Flavopereirine-An Alkaloid Derived from Geissospermum vellosii-Presents Leishmanicidal Activity In Vitro

Detalhes bibliográficos
Autor(a) principal: Silva, João Victor da Silva e
Data de Publicação: 2019
Outros Autores: Brigido, Heliton Patrick Cordovil, Albuquerque, Kelly Cristina Oliveira de, Carvalho, Josiwander Miranda, Reis, Jordano Ferreira, Faria, Lara Vinhal, Ferreira, Márlia Coelho, Silveira, Fernando Tobias, Carneiro, Agnaldo da Silva, Percário, Sandro, Marinho, Andrey Moacir do Rosário, Dolabela, Maria Fâni
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da FIOCRUZ (ARCA)
Texto Completo: https://www.arca.fiocruz.br/handle/icict/32902
Resumo: Universidade Federal do Pará. Programa de Pós-Graduação em Ciências Farmacêuticas. Belém, PA, Brasil / Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Imunomodulação e Protozoologia. Rio de Janeiro, RJ, Brasil.
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spelling Silva, João Victor da Silva eBrigido, Heliton Patrick CordovilAlbuquerque, Kelly Cristina Oliveira deCarvalho, Josiwander MirandaReis, Jordano FerreiraFaria, Lara VinhalFerreira, Márlia CoelhoSilveira, Fernando TobiasCarneiro, Agnaldo da SilvaPercário, SandroMarinho, Andrey Moacir do RosárioDolabela, Maria Fâni2019-05-02T12:17:41Z2019-05-02T12:17:41Z2019SILVA, João Victor da Silva e et al. Flavopereirine—An Alkaloid Derived from Geissospermum vellosii—Presents Leishmanicidal Activity In Vitro. Molecules, v. 24, n. 785, 13p, 2019.1420-3049https://www.arca.fiocruz.br/handle/icict/3290210.3390/molecules24040785engMDPILeishmaniaQuímica MedicinalModelagem in silicoApocynaceaeLeishmaniaGeissospermum vellosiiApocynaceaeOligopeptidase BFlavopereirineMedicinal chemistryIn silico modelingFlavopereirine-An Alkaloid Derived from Geissospermum vellosii-Presents Leishmanicidal Activity In Vitroinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleUniversidade Federal do Pará. Programa de Pós-Graduação em Ciências Farmacêuticas. Belém, PA, Brasil / Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Imunomodulação e Protozoologia. Rio de Janeiro, RJ, Brasil.Universidade Federal do Pará. Programa de Pós-Graduação em Inovação Farmacêutica. Belém, PA, Brasil.Universidade Federal do Pará. Programa de Pós-Graduação em Ciências Farmacêuticas. Belém, PA, Brasil.Universidade Federal do Pará. Faculdade de Química. Belém, PA, Brasil.Universidade Federal do Pará. Faculdade de Farmácia. Belém, PA, Brasil.Universidade Federal do Pará. Faculdade de Farmácia. Belém, PA, Brasil.Ministério da Ciência, Tecnologia, Inovação e Comunicações. Coordenação de Botânica. Museu Paraense Emílio Goeldi. Belém, PA, Brasil.Fundação Nacional de Saúde. Instituto Evandro Chagas. Belém, PA, Brasil.Universidade Federal do Pará. Faculdade de Farmácia. Belém, PA, Brasil.US Centers for Disease Control and Prevention. Atlanta, GA, USA / Universidade Federal do Pará. Instituto de Ciências Biológicas. Laboratório de Pesquisa do Estresse Oxidativo. Belém, PA, Brasil.Universidade Federal do Pará. Faculdade de Química. Belém, PA, Brasil.Universidade Federal do Pará. Programa de Pós-Graduação em Ciências Farmacêuticas. Belém, PA, Brasil / Universidade Federal do Pará. Programa de Pós-Graduação em Inovação Farmacêutica. Belém, PA, Brasil.Chemotherapy is limited in the treatment of leishmaniasis due to the toxic effects