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.

• 동의어(들): Piperlongumine, Piplartine, (E)-1-(3-(3,4,5-Trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one
• 실험식(Hill 표기법): C₁₇H₁₉NO₅
• CAS Number: 20069-09-4
• Molecular Weight: 317.34
• MDL number: MFCD00075706
• UNSPSC 코드: 12352100
• NACRES: NA.77

속성

• Quality Level: 100
• 분석: ≥97% (HPLC)
• 양식: solid
• 제조업체/상표: Calbiochem^®
• 저장 조건: OK to freeze; protect from light
• 색상: off-white
• solubility: DMSO: soluble
• 배송 상태: ambient
• 저장 온도: −20°C
• SMILES string: 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+
• InChI key: VABYUUZNAVQNPG-BQYQJAHWSA-N

설명

일반 설명

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.

포장

Packaged under inert gas

경고

Toxicity: Regulatory Review (Z)

재구성

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

기타 정보

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

법적 정보

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

안전성 정보

• 픽토그램: GHS07
• 신호어: Warning
• 유해 및 위험 성명서: H302
• 예방조치 성명서: P264 - P270 - P301 + P312 - P501
• Hazard Classifications: Acute Tox. 4 Oral
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point (°F): Not applicable
• Flash Point (°C): Not applicable