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Structure–Activity Relationship of Piplartine and Synthetic Analogues against Schistosoma mansoni and Cytotoxicity to Mammalian Cells

2018-06Journal article Open access
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dc.contributor.authorCampelo, Yuri
dc.contributor.authorOmbredane, Alicia
dc.contributor.authorVasconcelos, Andreanne
dc.contributor.authorAlbuquerque, Lucas
dc.contributor.authorMoreira, Daniel
dc.contributor.authorPlácido, Alexandra
dc.contributor.authorRocha, Jefferson
dc.contributor.authorFokoue, Harold Hilarion
dc.contributor.authorYamaguchi, Lydia
dc.contributor.authorMafud, Ana
dc.contributor.authorMascarenhas, Yvonne
dc.contributor.authorDelerue-Matos, Cristina
dc.contributor.authorBorges, Tatiana
dc.contributor.authorJoanitti, Graziella
dc.contributor.authorArcanjo, Daniel
dc.contributor.authorKato, Massuo
dc.contributor.authorKuckelhaus, Selma
dc.contributor.authorSilva, Marcos
dc.contributor.authorMoraes, Josué
dc.contributor.authorLeite, José
dc.date.accessioned2019-09-13T09:45:41Z
dc.date.available2019-09-13T09:45:41Z
dc.date.issued2018-06
dc.description.abstractSchistosomiasis, caused by helminth flatworms of the genus Schistosoma, is an infectious disease mainly associated with poverty that affects millions of people worldwide. Since treatment for this disease relies only on the use of praziquantel, there is an urgent need to identify new antischistosomal drugs. Piplartine is an amide alkaloid found in several Piper species (Piperaceae) that exhibits antischistosomal properties. The aim of this study was to evaluate the structure–function relationship between piplartine and its five synthetic analogues (19A, 1G, 1M, 14B and 6B) against Schistosoma mansoni adult worms, as well as its cytotoxicity to mammalian cells using murine fibroblast (NIH-3T3) and BALB/cN macrophage (J774A.1) cell lines. In addition, density functional theory calculations and in silico analysis were used to predict physicochemical and toxicity parameters. Bioassays revealed that piplartine is active against S. mansoni at low concentrations (5⁻10 µM), but its analogues did not. In contrast, based on 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) and flow cytometry assays, piplartine exhibited toxicity in mammalian cells at 785 µM, while its analogues 19A and 6B did not reduce cell viability at the same concentrations. This study demonstrated that piplartine analogues showed less activity against S. mansoni but presented lower toxicity than piplartine.pt_PT
dc.description.sponsorshipThis work was partially supported by grants from the Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP grant number 2016/22488-3), the authors are grateful to CAPES/FAPEPI for the scholarship granted. ACM is grateful to FAPESP (2014/02282-6). YPM is grateful to CNPq (Grant 302674/2010-1). Financial Support: FCT (Fundação para Ciência e Tecnologia) by grant no. UID/MULTI/04378/2013 POCI/01/0145/FEDER/007728, Fapesp (2014/50316-7). The work at UCIBIO/Requimte was supported by the Fundação para a Ciência e a Tecnologia (FCT) with financial support from FCT/MEC through national funds and co-financed by FEDER, under the Partnership Agreement PT2020. Alexandra Plácido is grateful to FCT by her grant SFRH/BD/97995/2013, financed by POPH–QREN–Tipologia 4.1–Formação Avançada, subsidized by Fundo Social Europeu and Ministério da Ciência, Tecnologia e Ensino Superior.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.doi10.3390/ijms19061802
dc.identifier.urihttp://hdl.handle.net/10400.22/14597
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherMDPIpt_PT
dc.relation.publisherversionhttps://www.mdpi.com/1422-0067/19/6/1802pt_PT
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/pt_PT
dc.subject3T3 Cellspt_PT
dc.subjectAnimalspt_PT
dc.subjectAnthelminticspt_PT
dc.subjectCricetinaept_PT
dc.subjectFibroblastspt_PT
dc.subjectMacrophagespt_PT
dc.subjectMicept_PT
dc.subjectMice, Inbred BALB Cpt_PT
dc.subjectPiperpt_PT
dc.subjectPiperidonespt_PT
dc.subjectPlant Extractspt_PT
dc.subjectQuantitative Structure-Activity Relationshippt_PT
dc.subjectSchistosoma mansonipt_PT
dc.subjectSnailspt_PT
dc.titleStructure–Activity Relationship of Piplartine and Synthetic Analogues against Schistosoma mansoni and Cytotoxicity to Mammalian Cellspt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/5876/UID%2FMulti%2F04378%2F2013/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/SFRH/SFRH%2FBD%2F97995%2F2013/PT
oaire.citation.issue6pt_PT
oaire.citation.startPage1802pt_PT
oaire.citation.titleInternational Journal of Molecular Sciencespt_PT
oaire.citation.volume19pt_PT
oaire.fundingStream5876
oaire.fundingStreamSFRH
person.familyNamePlácido
person.familyNameDelerue-Matos
person.givenNameAlexandra
person.givenNameCristina
person.identifier1621053
person.identifier.ciencia-id1B1A-461B-E8DD
person.identifier.ciencia-id9A1A-43FB-5C27
person.identifier.orcid0000-0003-2706-7777
person.identifier.orcid0000-0002-3924-776X
person.identifier.ridL-3085-2014
person.identifier.ridD-4990-2013
person.identifier.scopus-author-id55232677900
person.identifier.scopus-author-id6603741848
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsopenAccesspt_PT
rcaap.typearticlept_PT
relation.isAuthorOfPublicationaad1737a-79f4-4c05-a480-3c0197877757
relation.isAuthorOfPublication09f6a7bd-2f15-42b0-adc5-04bd22210519
relation.isAuthorOfPublication.latestForDiscovery09f6a7bd-2f15-42b0-adc5-04bd22210519
relation.isProjectOfPublicationa1891cb0-b820-4fd0-bc6c-e8918d4d4ce6
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