of drugs, low efficacy of alternative treatments, and resistance of the parasite. This work assesses the in vitro activity of flavopereirine on promastigote cultures of Leishmania amazonensis. In addition, an in silico evaluation of the physicochemical characteristics of this alkaloid is performed. The extract and fractions were characterized by thin-layer chromatography and HPLC-DAD, yielding an alkaloid identified by NMR. The antileishmanial activity and cytotoxicity were assayed by cell viability test (MTT). The theoretical molecular properties were calculated on the Molinspiration website. The fractionation made it possible to isolate a beta-carboline alkaloid (flavopereirine) in the alkaloid fraction. Moreover, it led to obtaining a fraction with greater antileishmanial activity, since flavopereirine is very active. Regarding the exposure time, a greater inhibitory effect of flavopereirine was observed at 24 h and 72 h (IC50 of 0.23 and 0.15 μg/mL, respectively). The extract, fractions, and flavopereirine presented low toxicity, with high selectivity for the alkaloid. Furthermore, flavopereirine showed no violation of Lipinski's rule of five, showing even better results than the known inhibitor of oligopeptidase B, antipain, with three violations. Flavopereirine also interacted with residue Tyr-499 of oligopeptidase B during the molecular dynamics simulations, giving a few insights of a possible favorable mechanism of interaction and a possible inhibitory pathway. Flavopereirine proved to be a promising molecule for its antileishmanial activity.info:eu-repo/semantics/openAccessreponame:Repositório Institucional da FIOCRUZ (ARCA)instname:Fundação Oswaldo Cruz (FIOCRUZ)instacron:FIOCRUZLICENSElicense.txtlicense.txttext/plain; charset=utf-82991https://www.arca.fiocruz.br/bitstream/icict/32902/1/license.txt5a560609d32a3863062d77ff32785d58MD51ORIGINALJoâoVitorSSilva_KellyCOAlbuquerque_etal_IOC_2019.pdfJoâoVitorSSilva_KellyCOAlbuquerque_etal_IOC_2019.pdfapplication/pdf1841323https://www.arca.fiocruz.br/bitstream/icict/32902/2/Jo%c3%a2oVitorSSilva_KellyCOAlbuquerque_etal_IOC_2019.pdf245624bea1ca37b15611389a5ec7507bMD52TEXTJoâoVitorSSilva_KellyCOAlbuquerque_etal_IOC_2019.pdf.txtJoâoVitorSSilva_KellyCOAlbuquerque_etal_IOC_2019.pdf.txtExtracted texttext/plain55403https://www.arca.fiocruz.br/bitstream/icict/32902/3/Jo%c3%a2oVitorSSilva_KellyCOAlbuquerque_etal_IOC_2019.pdf.txt002fe83c7949d0b9af4bac705c129b16MD53icict/329022019-05-03 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dc.title.pt_BR.fl_str_mv Flavopereirine-An Alkaloid Derived from Geissospermum vellosii-Presents Leishmanicidal Activity In Vitro
title Flavopereirine-An Alkaloid Derived from Geissospermum vellosii-Presents Leishmanicidal Activity In Vitro
spellingShingle Flavopereirine-An Alkaloid Derived from Geissospermum vellosii-Presents Leishmanicidal Activity In Vitro
Silva, João Victor da Silva e
Leishmania
Química Medicinal
Modelagem in silico
Apocynaceae
Leishmania
Geissospermum vellosii
Apocynaceae
Oligopeptidase B
Flavopereirine
Medicinal chemistry
In silico modeling
title_short Flavopereirine-An Alkaloid Derived from Geissospermum vellosii-Presents Leishmanicidal Activity In Vitro
title_full Flavopereirine-An Alkaloid Derived from Geissospermum vellosii-Presents Leishmanicidal Activity In Vitro
