General description
A cell-permeable, reversible, substrate competitive inhibitor of protein tyrosine kinases, including autophosphorylation of epidermal growth factor receptor kinase (IC50 = 2.6 µM). The inhibition is competitive with respect to ATP and non-competitive with respect to the phosphate acceptor. Inhibits tumor cell proliferation and induces tumor cell differentiation. Inhibits exogenous substrate phosphorylation by EGFR kinase and pp60v-src with similar potencies (IC50 = 20-25 µM). Has only a trivial effect on PKC and PKA (IC50 >350 µM). Produces cell cycle arrest and apoptosis in Jurkat T-leukemia cells. Prevents anti-CD3 monoclonal antibody-induced thymic apoptosis. Also inhibits topoisomerase II activity in vitro. Blocks oxidative DNA damage in vitro.
Biochem/physiol Actions
Cell permeable: yes
Primary Target
EGFR kinase
Product does not compete with ATP.
Reversible: yes
Target IC50: 2.6 µM against autophosphorylation of epidermal growth factor receptor kinase
Other Notes
Constantinou, A., and Huberman, E. 1995. Proc. Soc. Exp. Biol. Med. 208, 109.
Wei, H., et al. 1995. Proc. Soc. Exp. Biol. Med. 208, 124.
Wei, H., et al. 1995. Carcinogenesis17, 73.
Kobayashi, S., et al. 1994. J. Biol. Chem.269, 9011.
Migita, K., et al. 1994. J. Immunol.153, 3457.
Spinozzi, F., et al. 1994. Leuk. Res.18, 431.
Dhar, A., et al. 1990. Mol. Pharmacol.37, 519.
Hill, T.D., et al. 1990. Science248, 1660.
Dean, N.M., et al. 1989. Biochem. Biophys. Res. Commun.165, 795.
Akiyama, T., et al. 1987. J. Biol. Chem.262, 5592.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Disclaimer
Toxicity: Standard Handling (A)
| Quality Segment | 100 |
| description | Merck USA index - 14, 4391 |
| assay | ≥95% (HPLC) |
| form | solid |
| manufacturer/tradename | Calbiochem® |
| storage condition | OK to freeze,protect from light |
| color | white |
| solubility | DMSO: 200 mg/mL |
| shipped in | ambient |
| storage temp. | −20°C |
| SMILES string | [o]1c2c([c](c(c1)c3ccc(cc3)O)=O)c(cc(c2)O)O |
| InChI | 1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H |
| InChI key | TZBJGXHYKVUXJN-UHFFFAOYSA-N |
