PIPERLONGUMINE

Alkaloids

NP0012

20069-09-4

PIPERLONGUMINE

Piperlongumine, also known as Piplartine , is a biologically active alkaloid/amide from peppers, as from long pepper (Piper longum L. - Piperaceae). Long pepper is one of the most widely used in Ayurvedic medicine, which is used to treat many diseases, including tumors. The reported pharmacological activities of piplartine include cytotoxic, genotoxic, antitumor, antiangiogenic, antimetastatic, antiplatelet aggregation, antinociceptive, anxiolytic, antidepressant, anti-atherosclerotic, antidiabetic, antibacterial, antifungal, leishmanicidal, trypanocidal, and schistosomicidal activities. Among the multiple pharmacological effects of piplartine, its anticancer property is the most promising. Therefore, the preclinical anticancer potential of piplartine has been extensively investigated, which recently resulted in one patent. This compound is selectively cytotoxic against cancer cells by induction of oxidative stress, induces genotoxicity, as an alternative strategy to killing tumor cells, has excellent oral bioavailability in mice, inhibits tumor growth in mice, and presents only weak systemic toxicity.

Piplartine; 5,6-Dihydro-1-[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propen-1-yl]-2(1H)-pyridinone; (E)-5,6-Dihydro-1-[1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]-2(1H)-pyridinone; Piplartin; (E)-1-(3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one; NSC-794671

1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one

317.34

C17H19NO5

COC1=CC(=CC(=C1OC)OC)C=CC(=O)N2CCC=CC2=O

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

475.6±45.0°C (Predicted)

122-124°C

241.4°C

≥98%

1.223±0.06 g/cm3 (Predicted)

Soluble in Chloroform (Slightly), Methanol (Slightly)

Off-white to Yellow Solid

Store at -20°C

Pale Yellow to Yellow

Solid

MFCD00075706

NA.77

-1.88±0.20(Predicted)

100

UU7785850

Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.

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.

3