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SML0221

Sigma-Aldrich

Piperlongumine

≥97% (HPLC)

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Synonym(s):
5,6-Dihydro-1-(1-oxo-3-[3,4,5-trimethoxyphenyl]-trans-2-propenyl)-2[1H]-pyridinone, 5,6-Dihydro-1-[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propen-1-yl]-2(1H)-Pyridinone, Piplartin, Piplartine
Empirical Formula (Hill Notation):
C17H19NO5
CAS Number:
Molecular Weight:
317.34
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥97% (HPLC)

form

powder

color

white to beige

solubility

DMSO: ≥5 mg/mL at warmed to 60 °C

storage temp.

2-8°C

SMILES string

COc1cc(\C=C\C(=O)N2CCC=CC2=O)cc(OC)c1OC

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+

InChI key

VABYUUZNAVQNPG-BQYQJAHWSA-N

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This Item
528124SML1498SML2798
Piperlongumine ≥97% (HPLC)

SML0221

Piperlongumine

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.

528124

Piperlongumine

Cinepazide maleate ≥98% (HPLC)

SML1498

Cinepazide maleate

Sigma-Aldrich

SML2798

CH625

form

powder

form

solid

form

powder

form

powder

Quality Level

100

Quality Level

100

Quality Level

-

Quality Level

100

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

solubility

DMSO: ≥5 mg/mL at warmed to 60 °C

solubility

DMSO: soluble

solubility

H2O: 20 mg/mL, clear

solubility

DMSO: 2 mg/mL, clear

color

white to beige

color

off-white

color

white to beige

color

white to beige

General description

Piperlongumine is an alkaloid, which is extracted from Piper longum Linn. It exhibits anti-atherosclerotic, anxiolytic, antidiabetic, antidepressant, antibacterial, anti-platelet, aggregation, anxiolytic and anti-inflammatory properties. Piperlongumine prevents the production of tumor necrosis factor-α and interleukin-6. It blocks the activation of nuclear factor-κB (NF-κB) against proinflammatory responses. Piperlongumine inhibits plaque formation and inhibits vascular smooth muscle cell migration. It is used to treat cough, respiratory infections and stomach-ache.

Application

Piperlongumine has been used to study the regulation of protein regulator of cytokinesis 1 (PRC1) expression. It has also been used to investigate its anti-tumor effects on human melanoma cells in vitro.
Piperlongumine has been used:
  • as a pro-oxidant drug to treat HepG2 cells expressing zinc finger protein (ZNF)32
  • to test its anti-neuroinflammatory effects in BV2 microglial cells
  • to test its inhibitory effect on human gastric cancer cell lines

Biochem/physiol Actions

Piperlongumine selectively kills cancer cells regardless of p53 status without harming normal cells. It binds to and inihbits proteins known to regulate oxidative stress, in particular, Glutathione S-transferase pi 1 (GSTP1). It increases the level of reactive oxygen species (ROS) and apoptotic cell death in cancer cells with little effect on either rapidly or slowly dividing primary normal cells. Piperlongumine showed significant antitumour effects in a variety of mouse tumour models and inhibited growth of spontaneously formed malignant breast tumours and their associated metastases.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Alhassan Aodah et al.
PloS one, 11(3), e0151707-e0151707 (2016-03-18)
Piperlongumine is a natural alkaloid extracted from piper plants which has been used traditionally for the treatment of certain diseases. This compound shows interesting in vitro pharmacological activity such as selective anticancer activity and higher cytotoxicity than methotrexate, cyclophosphamide and
ZNF32 protects against oxidative stress-induced apoptosis by modulating C1QBP transcription
Li K, et al.
Testing, 6(35), 38107-38107 (2015)
Piperlongumine inhibits neuroinflammation via regulating NF-kappaB signaling pathways in lipopolysaccharide-stimulated BV2 microglia cells
Kim N, et al.
Journal of Pharmacological Sciences, 137(2), 195-201 (2018)
Piperlongumine Induces Apoptosis in Human Melanoma Cells Via Reactive Oxygen Species Mediated Mitochondria Disruption
Song X, et al.
Nutrition and Cancer, 70(3), 502-511 (2018)
Wenxiang Shi et al.
Frontiers in cardiovascular medicine, 7, 625215-625215 (2021-03-02)
Vascular calcification frequently occurs in the process of chronic kidney disease, atherosclerosis and aging, resulting in an increased prevalence of cardiovascular events. Piperlongumine (PLG) is a natural product isolated from Piper longum L. Here, we aimed to explore the effect

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