178278

Apigenin

Induces the reversion of transformed phenotypes of v-H-ras-transformed NIH 3T3 cells at low concentration (12.5 µM).

• Synonym(s): Apigenin, 4ʹ,5,7-Trihydroxyflavone
• Empirical Formula (Hill Notation): C₁₅H₁₀O₅
• CAS Number: 520-36-5
• Molecular Weight: 270.24
• UNSPSC Code: 12352212
• NACRES: NA.77
• MDL number: MFCD00006831
• Assay: ≥98% (HPLC)
• Form: crystalline solid
• Storage condition: OK to freeze

Properties

• Quality Segment: 100
• description: Merck USA index - 14, 730
• assay: ≥98% (HPLC)
• form: crystalline solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze
• color: yellow
• solubility: hot ethanol: 1 mg/mL, DMSO: 10 mg/mL
• shipped in: ambient
• storage temp.: 2-8°C
• SMILES string: [o]1c2c([c](cc1c3ccc(cc3)O)=O)c(cc(c2)O)O
• InChI: 1S/C15H10O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-7,16-18H
• InChI key: KZNIFHPLKGYRTM-UHFFFAOYSA-N

Description

General description

A plant flavonoid that reverses the transformed phenotypes of various ras-transformed cells, apparently due to inhibition of mitogen activated protein (MAP) kinase-associated signal transduction pathways. Treatment of v-H-ras-transformed NIH 3T3 cells with apigenin (12.5 µM) has been shown to induce dephosphorylation of p44^mapk and reduction in MAP kinase activity. Has also been reported to inhibit the proliferation of malignant tumor cells by G₂/M arrest and to induce morphological differentiation.

Induces the reversion of transformed phenotypes of v-H-ras-transformed NIH 3T3 cells at low concentration (12.5 µM). This finding has been attributed to the inhibition of MAP kinase activity. Inhibits the proliferation of malignant tumor cells by G₂/M arrest and induces morphological differentiation.

Biochem/physiol Actions

Cell permeable: no

Primary Target
MAP kinase

Product does not compete with ATP.

Reversible: no

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). DMSO stock solutions are stable for up to 4 months at -20°C.

Other Notes

Kuo, M.L., and Yang, N.C. 1995. Biochem. Biophys. Res. Commun.212, 767.
Chaumontet, C., et al. 1994. Carcinogenesis 15, 2325.
Kuo, M.L., et al. 1994. Cancer Lett.87, 91.
Sato, F., et al. 1994. Biochem. Biophys. Res. Commun.204, 578.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Irritant (B)

Safety Information

• Storage Class: 11 - Combustible Solids
• WGK: WGK 3