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Submit ReviewGenistein
Description: EGFR kinase inhibitor. Also estrogen and PPARγ ligand
Chemical Name: 5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
Purity: ≥98% (HPLC)
Biological Activity for Genistein
Genistein is a phytoestrogen with a wide range of biological actions. Genistein inhibits protein tyrosine kinases including epidermal growth factor receptor kinase, binds to PPARγ and estrogen receptors and acts as an agonist at GPER. Genistein inhibits aggregation and fibrilization of Aβ42 and amylin37 (hiAPP). In Huntington's disease fibroblast cells, Genistein reduces intracellular mutant huntingtin (mHTT) aggregates and induces degradation of mHTT; in a cellular model of Huntington's disease, Genistein corrects the mutant phenotype through stimulation of autophagy.
Compound Libraries for Genistein
Genistein is also offered as part of the Tocriscreen 2.0 Max. Find out more about compound libraries available from Tocris.
Technical Data for Genistein
| M. Wt | 270.24 |
| Formula | C15H10O5 |
| Storage | Desiccate at -20°C |
| Purity | ≥98% (HPLC) |
| CAS Number | 446-72-0 |
| PubChem ID | 5280961 |
| InChI Key | TZBJGXHYKVUXJN-UHFFFAOYSA-N |
| Smiles | OC1=CC=C(C=C1)C1=COC2=C(C(O)=CC(O)=C2)C1=O |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for Genistein
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 100 |
Preparing Stock Solutions for Genistein
The following data is based on the product molecular weight 270.24. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 3.7 mL | 18.5 mL | 37 mL |
| 5 mM | 0.74 mL | 3.7 mL | 7.4 mL |
| 10 mM | 0.37 mL | 1.85 mL | 3.7 mL |
| 50 mM | 0.07 mL | 0.37 mL | 0.74 mL |
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Product Datasheets for Genistein
References for Genistein
References are publications that support the biological activity of the product.
Akiyama et al (1987) Genistein, a specific inhibitor of tyrosine-specific protein kinases. J.Biol.Chem. 262 5592 PMID: 3106339
Dang et al (2003) Peroxisome proliferator-activated receptor γ (PPARγ) as a molecular target for the soy phytoestrogen genistein. J.Biol.Chem. 278 962 PMID: 12421816
Linassier et al (1990) Mechanisms of action in NIH-3T3 cells of genistein, an inhibitor of EGF receptor tyrosine kinase activity. Biochem.Pharmacol. 39 187 PMID: 2153378
Migita et al (1994) Prevention of anti-CD3 monoclonal antibody-induced thymic apoptosis by protein tyrosine kinase inhibitors. J.Immunol. 153 3457 PMID: 7523495
Merck Index 12 4395
Ren et al (2018) Genistein: A Dual Inhibitor of Both Amyloid β and Human Islet Amylin Peptides. ACS.Chem.Neurosci. 9 1215 PMID: 29432676
Pierzynowska et al (2019) Genistein induces degradation of mutant huntingtin in fibroblasts from Huntington's disease patients. Metab.Brain Dis. 34 PMID: 30850940
If you know of a relevant reference for Genistein, please let us know.
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Keywords: Genistein, Genistein supplier, PPARγ, PPARgamma, ligands, estrogen, receptor, EGFR, inhibitors, inhibits, GPR30, agonists, tyrosine, kinase, Estrogen, Peroxisome, Proliferator-activating, Receptors, PPAR, Epidermal, Growth, Factors, ErbB, Her, Receptor, Tyrosine, Kinases, RTKs, ER, ERR, GPER, huntingtons, muta, and, Related, (GPER), 1110, Tocris Bioscience
10 Citations for Genistein
Citations are publications that use Tocris products. Selected citations for Genistein include:
Li et al (2011) Synergistic activation of DA D1 and TrkB receptors mediate gain control of synaptic plasticity in the basolateral amygdala. PLoS One 6 e26065 PMID: 22022509
Accardi et al (2015) α6-Containing GABAA Receptors Are the Principal Mediators of Inhibitory Synapse Strengthening by Ins in Cerebellar Granule Cells. J Neurosci 35 9676 PMID: 26134650
Bigford et al (2012) 5-Hydroxytryptamine 5HT2C receptors form a protein complex with N-MthD.-aspartate GluN2A subunits and activate phosphorylation of Src protein to modulate motoneuronal depolarization. J Biol Chem 287 11049 PMID: 22291020
Olianas et al (2016) The GABAB positive allosteric modulators CGP7930 and GS39783 stimulate ERK1/2 signalling in cellslacking functional GABAB receptors European Journal of Pharmacology 794 135 PMID: 27876620
Mansouri-Attia et al (2014) Soy promotes juvenile granulosa cell tumor development in mice and in the human granulosa cell tumor-derived COV434 cell line. Biol Reprod 91 100 PMID: 25165122
Kim et al (2018) Estrogen modulates serotonin effects on vasoconstriction through Src inhibition. Exp Mol Med 50 167 PMID: 30559345
Liu et al (2015) A dual role for NOTCH signaling in joint cartilage maintenance and osteoarthritis. Sci Signal 8 ra71 PMID: 26198357
Alao et al (2006) Role of glycogen synthase kinase 3 β (GSK3β) in mediating the cytotoxic effects of the histone deacetylase inhibitor trichostatin A (TSA) in MCF-7 breast cancer cells. Neurotox Res 5 40 PMID: 17018141
Rojas et al (2007) Protein kinase C dependent inhibition of the heteromeric Kir4.1-Kir5.1 channel. Biochim Biophys Acta 1768 2030 PMID: 17585871
Melis et al (2008) Endogenous fatty acid ethanolamides suppress nicotine-induced activation of mesolimbic DA neurons through nuclear receptors. J Neurosci 28 13985 PMID: 19091987
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