Piperlongumine: Difference between revisions

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	{{Chembox		{{Chembox
			\| Verifiedfields = changed
⚫	\| verifiedrevid = ~~443167274~~
			\| Watchedfields = changed
⚫	\| ImageFile = Piperlongumine.svg
		⚫	\| verifiedrevid = 458266837
	\| ImageSize = 200px
		⚫	\| ImageFile = Piperlongumine.svg
	\| ~~IUPACName~~ = 1--5,6-dihydropyridin-2(1''H'')-one		\| PIN = 1--5,6-dihydropyridin-2(1''H'')-one
	\| OtherNames = Piplartine		\| OtherNames = Piplartine
	\| Section1 = {{Chembox Identifiers		\| Section1 = {{Chembox Identifiers
	\| CASNo = 20069-09-4
	\| CASNo_Ref = {{cascite\|correct\|??}}		\| CASNo = 20069-09-4
			\| CASNo_Ref = {{cascite\|correct\|CAS}}
			\| UNII_Ref = {{fdacite\|correct\|FDA}}
⚫	\| ChEMBL = 465843
			\| UNII = SGD66V4SVJ
			\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}
		⚫	\| ChEMBL = 465843
	\| PubChem = 637858		\| PubChem = 637858
	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}		\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 553441		\| ChemSpiderID = 553441
	\| SMILES = O=C2\C=C/CCN2C(=O)\C=C\c1cc(OC)c(OC)c(OC)c1		\| SMILES = O=C2\C=C/CCN2C(=O)\C=C\c1cc(OC)c(OC)c(OC)c1
	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChI=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+		\| StdInChI=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+
	\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChIKey = VABYUUZNAVQNPG-BQYQJAHWSA-N		\| StdInChIKey = VABYUUZNAVQNPG-BQYQJAHWSA-N
	}}		}}
	\| Section2 = {{Chembox Properties		\| Section2 = {{Chembox Properties
	\| C=17\|H=19\|N=1\|O=5		\| C=17 \| H=19 \| N=1 \| O=5
	\| Appearance =		\| Appearance =
	\| Density =		\| Density =
	\| MeltingPt =		\| MeltingPt =
	\| BoilingPt =		\| BoilingPt =
	\| Solubility =		\| Solubility =
			\| SolubleOther = ], ], ]<ref name="MSDS">{{Cite web \|date=October 1, 2018 \|title=Safety Data Sheet Piperlongumine \|url=https://www.chemblink.com/MSDS/MSDSFiles/20069-09-4_Cayman.pdf \|access-date=April 4, 2022 \|website=chemblink.com}}</ref>
	}}		}}
	\| Section3 = {{Chembox Hazards		\| Section3 = {{Chembox Hazards
	\| MainHazards =		\| MainHazards =
	\| FlashPt =		\| FlashPt =
	\| ~~Autoignition~~ =		\| AutoignitionPt =
			\| ExternalSDS = <ref name="MSDS" />
			\| GHSPictograms = {{GHS07}}
			\| GHSSignalWord = Warning
			\| HPhrases = {{H-phrases\|315\|319\|335}}
			\| PPhrases = {{P-phrases\|261\|264\|280}}
	}}		}}
	}}		}}

			'''Piperlongumine''' (also called '''piplartine''' or '''piperlongumin''') is an ] ] constituent<ref name="pubchem">{{cite web \|title=Piperlongumine \|url=https://pubchem.ncbi.nlm.nih.gov/compound/Piperlongumine \|publisher=PubChem, US National Library of Medicine \|access-date=5 December 2020 \|date=29 November 2020}}</ref> of the fruit of the ] (''Piper longum''), a pepper plant found in ] and ].<ref name="piska">{{cite journal \| last1=Piska \| first1=Kamil \| last2=Gunia-Krzyżak \| first2=Agnieszka \| last3=Koczurkiewicz \| first3=Paulina \| last4=Wójcik-Pszczoła \| first4=Katarzyna \| last5=Pękala \| first5=Elżbieta \| title=Piperlongumine (piplartine) as a lead compound for anticancer agents – Synthesis and properties of analogues: A mini-review \| journal=European Journal of Medicinal Chemistry\| volume=156 \| year=2018 \| issn=0223-5234 \| doi=10.1016/j.ejmech.2018.06.057 \| pages=13–20\|pmid=30006159}}</ref> When ]ed, piperlongumine may cause skin, eye or ] irritation.<ref name=pubchem/>
	'''Piperlongumine''' (PL) is a ] constituent of the fruit of the ] (''Piper longum''),<ref name=Raj2011/> a pepper plant found in southern India and southeast Asia.

