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.

• Sinonimo/i: Piperlongumine, Piplartine, (E)-1-(3-(3,4,5-Trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one
• Formula empirica (notazione di Hill): C₁₇H₁₉NO₅
• Numero CAS: 20069-09-4
• Peso molecolare: 317.34
• Numero MDL: MFCD00075706
• Codice UNSPSC: 12352100
• NACRES: NA.77

Proprietà

• Livello qualitativo: 100
• Saggio: ≥97% (HPLC)
• Forma fisica: solid
• Produttore/marchio commerciale: Calbiochem^®
• Condizioni di stoccaggio: OK to freeze; protect from light
• Colore: off-white
• Solubilità: DMSO: soluble
• Condizioni di spedizione: ambient
• Temperatura di conservazione: −20°C
• Stringa SMILE: 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+; VABYUUZNAVQNPG-BQYQJAHWSA-N

Descrizione

Descrizione generale

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.

Confezionamento

Packaged under inert gas

Attenzione

Toxicity: Regulatory Review (Z)

Ricostituzione

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

Altre note

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

Note legali

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

Informazioni sulla sicurezza

• Pittogrammi: GHS07
• Avvertenze: Warning
• Indicazioni di pericolo: H302
• Consigli di prudenza: P264 - P270 - P301 + P312 - P501
• Classi di pericolo: Acute Tox. 4 Oral
• Codice della classe di stoccaggio: 11 - Combustible Solids
• Classe di pericolosità dell'acqua (WGK): WGK 3
• Punto d’infiammabilità (°F): Not applicable
• Punto d’infiammabilità (°C): Not applicable