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Chemical Structure| 20069-09-4 Chemical Structure| 20069-09-4

Structure of Piperlongumine
CAS No.: 20069-09-4

Chemical Structure| 20069-09-4

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Piperlongumine, a natural alkaloid from Piper longum L., increases the level of reactive oxygen species (ROS) and selectively kills cancer cells. It is a direct TrxR1 inhibitor with suppressive activity against gastric cancer and an inhibitor of CRM1 and is also an inhibitor of PI3K/Akt/mTOR in human breast cancer cells.

Synonyms: Piplartine; PPLGM

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Product Details of Piperlongumine

CAS No. :20069-09-4
Formula : C17H19NO5
M.W : 317.34
SMILES Code : O=C1C=CCCN1C(/C=C/C2=CC(OC)=C(C(OC)=C2)OC)=O
Synonyms :
Piplartine; PPLGM
MDL No. :MFCD00075706
InChI Key :VABYUUZNAVQNPG-BQYQJAHWSA-N
Pubchem ID :637858

Safety of Piperlongumine

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H320-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Isoform Comparison

Biological Activity

Target
  • CRM1

In Vitro:

Cell Line
Concentration Treated Time Description References
Primary neurons 0.1 µM 24 hours PLG reduced cell injury and cell death induced by rotenone Autophagy. 2018;14(5):845-861.
293T cells 0.1 µM 8 hours Induced CDK9 degradation Cell Chem Biol. 2023 Feb 16;30(2):203-213.e17.
K562 cells 0.1 µM 8 hours Induced CDK9 degradation Cell Chem Biol. 2023 Feb 16;30(2):203-213.e17.
MOLT4 cells 0.1 µM 16 hours Induced CDK9 degradation Cell Chem Biol. 2023 Feb 16;30(2):203-213.e17.
High-grade glioma sphere cultures 0-10 mM 1-3 days Piperlongumine treatment increased ROS levels and preferentially killed HGG cells with little effect in normal brain cells. Neuro Oncol. 2014 Oct;16(10):1354-64.
Neural stem cell (NSC) sphere cultures 0-10 mM 1-3 days Piperlongumine treatment had little effect on the growth of neural stem cells. Neuro Oncol. 2014 Oct;16(10):1354-64.
Astrocytes 0-10 mM 1-3 days Piperlongumine treatment at the highest dose of 10 mM suppressed the growth of astrocyte cultures. Neuro Oncol. 2014 Oct;16(10):1354-64.
SK-N-SH cells 0.1 - 2.5 µM 24 hours PLG partially reversed the decrease in cell viability and increase in cytotoxicity induced by rotenone Autophagy. 2018;14(5):845-861.
Primary neurons 0.1 µM 24 hours PLG reduced cell injury and cell death rate induced by rotenone Autophagy. 2018;14(5):845-861.
SK-N-SH cells 0.1 - 2.5 µM 24 hours PLG partly abrogated the reduction in cell viability and enhancement in cytotoxicity induced by rotenone Autophagy. 2018;14(5):845-861.
A549 cells 0 to 50 µM 24 hours To evaluate the cytotoxicity of Piperlongumine on A549 cells, the results showed that Piperlongumine has cytotoxicity on A549 cells in the range of 0 to 50 µM. Antioxidants (Basel). 2022 Apr 4;11(4):710.
HCT116 cells 0 to 50 µM 24 hours To evaluate the cytotoxicity of Piperlongumine on HCT116 cells, the results showed that Piperlongumine has cytotoxicity on HCT116 cells in the range of 0 to 50 µM. Antioxidants (Basel). 2022 Apr 4;11(4):710.
HepG2 cells 0 to 50 µM 24 hours To evaluate the cytotoxicity of Piperlongumine on HepG2 cells, the results showed that Piperlongumine has cytotoxicity on HepG2 cells in the range of 0 to 50 µM. Antioxidants (Basel). 2022 Apr 4;11(4):710.
MCF-7 cells 0 to 50 µM 24 hours To evaluate the cytotoxicity of Piperlongumine on MCF-7 cells, the results showed that Piperlongumine has cytotoxicity on MCF-7 cells in the range of 0 to 50 µM. Antioxidants (Basel). 2022 Apr 4;11(4):710.

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
C57BL mice Rotenone-induced Parkinson's disease model Oral 2 and 4 mg/kg Once daily for 4 weeks PLG attenuated motor deficits in mice and prevented the loss of dopaminergic neurons induced by rotenone Autophagy. 2018;14(5):845-861.
C57BL/6J mice Chemotherapy-induced cognitive impairment model Intraperitoneal injection 2 mg/kg Weekly for 12 weeks To investigate the neuroprotective role of Piperlongumine in chemotherapy-induced cognitive impairment. Results showed that TAC/PL co-treated mice did not exhibit measurable social memory deficits during social memory testing, indicating that Piperlongumine protects against TAC-induced social memory impairment. Int J Mol Sci. 2022 Feb 11;23(4):2008

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

3.15mL

0.63mL

0.32mL

15.76mL

3.15mL

1.58mL

31.51mL

6.30mL

3.15mL

 

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