			==Traditional medicine and research==
	Piperlongumine may have anti-cancer properties. It selectively targets and kills cancer cells but leaving normal cells unharmed.<ref name=Raj2011>{{cite journal \| doi = 10.1038/nature10167 \| title = Selective killing of cancer cells by a small molecule targeting the stress response to ROS \| year = 2011 \| last1 = Raj \| first1 = Lakshmi \| last2 = Ide \| first2 = Takao \| last3 = Gurkar \| first3 = Aditi U. \| last4 = Foley \| first4 = Michael \| last5 = Schenone \| first5 = Monica \| last6 = Li \| first6 = Xiaoyu \| last7 = Tolliday \| first7 = Nicola J. \| last8 = Golub \| first8 = Todd R. \| last9 = Carr \| first9 = Steven A. \| journal = Nature \| volume = 475 \| issue = 7355 \| pages = 231–234 \| pmid = 21753854}}</ref> "In mice injected with human bladder, breast, lung, or melanoma cancer cells, PL inhibited tumor growth but showed no toxicity in normal mice. In a tougher test of mice that developed breast cancer spontaneously, PL blocked both tumor growth and metastasis."<ref>{{cite web\|url=http://www.sciencedaily.com/releases/2011/07/110713131421.htm \|title=Novel Compound Selectively Kills Cancer Cells by Blocking Their Response to Oxidative Stress \| publisher = ScienceDaily \| date=July 2011 }}</ref>
			Long peppers have been used in ] and ] as a treatment.<ref name=piska/><ref name="ncats">{{cite web \|title=Piperlongumine \|url=https://drugs.ncats.io/drug/SGD66V4SVJ \|publisher=US National Center for Advancing Translational Sciences \|access-date=5 December 2020 \|date=2020}}</ref>

			], a biotechnology spin-off of the Portuguese Institute for Molecular Biology, developed a piperlongumine hydrogel that is to be applied after the removal of ] 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.<ref>{{Cite web\|title=Research & Technology {{!}} TargTex\|url=https://targtex.com/research-technology/\|access-date=2022-02-11\|language=en-US}}</ref><ref>{{Cite web\|last=Renascença\|date=2022-02-11\|title=Português cria hidrogel de pimenta para combater cancro do cérebro - Renascença\|url=https://rr.sapo.pt/especial/pais/2022/02/11/portugues-cria-hidrogel-de-pimenta-para-combater-cancro-do-cerebro/272024/\|access-date=2022-02-11\|website=Rádio Renascença\|language=pt-pt}}</ref>
⚫	==References==

		⚫	== References ==
	{{reflist}}		{{reflist}}

		⚫	]
	==External links==
			]
	*
			]


⚫	]

Latest revision as of 08:48, 4 September 2024

Piperlongumine
Names

Preferred IUPAC name 1--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
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 , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

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

Traditional medicine and research

Long peppers have been used in Ayurveda and traditional Chinese medicine as a treatment.

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.

References

^ "Safety Data Sheet Piperlongumine" (PDF). chemblink.com. October 1, 2018. Retrieved April 4, 2022.
^ "Piperlongumine". PubChem, US National Library of Medicine. 29 November 2020. Retrieved 5 December 2020.
^ 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.

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