Plumbagin
Biological Activity
Anticancer agent. Induces G2/M cell cycle arrest and apoptosis in A549 cells through JNK-dependent p53 Ser15 phosphorylation; inhibits A549 and MDA-MD-231 tumour xenograft growth in nude mice. Promotes autophagic cell death in MDA-MB-231 and MCF-7 cells and inhibits Akt/mTOR signaling. Induces intracellular ROS generation in a PI 5-kinase-dependent manner. Also inhibits p300-mediated acetylation of p53.
Technical Data
| M. Wt | 188.18 |
| Formula | C11H8O3 |
| Storage | Store at -20°C |
| Purity | ≥98% (HPLC) |
| CAS Number | 481-42-5 |
| PubChem ID | 10205 |
| InChI Key | VCMMXZQDRFWYSE-UHFFFAOYSA-N |
| Smiles | CC2=CC(C1=C(C2=O)C=CC=C1O)=O |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 18.82 | 100 | |
| ethanol | 9.41 | 50 |
Preparing Stock Solutions
The following data is based on the product molecular weight 188.18. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 5.31 mL | 26.57 mL | 53.14 mL |
| 5 mM | 1.06 mL | 5.31 mL | 10.63 mL |
| 10 mM | 0.53 mL | 2.66 mL | 5.31 mL |
| 50 mM | 0.11 mL | 0.53 mL | 1.06 mL |
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Product Datasheets
References
References are publications that support the biological activity of the product.
Hsu et al (2006) Plumbagin (5-hydroxy-2-methyl-1,4-napthoquinone) induces apoptosis and cell cycle arrest in A549 cells through p53 accumulation via c-Jun NH2-terminal kinase mediated phosphorylation at serine 15 in vitro and in vivo. J.Pharmacol.Exp.Ther. 318 484 PMID: 16632641
Kuo et al (2006) Plumbagin induces G2-M arrest and autophagy by inhibiting the AKT/mammalian target of rapamycin pathway in breast cancer cells. Mol.Cancer Ther. 5 3209 PMID: 17172425
Lee et al (2012) The natural anticancer agent plumbagin induces potent cytotoxicity in MCF-7 human breast cancer cells by inhibiting a PI-5 kinase for ROS generation. PLoS One. 7 e45023 PMID: 23028742
Ravindra et al (2009) Inhibition of lysine acetyltransferase KAT3B/p300 activity by a naturally occurring hydroxynaphthoquinone, plumbagin. J.Biol.Chem. 284 24453 PMID: 19570987
If you know of a relevant reference for Plumbagin, please let us know.
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Literature in this Area
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Cancer Research Product Guide
A collection of over 750 products for cancer research, the guide includes research tools for the study of:
- Cancer Metabolism
- Epigenetics in Cancer
- Receptor Signaling
- Cell Cycle and DNA Damage Repair
- Angiogenesis
- Invasion and Metastasis
Cell Cycle & DNA Damage Repair Poster
In normal cells, each stage of the cell cycle is tightly regulated, however in cancer cells many genes and proteins that are involved in the regulation of the cell cycle are mutated or over expressed. Adapted from the 2015 Cancer Product Guide, Edition 3, this poster summarizes the stages of the cell cycle and DNA repair. It also highlights strategies for enhancing replicative stress in cancer cells to force mitotic catastrophe and cell death.
