528124
Piperlongumine
A cell-permeable, orally bioavailable natural product isolated from the plant species, Piper longum L, which selectively induces cell death in cancer cells that express both wild-type and mutant p53.
Synonym(s):
Piperlongumine, Piplartine, (E)-1-(3-(3,4,5-Trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one
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100 μG
₩870,769
About This Item
Empirical Formula (Hill Notation):
C17H19NO5
CAS Number:
Molecular Weight:
317.34
MDL number:
UNSPSC Code:
12352100
NACRES:
NA.77
₩870,769
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Quality Level
Assay
≥97% (HPLC)
form
solid
manufacturer/tradename
Calbiochem®
storage condition
OK to freeze
protect from light
color
off-white
solubility
DMSO: soluble
shipped in
ambient
storage temp.
−20°C
SMILES string
O=C1N(C(/C=C/C2=CC(OC)=C(OC)C(OC)=C2)=O)CCC=C1
1 of 4
This Item | 617385 | 151882 | 756822 |
|---|---|---|---|
| technique(s) bio NMR: suitable | technique(s) HPLC: suitable | technique(s) NMR: suitable, bio NMR: suitable | technique(s) HPLC: suitable, bio NMR: suitable, protein expression: suitable |
| isotopic purity 70 atom % D | isotopic purity 99.8 atom % D | isotopic purity 99.9 atom % D | isotopic purity 99.8 atom % D |
| assay ≥69.5% (ATOM % D, qNMR) | assay - | assay - | assay - |
| Quality Level 200 | Quality Level 200 | Quality Level 200 | Quality Level 200 |
| form liquid | form liquid | form liquid | form liquid |
| storage temp. room temp | storage temp. - | storage temp. room temp | storage temp. room temp |
General description
A cell-permeable, orally bioavailable natural product isolated from the plant species, Piper longum L, which selectively induces cell death in cancer cells that express both wild-type and mutant p53, dose-dependently from 1–15 µM, but not in primary normal cells and non-transformed immortalized cells. It significantly enhances wild-type p53 and PUMA expression, and inhibits the expression of several pro-survival proteins, including BCL2, surviving, and XIAP, in various types of cancer cells, but not in normal cells. It elicits ROS and apoptosis in several human cancer cells (EJ, MDA-MB-231, U2OS and MDA-MB-435), possibly through interaction with oxidative stress responders such as GSTP1 and CBR1, and can be reversed by NAC (3 mM) in EJ cells. Additionally, it exhibits anti-tumour effects and inhibits the formation of blood vessels in xenograft-tumour mice without obvious toxicity, and inhibits tumor growth and their associated metastases in a MMTV-PyVT breast cancer transgenic mouse model ( 2.4 mg/kg, daily for two weeks, i.p.), which is more effective than paclitaxel.
Packaging
Packaged under inert gas
Warning
Toxicity: Regulatory Review (Z)
Reconstitution
Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
Other Notes
Raj, L., et al. 2011. Nature475, 231.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.
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