G6776
Sigma

Genistein

from Glycine max (soybean), ~98% (HPLC)

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Synonym

4′,5,7-Trihydroxyisoflavone

5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

Molecular Formula

C₁₅H₁₀O₅

Molecular Weight

270.24

CAS Number

446-72-0

Beilstein Registry Number

263823

MDL number

MFCD00016952

PubChem Substance ID

24895273

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Descriptions

Biochem/physiol Actions

Inhibitor of tyrosine protein kinase; competitive inhibitor of ATP in other protein kinase reactions. Antiangiogenic agent, down-regulates the transcription of genes involved in controlling angiogenesis.

Properties

biological source

from Glycine max (soybean)

assay

~98% (HPLC)

solubility

DMSO: soluble

ethanol: soluble

Gene Information

human ... AKT1(207), CYP19A1(1588), EGFR(1956), ESR1(2099), ESR2(2100)

rat ... Adora1(29290), Adora2a(25369), Ar(24208)

mouse ... Esr1(13982), Hexa(15211)

storage temp.

−20°C

References

Reference

Akiyama, T., et al., Genistein, a specific inhibitor of tyrosine-specific protein kinases. J. Biol. Chem. 262, 5592-5595, (1987)

Hakansson, G., and Allen, J.F., Histidine and tyrosine phosphorylation in pea mitochondria: evidence for protein phosphorylation in respiratory redox signalling. FEBS Lett. 372, 238-242, (1995)

Igarashi, M., and Komiya, Y., Tyrosine phosphorylation and immunodetection of vinculin in growth cone particle (GCP) fraction and in GCP-cytoskeletal subfractions. J. Neurosci. Res. 30, 266-274, (1991)

Li, Y., and Sarkar, F., Down-regulation of invasion and angiogenesis-related genes identified by cDNA microarray analysis of PC3 prostate cancer cells treated with genistein. Cancer Lett. 186, 157, (2002)

Wietrzyk, J., et al., Antiangiogenic and antitumour effects in vivo of genistein applied alone or combined with cyclophosphamide. Anticancer Res. 12, 3893-3896, (2001)

Huang J., et al., Genistein inhibits protein histidine kinase. J. Biol. Chem. 267, 15511-15515, (1992)

O'Dell, T.J., et al., Long-term potentiation in the hippocampus is blocked by tyrosine kinase inhibitors. Nature 353, 558-560, (1991)

Merck

Merck 13,4402

Beilstein

Beil. 18,V,4,594

Safety

Hazard Codes

Risk Statements

36/38

Safety Statements

WGK Germany