Synthetic analogue of the natural product piperlongumine as a potent inhibitor of breast cancer cell line migration

dc.contributor.authorValli, Marilia [UNESP]
dc.contributor.authorAltei, Wanessa
dc.contributor.authorDos Santos, Ricardo N.
dc.contributor.authorDe Lucca, Emilio C.
dc.contributor.authorDessoy, Marco A.
dc.contributor.authorPioli, Renan M. [UNESP]
dc.contributor.authorCotinguiba, Fernando
dc.contributor.authorCachet, Xavier
dc.contributor.authorMichel, Sylvie
dc.contributor.authorFurlan, Maysa [UNESP]
dc.contributor.authorDias, Luiz C.
dc.contributor.authorAndricopulo, Adriano D.
dc.contributor.authorBolzani, Vanderlan S. [UNESP]
dc.contributor.institutionUniversidade Estadual Paulista (Unesp)
dc.contributor.institutionUniversidade de São Paulo (USP)
dc.contributor.institutionUniversidade Estadual de Campinas (UNICAMP)
dc.contributor.institutionUniversidade Federal do Rio de Janeiro (UFRJ)
dc.contributor.institutionUniversit� Paris Descartes
dc.date.accessioned2018-12-11T17:31:13Z
dc.date.available2018-12-11T17:31:13Z
dc.date.issued2017-03-01
dc.description.abstractPiperlongumine is a natural amide alkaloid isolated from several species of Piper and is described in the literature as selectively cytotoxic to several cancer cell lines. Inhibiting cell migration has gained considerable interest as an approach for discovering antimetastatic agents because this process is fundamental to metastasis. Piperlongumine, selected from cell-based assay screening of NuBBE Database, inhibited the migration of MDA-MB-231 breast cancer cells with an EC50 of 3.0 � 1.0 μM by the Boyden chamber assay. A series of five analogous compounds based on the structure of piperlongumine were designed, synthesized and evaluated in cell migration and cytotoxicity assays. The analogue designed by molecular simplification ((E)-N-acryloyl-3-(3,4,5-trimethoxyphenyl)acrylamide) was the most active of the series, with an EC50 of 1.5 � 1 μM. Additionally, this compound was selectively cytotoxic, with a selectivity index (SI) of 4.4.en
dc.description.affiliationN�cleo de Bioensaios Bioss�ntese e Ecofisiologia de Produtos Naturais (NuBBE) Departamento de Qu�mica Org�nica Instituto de Qu�mica Universidade Estadual Paulista (UNESP)
dc.description.affiliationLaborat�rio de Qu�mica Medicinal e Computacional Centro de Pesquisa e Inova��o em Biodiversidade e F�rmacos Instituto de F�sica de S�o Carlos Universidade de S�o Paulo (USP)
dc.description.affiliationLaborat�rio de Qu�mica Org�nica Sint�tica Instituto de Qu�mica Universidade Estadual de Campinas (UNICAMP)
dc.description.affiliationInstituto de Pesquisas de Produtos Naturais (IPPN) Centro de Ci�ncias da Sa�de Universidade Federal do Rio de Janeiro (UFRJ)
dc.description.affiliationLaboratoire de Pharmacognosie UMR 8638 COMETE CNRS Facult� de Pharmacie de Paris Universit� Paris Descartes, Sorbonne Paris Cit�
dc.description.affiliationUnespN�cleo de Bioensaios Bioss�ntese e Ecofisiologia de Produtos Naturais (NuBBE) Departamento de Qu�mica Org�nica Instituto de Qu�mica Universidade Estadual Paulista (UNESP)
dc.description.sponsorshipCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)
dc.description.sponsorshipConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.description.sponsorshipFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.description.sponsorshipIdFAPESP: 2013/07600-3
dc.format.extent475-484
dc.identifierhttp://dx.doi.org/10.21577/0103-5053.20160303
dc.identifier.citationJournal of the Brazilian Chemical Society, v. 28, n. 3, p. 475-484, 2017.
dc.identifier.doi10.21577/0103-5053.20160303
dc.identifier.fileS0103-50532017000300475.pdf
dc.identifier.issn1678-4790
dc.identifier.issn0103-5053
dc.identifier.lattes1308042794786872
dc.identifier.scieloS0103-50532017000300475
dc.identifier.scopus2-s2.0-85009812446
dc.identifier.urihttp://hdl.handle.net/11449/178589
dc.language.isoeng
dc.relation.ispartofJournal of the Brazilian Chemical Society
dc.relation.ispartofsjr0,357
dc.relation.ispartofsjr0,357
dc.rights.accessRightsAcesso aberto
dc.sourceScopus
dc.subjectCell migration inhibition
dc.subjectCytotoxicity
dc.subjectPiperamide
dc.subjectPiperlongumine
dc.subjectPiplartine
dc.titleSynthetic analogue of the natural product piperlongumine as a potent inhibitor of breast cancer cell line migrationen
dc.typeArtigo
unesp.author.lattes1308042794786872

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