WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 406245
CAS#: 20069-09-4
Description: Piperlongumine , also known as Piplartine , is a biologically active alkaloid/amide from peppers, as from long pepper (Piper longum L. - Piperaceae). Long pepper is one of the most widely used in Ayurvedic medicine, which is used to treat many diseases, including tumors. The reported pharmacological activities of piplartine include cytotoxic, genotoxic, antitumor, antiangiogenic, antimetastatic, antiplatelet aggregation, antinociceptive, anxiolytic, antidepressant, anti-atherosclerotic, antidiabetic, antibacterial, antifungal, leishmanicidal, trypanocidal, and schistosomicidal activities. Among the multiple pharmacological effects of piplartine, its anticancer property is the most promising.
MedKoo Cat#: 406245
Name: Piperlongumine
CAS#: 20069-09-4
Chemical Formula: C17H19NO5
Exact Mass: 317.12632
Molecular Weight: 317.34
Elemental Analysis: C, 64.34; H, 6.03; N, 4.41; O, 25.21
Synonym: Piperlongumine; Piplartine.
IUPAC/Chemical Name: (E)-1-(3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one
InChi Key: VABYUUZNAVQNPG-BQYQJAHWSA-N
InChi Code: 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+
SMILES Code: O=C1C=CCCN1C(/C=C/C2=CC(OC)=C(OC)C(OC)=C2)=O
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >5 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 317.34 Batch specific molecular weights may vary from batch to batch due to the degree 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 | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Jarvius M, Fryknäs M, D'Arcy P, Sun C, Rickardson L, Gullbo J, Haglund C, Nygren P, Linder S, Larsson R. Piperlongumine induces inhibition of the ubiquitin-proteasome system in cancer cells. Biochem Biophys Res Commun. 2013 Feb 8;431(2):117-23. doi: 10.1016/j.bbrc.2013.01.017. Epub 2013 Jan 11. PubMed PMID: 23318177.
2: Bezerra DP, Pessoa C, de Moraes MO, Saker-Neto N, Silveira ER, Costa-Lotufo LV. Overview of the therapeutic potential of piplartine (piperlongumine). Eur J Pharm Sci. 2012 Dec 11;48(3):453-463. doi: 10.1016/j.ejps.2012.12.003. [Epub ahead of print] PubMed PMID: 23238172.
3: Han SS, Son DJ, Yun H, Kamberos NL, Janz S. Piperlongumine inhibits proliferation and survival of Burkitt lymphoma in vitro. Leuk Res. 2013 Feb;37(2):146-54. doi: 10.1016/j.leukres.2012.11.009. Epub 2012 Dec 10. PubMed PMID: 23237561; PubMed Central PMCID: PMC3551475.
4: Son DJ, Kim SY, Han SS, Kim CW, Kumar S, Park BS, Lee SE, Yun YP, Jo H, Park YH. Piperlongumine inhibits atherosclerotic plaque formation and vascular smooth muscle cell proliferation by suppressing PDGF receptor signaling. Biochem Biophys Res Commun. 2012 Oct 19;427(2):349-54. doi: 10.1016/j.bbrc.2012.09.061. Epub 2012 Sep 17. PubMed PMID: 22995306; PubMed Central PMCID: PMC3495231.
5: Adams DJ, Dai M, Pellegrino G, Wagner BK, Stern AM, Shamji AF, Schreiber SL. Synthesis, cellular evaluation, and mechanism of action of piperlongumine analogs. Proc Natl Acad Sci U S A. 2012 Sep 18;109(38):15115-20. Epub 2012 Sep 4. PubMed PMID: 22949699; PubMed Central PMCID: PMC3458345.
6: Zi J, Gladstone SG, Zhan J. Specific 5-hydroxylation of piperlongumine by Beauveria bassiana ATCC 7159. Biosci Biotechnol Biochem. 2012;76(8):1565-7. Epub 2012 Aug 7. PubMed PMID: 22878194.
7: Golovine KV, Makhov PB, Teper E, Kutikov A, Canter D, Uzzo RG, Kolenko VM. Piperlongumine induces rapid depletion of the androgen receptor in human prostate cancer cells. Prostate. 2013 Jan;73(1):23-30. doi: 10.1002/pros.22535. Epub 2012 May 16. PubMed PMID: 22592999; PubMed Central PMCID: PMC3491117.
8: Park BS, Son DJ, Choi WS, Takeoka GR, Han SO, Kim TW, Lee SE. Antiplatelet activities of newly synthesized derivatives of piperlongumine. Phytother Res. 2008 Sep;22(9):1195-9. doi: 10.1002/ptr.2432. PubMed PMID: 18697182.
9: Iwashita M, Oka N, Ohkubo S, Saito M, Nakahata N. Piperlongumine, a constituent of Piper longum L., inhibits rabbit platelet aggregation as a thromboxane A(2) receptor antagonist. Eur J Pharmacol. 2007 Sep 10;570(1-3):38-42. Epub 2007 Jun 15. PubMed PMID: 17618620.
10: Chatterjee A, Dutta CP. Alkaloids of Piper longum Linn. I. Structure and synthesis of piperlongumine and piperlonguminine. Tetrahedron. 1967 Apr;23(4):1769-81. PubMed PMID: 6047519.
