protein] reductase: IC50 = 30 µM (Escherichia coli K-12); Epidermal growth factor receptor erbB1: IC50 = 8 µM (human); Human immunodeficiency virus type 1 integrase: IC50 = 20 µM (Human immunodeficiency virus 1); Angiotensin-converting enzyme: IC50 = 0.73 µM (rabbit); Arachidonate 5-lipoxygenase: IC50 = 4.6 nM (rat)
Ki Data :
Enoyl-acyl-carrier protein reductase: Ki= 14 nM (Plasmodium falciparum)
pK Values :
pKa: 7.44
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
UD 5574135
PubChem CID :
5281222
MDL Number :
MFCD00017300
EC Number :
207-659-5
SMILES :
C1=CC(=C(C=C1/C=C/C(=O)C2=C(C=C(C=C2)O)O)O)O

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Butein  Product Citations

See how others have used Butein. Click on the entry to view the PubMed entry .

Citations 1 to 4 of 4 total

PMID: # 26676515  Woo, SM. et al. 2016. Mol Med Rep. 13: 1091-6.

PMID: # 25962638  Bai, X. et al. 2015. Oncology reports. 33: 3085-92.

PMID: # 24919544  Cho, SG. et al. 2014. J. Exp. Clin. Cancer Res. 33: 51.

PMID: # 24722292  Cioce, M. et al. 2014. Cell Death Dis. 5: e1167.

Citations 1 to 4 of 4 total
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Rated 5 out of 5 by from A decrease in Neu protein expression was A decrease in Neu protein expression was observed by WB in SK-BR-3 cells when treated with butein. -SCBT QC
Date published: 2015-04-27
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