title_fullStr Flavopereirine-An Alkaloid Derived from Geissospermum vellosii-Presents Leishmanicidal Activity In Vitro
title_full_unstemmed Flavopereirine-An Alkaloid Derived from Geissospermum vellosii-Presents Leishmanicidal Activity In Vitro
title_sort Flavopereirine-An Alkaloid Derived from Geissospermum vellosii-Presents Leishmanicidal Activity In Vitro
author Silva, João Victor da Silva e
author_facet Silva, João Victor da Silva e
Brigido, Heliton Patrick Cordovil
Albuquerque, Kelly Cristina Oliveira de
Carvalho, Josiwander Miranda
Reis, Jordano Ferreira
Faria, Lara Vinhal
Ferreira, Márlia Coelho
Silveira, Fernando Tobias
Carneiro, Agnaldo da Silva
Percário, Sandro
Marinho, Andrey Moacir do Rosário
Dolabela, Maria Fâni
author_role author
author2 Brigido, Heliton Patrick Cordovil
Albuquerque, Kelly Cristina Oliveira de
Carvalho, Josiwander Miranda
Reis, Jordano Ferreira
Faria, Lara Vinhal
Ferreira, Márlia Coelho
Silveira, Fernando Tobias
Carneiro, Agnaldo da Silva
Percário, Sandro
Marinho, Andrey Moacir do Rosário
Dolabela, Maria Fâni
author2_role author
author
author
author
author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Silva, João Victor da Silva e
Brigido, Heliton Patrick Cordovil
Albuquerque, Kelly Cristina Oliveira de
Carvalho, Josiwander Miranda
Reis, Jordano Ferreira
Faria, Lara Vinhal
Ferreira, Márlia Coelho
Silveira, Fernando Tobias
Carneiro, Agnaldo da Silva
Percário, Sandro
Marinho, Andrey Moacir do Rosário
Dolabela, Maria Fâni
dc.subject.other.pt_BR.fl_str_mv Leishmania
Química Medicinal
Modelagem in silico
Apocynaceae
topic Leishmania
Química Medicinal
Modelagem in silico
Apocynaceae
Leishmania
Geissospermum vellosii
Apocynaceae
Oligopeptidase B
Flavopereirine
Medicinal chemistry
In silico modeling
dc.subject.en.pt_BR.fl_str_mv Leishmania
Geissospermum vellosii
Apocynaceae
Oligopeptidase B
Flavopereirine
Medicinal chemistry
In silico modeling
description Universidade Federal do Pará. Programa de Pós-Graduação em Ciências Farmacêuticas. Belém, PA, Brasil / Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Imunomodulação e Protozoologia. Rio de Janeiro, RJ, Brasil.
publishDate 2019
dc.date.accessioned.fl_str_mv 2019-05-02T12:17:41Z
dc.date.available.fl_str_mv 2019-05-02T12:17:41Z
dc.date.issued.fl_str_mv 2019
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.citation.fl_str_mv SILVA, João Victor da Silva e et al. Flavopereirine—An Alkaloid Derived from Geissospermum vellosii—Presents Leishmanicidal Activity In Vitro. Molecules, v. 24, n. 785, 13p, 2019.
dc.identifier.uri.fl_str_mv https://www.arca.fiocruz.br/handle/icict/32902
dc.identifier.issn.pt_BR.fl_str_mv 1420-3049
dc.identifier.doi.none.fl_str_mv 10.3390/molecules24040785
identifier_str_mv SILVA, João Victor da Silva e et al. Flavopereirine—An Alkaloid Derived from Geissospermum vellosii—Presents Leishmanicidal Activity In Vitro. Molecules, v. 24, n. 785, 13p, 2019.
1420-3049
10.3390/molecules24040785
url https://www.arca.fiocruz.br/handle/icict/32902
dc.language.iso.fl_str_mv eng
language eng
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv MDPI
publisher.none.fl_str_mv MDPI
dc.source.none.fl_str_mv reponame:Repositório Institucional da FIOCRUZ (ARCA)
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collection Repositório Institucional da FIOCRUZ (ARCA)
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