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.

• Sinônimo(s): Piperlongumine, Piplartine, (E)-1-(3-(3,4,5-Trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one
• Fórmula empírica (Notação de Hill): C₁₇H₁₉NO₅
• Número CAS: 20069-09-4
• Peso molecular: 317.34
• Número MDL: MFCD00075706
• Código UNSPSC: 12352100
• NACRES: NA.77

Propriedades

• Nível de qualidade: 100
• Ensaio: ≥97% (HPLC)
• Formulário: solid
• fabricante/nome comercial: Calbiochem^®
• condição de armazenamento: OK to freeze; protect from light
• cor: off-white
• solubilidade: DMSO: soluble
• Condições de expedição: ambient
• temperatura de armazenamento: −20°C
• cadeia de caracteres SMILES: O=C1N(C(/C=C/C2=CC(OC)=C(OC)C(OC)=C2)=O)CCC=C1
• 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+
• chave InChI: VABYUUZNAVQNPG-BQYQJAHWSA-N

Descrição

Descrição geral

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.

Embalagem

Packaged under inert gas

Advertência

Toxicity: Regulatory Review (Z)

Reconstituição

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Outras notas

Raj, L., et al. 2011. Nature475, 231.

Informações legais

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Informações de segurança

• Pictogramas: GHS07
• Palavra indicadora: Warning
• Frases de perigo: H302
• Declarações de precaução: P264 - P270 - P301 + P312 - P501
• Classificações de perigo: Acute Tox. 4 Oral
• Código de classe de armazenamento: 11 - Combustible Solids
• Classe de risco de água (WGK): WGK 3
• Ponto de fulgor (°F): Not applicable
• Ponto de fulgor (°C): Not applicable