Piperlongumine

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Cat.No. 4396 - Piperlongumine | C17H19NO5 | CAS No. 20069-09-4
Description: Induces apoptosis; increases p53 and ROS levels in cancer cells
Chemical Name: 5,6-Dihydro-1-[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propen-1-yl]-2(1H)-pyridinone
Purity: ≥97% (HPLC)
Datasheet
Citations (1)
Reviews
Literature
Pathways

Biological Activity

Induces cell death and increases the level of reactive oxygen species (ROS) in cancer cells with both wild-type and normal p53. Also inhibits the growth of spontaneous malignant breast tumors in mice. Displays little effect on normal cells. Rapidly depletes androgen receptor expression in human prostate cancer cells via a ROS-dependent, proteasome-mediated mechanism.

Technical Data

M. Wt 317.34
Formula C17H19NO5
Storage Store at -20°C
Purity ≥97% (HPLC)
CAS Number 20069-09-4
PubChem ID 637858
InChI Key VABYUUZNAVQNPG-BQYQJAHWSA-N
Smiles O=C1N(C(/C=C/C2=CC(OC)=C(OC)C(OC)=C2)=O)CCC=C1

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 31.73 100

Preparing Stock Solutions

The following data is based on the product molecular weight 317.34. 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 3.15 mL 15.76 mL 31.51 mL
5 mM 0.63 mL 3.15 mL 6.3 mL
10 mM 0.32 mL 1.58 mL 3.15 mL
50 mM 0.06 mL 0.32 mL 0.63 mL

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References

References are publications that support the biological activity of the product.

Raj et al (2011) Selective killing of cancer cells by a small molecule targeting the stress response to ROS. Nature 475 231 PMID: 21753854

Golovine et al (2012) Piperlongumine induces rapid depletion of the androgen receptor in human prostate cancer cells. Prostate [Epub ahead of print] PMID: 22592999


If you know of a relevant reference for Piperlongumine, please let us know.

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1 Citation for Piperlongumine

Citations are publications that use Tocris products. Selected citations for Piperlongumine include:

Farrand et al (2013) An improved quantitative approach for the assessment of mitochondrial fragmentation in chemoresistant ovarian cancer cells. PLoS One 8 e74008 PMID: 24040144


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Literature in this Area

Tocris offers the following scientific literature in this area to showcase our products. We invite you to request* or download your copy today!

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Cancer

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
Programmed Cell Death

Programmed Cell Death Poster

There are two currently recognized forms of programmed cell death: apoptosis and necroptosis. This poster summarizes the signaling pathways involved in apoptosis, necroptosis and cell survival following death receptor activation, and highlights the influence of the molecular switch, cFLIP, on cell fate.

Pathways for Piperlongumine

Apoptosis

Apoptosis Signaling Pathway

Apoptosis is a physiological process for cell death that is critical during aging and development. It may also be referred to as cell 'suicide'. Apoptosis can be triggered by events both inside and outside of the cell.