Piperlongumine

Piperlongumine
Names
	Preferred IUPAC name 1-[(2E)-3-(3,4,5-Trimethoxyphenyl)prop-2-enoyl]-5,6-dihydropyridin-2(1H)-one
	Other names Piplartine
Identifiers
CAS Number	20069-09-4 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL465843 ;
ChemSpider	553441 ;
ECHA InfoCard	100.243.690
PubChem CID	637858;
UNII	SGD66V4SVJ ;
CompTox Dashboard (EPA)	DTXSID801029762 ;
	InChI 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+ Key: VABYUUZNAVQNPG-BQYQJAHWSA-N ;
	SMILES O=C2\C=C/CCN2C(=O)\C=C\c1cc(OC)c(OC)c(OC)c1;
Properties
Chemical formula	C17H19NO5
Molar mass	317.341 g·mol−1
Solubility	DMSO, DMF, ethanol
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P280
Safety data sheet (SDS)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Piperlongumine (also called piplartine or piperlongumin) is an amide alkaloid constituent^[2] of the fruit of the long pepper (Piper longum), a pepper plant found in southern India and southeast Asia.^[3] When extracted, piperlongumine may cause skin, eye or respiratory tract irritation.^[2]

Traditional medicine and research

Long peppers have been used in Ayurveda and traditional Chinese medicine as a treatment.^[3]^[4]

Targtex, a biotechnology spin-off of the Portuguese Institute for Molecular Biology, developed a piperlongumine hydrogel that is to be applied after the removal of Glioblastoma tumours, with the goal of neutralizing remaining cancer cells. The hydrogel was effective in laboratory and animal studies and is scheduled for Phase I human clinical trials sometime in 2023.^[5]^[6]

References

^ ^a ^b "Safety Data Sheet Piperlongumine" (PDF). chemblink.com. October 1, 2018. Retrieved April 4, 2022.
^ ^a ^b "Piperlongumine". PubChem, US National Library of Medicine. 29 November 2020. Retrieved 5 December 2020.
^ ^a ^b Piska, Kamil; Gunia-Krzyżak, Agnieszka; Koczurkiewicz, Paulina; Wójcik-Pszczoła, Katarzyna; Pękala, Elżbieta (2018). "Piperlongumine (piplartine) as a lead compound for anticancer agents – Synthesis and properties of analogues: A mini-review". European Journal of Medicinal Chemistry. 156: 13–20. doi:10.1016/j.ejmech.2018.06.057. ISSN 0223-5234. PMID 30006159.
^ "Piperlongumine". US National Center for Advancing Translational Sciences. 2020. Retrieved 5 December 2020.
^ "Research & Technology | TargTex". Retrieved 2022-02-11.
^ Renascença (2022-02-11). "Português cria hidrogel de pimenta para combater cancro do cérebro - Renascença". Rádio Renascença (in European Portuguese). Retrieved 2022-02-11.

[MSDS-1] "Safety Data Sheet Piperlongumine" (PDF). chemblink.com. October 1, 2018. Retrieved April 4, 2022.

[pubchem-2] "Piperlongumine". PubChem, US National Library of Medicine. 29 November 2020. Retrieved 5 December 2020.

[piska-3] Piska, Kamil; Gunia-Krzyżak, Agnieszka; Koczurkiewicz, Paulina; Wójcik-Pszczoła, Katarzyna; Pękala, Elżbieta (2018). "Piperlongumine (piplartine) as a lead compound for anticancer agents – Synthesis and properties of analogues: A mini-review". European Journal of Medicinal Chemistry. 156: 13–20. doi:10.1016/j.ejmech.2018.06.057. ISSN 0223-5234. PMID 30006159.

[ncats-4] "Piperlongumine". US National Center for Advancing Translational Sciences. 2020. Retrieved 5 December 2020.

[5] "Research & Technology | TargTex". Retrieved 2022-02-11.

[6] Renascença (2022-02-11). "Português cria hidrogel de pimenta para combater cancro do cérebro - Renascença". Rádio Renascença (in European Portuguese). Retrieved 2022-02-11.

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