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Revision as of 09:02, 31 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CASNo').← Previous edit Latest revision as of 08:48, 4 September 2024 edit undoLeophiee (talk | contribs)3 editsm Fixed a link in the Chembox.Tag: Visual edit 
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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 = <!-- blanked - oldvalue: 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}}


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==External links==
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