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Piperlongumine
- Piplartine
- Soluble in DMSO
- MF: C17H19NO5
- MW: 317.34
Description
Natural alkaloid with potent cytotoxic activity which has been related to an increased reactive oxygen species (ROS) generation in cancer cells (through direct GSTP1 interaction), down-regulation of nuclear factor-kB (NF-kB) activation and induction of rapid depletion of the androgen receptor (AR) in prostate cancer cells. Moreover, Piperlongumine (or Piplartine) was found to induce apoptosis and autophagy through modulation of the PI3K/Akt/mTOR pathway in human lung cancer cells, and potently inhibited ligand-stimulated STAT3 nuclear translocation.
More Information
| Parent CAS No. | 20069-09-4 |
|---|---|
| Chemical Name | (E)-1-(3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one |
| SMILES | C1(=O)N(C(=O)/C=C/C2=CC(OC)=C(OC)C(OC)=C2)CCC=C1 |
| MFCD | MFCD00075706 |
| InChi | InChI=1S/C17H19NO5/c1-21-13-10-12(11-14(22-2)17(13)23-3)7-8-16(20)18-9-5-4-6-15(18)19/h4,6-8,10-11H,5,9H2,1-3H3/b8-7+ |
| InChiKey | VABYUUZNAVQNPG-BQYQJAHWSA-N |
| CID | 637858 |
| Short Description | Natural alkaloid/GSTP1 inhibitor |
References
- R.C. Barcelos et al. Design and synthesis of N-acylated aza-goniothalamin derivatives and evaluation of their in vitro and in vivo antitumor activity. ChemMedChem. 2014 Dec;9(12):2725-43.
- F. Wang et al. Piperlongumine induces apoptosis and autophagy in human lung cancer cells through inhibition of PI3K/Akt/mTOR pathway. Int J Immunopathol Pharmacol. 2015 Sep;28(3):362-73.
- S. Ginzburg et al. Piperlongumine inhibits NF-κB activity and attenuates aggressive growth characteristics of prostate cancer cells. Prostate. 2014 Feb;74(2):177-86.
- U. Bharadwaj et al. Drug-repositioning screening identified piperlongumine as a direct STAT3 inhibitor with potent activity against breast cancer. Oncogene. 2015 Mar 12;34(11):1341-53.
- D.J. Adams et al. Synthesis, cellular evaluation, and mechanism of action of piperlongumine analogs. Proc Natl Acad Sci U S A. 2012 Sep 18;109(38):15115-20.
- M. Jarvius et al. Piperlongumine induces inhibition of the ubiquitin-proteasome system in cancer cells. Biochem Biophys Res Commun. 2013 Feb 8;431(2):117-23.
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