Piplartine

Names

[ CAS No. ]:
20069-09-4

[ Name ]:
Piplartine

[Synonym ]:
Piperlongumine
1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one
2(1H)-Pyridinone, 5,6-dihydro-1-[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propen-1-yl]-
(E)-Piplartine
1-[(2E)-3-(3,4,5-Trimethoxyphenyl)-2-propenoyl]-5,6-dihydro-2(1H)-pyridinone
piplartine
1-[3-(3,4,5-Trimethoxy-phenyl)-acryloyl]-5,6-dihydro-1H-pyridin-2-one
2(1H)-Pyridinone, 5,6-dihydro-1-(1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)-, (E)-
1-[(2E)-3-(3,4,5-Trimethoxyphenyl)prop-2-enoyl]-5,6-dihydropyridin-2(1H)-one

Biological Activity

[Description]:

Piperlongumine is a natural alkaloid isolated from Piper longum Linn[1], possesses ant-inflammatory, antibacterial, antiangiogenic, antioxidant, antitumor, and antidiabetic activities[2]. Piperlongumine induces ROS, and induces apoptosis in cancer cell lines[1]. Piperlongumine shows anti-cardiac fibrosis activity, suppresses myofibroblast transformation via suppression of the ERK1/2 signaling pathway[2].

[Related Catalog]:

Signaling Pathways >> MAPK/ERK Pathway >> ERK

Signaling Pathways >> Stem Cell/Wnt >> ERK

Natural Products >> Alkaloid

Research Areas >> Cancer

Research Areas >> Cardiovascular Disease

Research Areas >> Infection

[Target]

ERK1

ERK2

[In Vitro]

Piplartine (5, 10, and 15 μM) significantly decreases cell proliferation of 786-O, SKBR3, Panc1, A549, and L3.6pL cancer cells after treatment for 24 and 48 hours, induces apoptosis and ROS in these cell lines at 5 and 10 μM after 3 or 9 h of treatment[1]. Piplartine (5 or 10 μM) induces cleaved PARP and downregulates Sp1, Sp3, Sp4, and Sp-regulated genes[1]. Piplartine (20 μM) decreases the viability of cardiac fibroblasts (CFs). Piplartine (0-10 μM) suppresses myofibroblast transformation via suppression of the ERK1/2 signaling pathway[2].

[In Vivo]

Piperlongumine (30 mg/kg/day, i.p. for 3 weeks) exhibits potent anti-tumor effect in athymic nude mice bearing L3.6pL cells without body weight loss[1].

[References]

[1]. Karki K, et al. Piperlongumine Induces Reactive Oxygen Species (ROS)-Dependent Downregulation of Specificity Protein Transcription Factors.

[2]. Wu X, e,t al. Piperlongumine inhibits angiotensin II-induced extracellular matrix expression in cardiac fibroblasts. J Cell Biochem. 2018 Dec;119(12):10358-10364

[Related Small Molecules]

SCH772984 | Ravoxertinib | Honokiol | Sodium tauroursodeoxycholate | LY3214996 | Ulixertinib (BVD-523) | TIC10 | Astragaloside IV | XMD8-92 | LM22B 10 | VX-11e | FR 180204 | Mogrol | Pluripotin | AX 15836

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
475.6±45.0 °C at 760 mmHg

[ Melting Point ]:
124ºC

[ Molecular Formula ]:
C₁₇H₁₉NO₅

[ Molecular Weight ]:
317.336

[ Flash Point ]:
241.4±28.7 °C

[ Exact Mass ]:
317.126312

[ PSA ]:
65.07000

[ LogP ]:
2.34

[ Appearance of Characters ]:
white to beige

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.581

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
DMSO: ≥5mg/mL at warmed to 60°C

MSDS

Click to get detail MSDS

Safety Information

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
UU7785850

[ HS Code ]:
2933399090

Synthetic Route

Click to get detail synthetic route

Customs

[ HS Code ]: 2933399090

[ Summary ]:
2933399090. other compounds containing an unfused pyridine ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Serotonergic signalling suppresses ataxin 3 aggregation and neurotoxicity in animal models of Machado-Joseph disease.

Brain 138 , 3221-37, (2015)

Polyglutamine diseases are a class of dominantly inherited neurodegenerative disorders for which there is no effective treatment. Here we provide evidence that activation of serotonergic signalling is...

Piperlongumine induces apoptotic and autophagic death of the primary myeloid leukemia cells from patients via activation of ROS-p38/JNK pathways.

Acta Pharmacol. Sin. 36(3) , 362-74, (2015)

To investigate the effects of piperlongumine (PL), an anticancer alkaloid from long pepper plants, on the primary myeloid leukemia cells from patients and the mechanisms of action.Human BM samples wer...

Piperlongumine for Enhancing Oral Bioavailability and Cytotoxicity of Docetaxel in Triple-Negative Breast Cancer.

J. Pharm. Sci. 104 , 4417-26, (2016)

Very low oral bioavailability due to extensive pre-systemic metabolism and P-gp efflux has constrained the oral metronomic chemotherapy of docetaxel (DTX). There is tremendous need of compounds facili...