G6649
Sigma

Genistein

synthetic, ≥98% (HPLC), powder

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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

24278036

EG/EC Number

207-174-9

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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

synthetic

assay

≥98% (HPLC)

form

powder

color

off-white

solubility

DMSO: soluble

ethanol: soluble

Gene Information

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

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

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

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)

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

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)

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

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

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)

Merck

Merck 13,4402

Beilstein

Beil. 18,V,4,594

Safety

Safety Statements

22-24/25

WGK Germany

RTECS

NR2392000