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Merck

SML0221

Sigma-Aldrich

Piperlongumine

≥97% (HPLC)

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C17H19NO5
Número de CAS:
Peso molecular:
317.34
Número MDL:
Código UNSPSC:
51111800
ID de la sustancia en PubChem:
NACRES:
NA.77

Nivel de calidad

Ensayo

≥97% (HPLC)

Formulario

powder

color

white to beige

solubilidad

DMSO: ≥5 mg/mL at warmed to 60 °C

temp. de almacenamiento

2-8°C

cadena SMILES

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+

Clave InChI

VABYUUZNAVQNPG-BQYQJAHWSA-N

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Descripción general

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.

Aplicación

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

Acciones bioquímicas o fisiológicas

Piperlongumine is an inhibitor or Glutathione S-transferase pi 1; Apoptosis Inducer in cancer, not normal cells
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.

Pictogramas

Exclamation mark

Palabra de señalización

Warning

Frases de peligro

Clasificaciones de peligro

Acute Tox. 4 Oral

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable


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Visite la Librería de documentos

ZNF32 protects against oxidative stress-induced apoptosis by modulating C1QBP transcription
Li K, et al.
Testing, 6(35), 38107-38107 (2015)
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)
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)
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
Piperlongumine suppresses growth and sensitizes pancreatic tumors to gemcitabine in a xenograft mouse model by modulating the NF-kappa B pathway
Wang Y, et al.
Cancer Prevention Research (Philadelphia, Pa.), 9(3), 234-244 (2016)

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