10798
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10798
Sigma
Apigenin
BioChemika, ≥95.0% (HPLC)
| Synonym: | 4′,5,7-Trihydroxyflavone |
| CAS Number: | 520-36-5 |
| Linear Formula: | C15H10O5 |
| Molecular Weight: | 270.24 |
| Beilstein Registry Number: | 262620 |
| EC Number: | 208-292-3 |
| MDL number: | MFCD00006831 |
| PubChem Substance ID: | 24846790 |
Description
| Biochem/physiol Actions | A plant flavonoid that has been found to inhibit cell proliferation by arresting the cell cycle at the G2/M phase. Inhibition of growth through cell cycle arrest and induction of apoptosis appear to be related to induction of p53. Inhibitory effects on tumor promotion may also be due to inhibition of kinase activity and the resulting suppression of oncogene expression. It has also been reported to inhibit topoisomerase I catalyzed DNA religation and enhance gap junctional intercellular communication. |
| Other Notes | Inhibitor of human estrogen synthetase1 |
Properties
| product line | BioChemika |
| assay | ≥95.0% (HPLC) |
| total impurities | ~2% water |
| mp | >300 °C(lit.) |
| Gene Information | human ... ADORA3(140), CDC2(983), CDK5(1020), CDK6(1021), CYP1A2(1544), ESR1(2099), ESR2(2100), GSK3A(2931) |
| rat ... Adora1(29290), Adora2a(25369), Il4(287287), Tnf(24835) | |
| mouse ... Hexa(15211) | |
| storage temp. | −20°C |
Safety
| Personal Protective Equipment | dust mask type N95 (US), Eyeshields, Gloves |
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 26-36 |
| WGK Germany | 3 |
| RTECS | LK9276000 |
References
| Cited Reference | 1. J.T. Kellis, L.E. Vickery Science 225, 1032, (1984) Abstract |
| reference | Sato, F., et al., Apigenin induces morphological differentiation and G2-M arrest in rat neuronal cells. Biochem. Biophys. Res. Commun. 204, 578-584, (1994) |
| Plaumann, B., et al., Flavonoids activate wild-type p53. Oncogene 13, 1605-1614, (1996) | |
| Way, T.D., et al., Degradation of HER2/neu by apigenin induces apoptosis through cytochrome c release and caspase-3 activation in HER2/neu-overexpressing breast cancer cells. FEBS Lett. 579, 145-152, (2005) | |
| Huang, Y.T., et al., Inhibition of protein kinase C and proto-oncogene expression in NIH 3T3 cells by apigenin. Eur. J. Cancer 32A, 146-151, (1996) | |
| Snyder, R.D., and Gillies, P.J., Evaluation of the clastogenic, DNA intercalative, and topoisomerase II-interactive properties of bioflavonoids in Chinese hamster V79 cells. Environ. Mol. Mutagen. 40, 266-276, (2002) | |
| Czyz, J., et al., Hierarchy of carcinoma cell responses to apigenin: gap junctional coupling versus proliferation. Oncol. Rep. 11, 739-744, (2004) | |
| Merck | Merck 13,737 |
| Beilstein | Beil. 18,V,4,574 |
