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AdipoGen Life Sciences

Genistein

CHF 28.00
In stock
AG-CN2-0427-M01010 mgCHF 28.00
AG-CN2-0427-M05050 mgCHF 40.00
AG-CN2-0427-M250250 mgCHF 80.00
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Fax  +41 61 926 6049
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Product Details
Synonyms NSC 36586; Baichanin A; Differenol A; 4',5,7-Trihydroxyisoflavone; 5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
Product Type Chemical
Properties
Formula

C15H10O5
MW 270.2
Merck Index 14: 4391
CAS 446-72-0
RTECS NR2392000
Source/Host Chemicals Synthetic.
Purity Chemicals ≥99%
Appearance White to off-white solid.
Solubility Soluble in DMSO; slightly soluble in ethanol. Insoluble in water.
InChi Key TZBJGXHYKVUXJN-UHFFFAOYSA-N
Smiles OC1=CC=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Keep cool and dry.
Protect from light.
Use/Stability Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
Description
  • Cell-permeable, reversible, substrate competitive tyrosine kinase inhibitor (including EGFR phosphorylation), implicated in almost all cell growth and proliferation signal cascades [1].
  • Inhibitor of mammalian DNA topoisomerase II [2].
  • Anticancer agent, inducing cell cycle arrest and apoptosis [3].
  • Antiangiogenic agent, down-regulates the transcription of genes involved in controlling angiogenesis [12].
  • Binds estrogen receptor β. Can increase the rate of growth of some ER expressing breast cancers [4, 10].
  • Potent α-glucosidase inhibitor [5].
  • Anthelmintic [6].
  • Anti-diabetic. Activates nuclear receptors, oestrogen receptors and peroxisome proliferator-activated receptors (all PPAR isoforms) and it inhibits various enzyme activities [7, 8, 14].
  • Inhibitor of GLUT4-mediated glucose uptake in 3T3-L1 adipocytes [9].
  • Stimulator of autophagy vacuolization [12].
  • Antioxidant [13].
  • TRAIL sensitizer [15].
  • Acts as an agonist at the GPR30 receptor [16].
  • MALT1 inhibitor [17]
  • DNA methyltransferase inhibitor [18].
  • Genistein exhibits synergistic antibacterial effects on MRSA [19].
Product References
  1. Genistein, a specific inhibitor of tyrosine-specific protein kinases: T. Akiyama, et al.; J. Biol. Chem. 262, 5592 (1987)
  2. Inhibitory effects of the tyrosine kinase inhibitor genistein on mammalian DNA topoisomerase II: J. Markovits, et al.; Cancer Res. 49, 5111 (1989)
  3. Genistein inhibition of the growth of human breast cancer cells: independence from estrogen receptors and the multi-drug resistance gene: G. Peterson & S. Barnes; BBRC 179, 661 (1991)
  4. Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta: G.G. Kuiper, et al.; Endocrinology 139, 4252 (1998)
  5. Genistein, a soy isoflavone, is a potent alpha-glucosidase inhibitor: DS. Lee & SH. Lee; FEBS Lett. 501, 84 (2001)
  6. Anthelmintic efficacy of Flemingia vestita: genistein-induced effect on the activity of nitric oxide synthase and nitric oxide in the trematode parasite, Fasciolopsis buski: P.K. Kar, et al.; Parasitol. Int. 51, 249 (2002)
  7. Soy isoflavones exert antidiabetic and hypolipidemic effects through the PPAR pathways in obese Zucker rats and murine RAW 264.7 cells: O. Mezei, et al.; J. Nutr. 133, 1238 (2003)
  8. Peroxisome proliferator-activated receptor gamma (PPARgamma ) as a molecular target for the soy phytoestrogen genistein: Z.C. Dang, et al.; J. Biol. Chem. 278, 962 (2003)
  9. Genistein directly inhibits GLUT4-mediated glucose uptake in 3T3-L1 adipocytes: M. Bazuine, et al.; BBRC 326, 511 (2005)
  10. Genistein stimulates growth of human breast cancer cells in a novel, postmenopausal animal model, with low plasma estradiol concentrations Y.H. Ju, et al.; Carcinogenesis 27, 1292 (2006)
  11. Phytochemical genistein in the regulation of vascular function: new insights: H. Si & D. Liu; Curr. Med. Chem. 14, 2581 (2007)
  12. Diet, autophagy, and cancer: a review: K. Singletary & J. Milner; Cancer Epidemiol. Biomarkers Prev. 17, 1596 (2008) (Review)
  13. Comparison of flavonoids and isoflavonoids as antioxidants: RM. Han, et al.; J. Agric. Food Chem. 57, 3780 (2009)
  14. Dose-dependent effects of soy phyto-oestrogen genistein on adipocytes: mechanisms of action: Z.C. Dang; Obes. Rev. 10, 342 (2009) (Review)
  15. Novel HTS strategy identifies TRAIL-sensitizing compounds acting specifically through the caspase-8 apoptotic axis: D. Finlay, et al.; PLoS One 5, e13375 (2010)
  16. Genistein regulates the IL-1 beta induced activation of MAPKs in human periodontal ligament cells through G protein-coupled receptor 30: L.J. Luo, et al.; Arch. Biochem. Biophys. 522, 9 (2012)
  17. MALT1 small molecule inhibitors specifically suppress ABC-DLBCL in vitro and in vivo: L. Fontan, et al.; Cancer Cell 22, 812 (2012)
  18. DNA methyltransferase-1 inhibitors as epigenetic therapy for cancer: V. Singh, et al.; Curr. Cancer Drug Targets 13, 379 (2013)
  19. Flavonoids from Sophora moorcroftiana and their synergistic antibacterial effects on MRSA: SY. Wang, et al.; Phytother. Res. 28, 1071 (2014)
  20. Anti-estrogenic and anti-aromatase activities of citrus peels major compounds in breast cancer: D.M. El-Kersh, et al.; Nature Sci. Rep. 11, 7121 (2021)
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