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Piperlongumine

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Revision as of 09:13, 31 October 2011 by CheMoBot (talk | contribs) (Updating {{chembox}} (changes to verified fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WikiProject_Chemicals|errors...)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff)
Piperlongumine
Names
IUPAC name 1--5,6-dihydropyridin-2(1H)-one
Other names Piplartine
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.243.690 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
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+Key: VABYUUZNAVQNPG-BQYQJAHWSA-N
SMILES
  • O=C2\C=C/CCN2C(=O)\C=C\c1cc(OC)c(OC)c(OC)c1
Properties
Chemical formula C17H19NO5
Molar mass 317.341 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Piperlongumine (PL) is a natural product constituent of the fruit of the Long pepper (Piper longum), a pepper plant found in southern India and southeast Asia.

Piperlongumine may have anti-cancer properties. It selectively targets and kills cancer cells but leaving normal cells unharmed. "In mice injected with human bladder, breast, lung, or melanoma cancer cells, PL inhibited tumor growth but showed no toxicity in normal mice. In a tougher test of mice that developed breast cancer spontaneously, PL blocked both tumor growth and metastasis."

References

  1. ^ Raj, Lakshmi; Ide, Takao; Gurkar, Aditi U.; Foley, Michael; Schenone, Monica; Li, Xiaoyu; Tolliday, Nicola J.; Golub, Todd R.; Carr, Steven A. (2011). "Selective killing of cancer cells by a small molecule targeting the stress response to ROS". Nature. 475 (7355): 231–234. doi:10.1038/nature10167. PMID 21753854.
  2. "Novel Compound Selectively Kills Cancer Cells by Blocking Their Response to Oxidative Stress". ScienceDaily. July 2011.

External links

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