Design, Antileishmanial Activity, and QSAR Studies of a Series of Piplartine Analogues
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2019 |
| Outros Autores: | , , , , , , |
| Tipo de documento: | Artigo |
| Idioma: | eng |
| Título da fonte: | Repositório Institucional da FIOCRUZ (ARCA) |
| Texto Completo: | https://www.arca.fiocruz.br/handle/icict/31766 |
Resumo: | Brazilian agencies Conselho Nacional de Desenvolvimento Cient´ıfico e Tecnol´ogico (CNPq) and Coordenação de Aperfeiçoamento de Pessoal de N´ıvel Superior (CAPES) |
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Nóbrega, Flávio RobertoSilva, Larisse VieiraBezerra Filho, Carlos da Silva MaiaLima, Tamires CardosoCastillo, Yunierkis P.Bezerra, Daniel PereiraLima, Tatjana K. SouzaSousa, Damião Pereira de2019-02-19T16:30:11Z2019-02-19T16:30:11Z2019NÓBREGA, F. R. et al. Design, Antileishmanial Activity, and QSAR Studies of a Series of Piplartine Analogues. Journal of Chemistry, p. 1-13, 2019.2090-9063https://www.arca.fiocruz.br/handle/icict/3176610.1155/2019/4785756Brazilian agencies Conselho Nacional de Desenvolvimento Cient´ıfico e Tecnol´ogico (CNPq) and Coordenação de Aperfeiçoamento de Pessoal de N´ıvel Superior (CAPES)Universidade Federal da Paraíba. Laboratory of Pharmaceutical Chemistry. João Pessoa, PB, Brazil.Universidade Federal da Paraíba. Department of Cellular and Molecular Biology. João Pessoa, PB, Brazil.Universidade Federal da Paraíba. Laboratory of Pharmaceutical Chemistry. João Pessoa, PB, Brazil.Federal University of Sergipe. Department of Pharmacy. São Cristóvão, SE, Brazil.Universidad de Las Américas. Escuela de Ciencias Físicas y Matemáticas. Quito, Ecuador.Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Brasil.Universidade Federal da Paraíba. Department of Cellular and Molecular Biology. João Pessoa, PB, Brazil.Universidade Federal da Paraíba. Laboratory of Pharmaceutical Chemistry. João Pessoa, PB, Brazil.Piplartine is an alkamide found in different Piper species and possesses several biological activities, including antiparasitic properties. Thus, the aim of the present study was to evaluate a series of 32 synthetic piplartine analogues against the Leishmania amazonensis promastigote forms and establish the structure-activity relationship and 3D-QSAR of these compounds. The antileishmanial effect of the compounds was determined using the MTTmethod. Most compounds were found to be active against L. amazonensis. Among 32 assayed derivatives, compound (E)-(−)-bornyl 3-(3,4,5-trimethoxyphenyl)-acrylate exhibited the most potent antileishmanial activity (IC50 = 0.007 ± 0.008 μM, SI > 10), followed by benzyl 3,4,5-trimethoxybenzoate (IC50 = 0.025 ± 0.009 μM, SI > 3.205) and (E)-furfuryl 3-(3,4,5-trimethoxyphenyl)-acrylate (IC50 = 0.029 ± 0.007 μM, SI > 2.688). It was found that the rigid substituents contribute to increasing antiparasitic activity against L. amazonensis promastigotes. The presence of the unsaturated heterocyclic substituent in the phenylpropanoid chemical structure (furfuryl group) resulted in a bioactive derivative. Molecular simplification of benzyl 3,4,5- trimethoxybenzoate by omitting the spacer group contributed to the bioactivity of this compound. Furthermore, bornyl radical appears to be important for antileishmanial activity, since (E)-(−)-bornyl 3-(3,4,5-trimethoxyphenyl)-acrylate exhibited the most potent antileishmanial activity. These results show that some derivatives studied would be useful as prototype molecules for the planning of new derivatives with profile of antileishmanial drugs.engHindawi Publishing CorporationLeishmanioseLeishmaniose visceralDrogasAvaliação de MedicamentosPiperLeishmaniasisVisceral leishmaniasisDrugsDrug EvaluationPiperDesign, Antileishmanial Activity, and QSAR Studies of a Series of Piplartine Analoguesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleinfo: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/31766/1/license.txt5a560609d32a3863062d77ff32785d58MD51ORIGINALNóbrega F.R. Design, Antileishmanial Activity...2019.pdfNóbrega F.R. 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| dc.title.pt_BR.fl_str_mv |
Design, Antileishmanial Activity, and QSAR Studies of a Series of Piplartine Analogues |
| title |
Design, Antileishmanial Activity, and QSAR Studies of a Series of Piplartine Analogues |
| spellingShingle |
Design, Antileishmanial Activity, and QSAR Studies of a Series of Piplartine Analogues Nóbrega, Flávio Roberto Leishmaniose Leishmaniose visceral Drogas Avaliação de Medicamentos Piper Leishmaniasis Visceral leishmaniasis Drugs Drug Evaluation Piper |
| title_short |
Design, Antileishmanial Activity, and QSAR Studies of a Series of Piplartine Analogues |
| title_full |
Design, Antileishmanial Activity, and QSAR Studies of a Series of Piplartine Analogues |
| title_fullStr |
Design, Antileishmanial Activity, and QSAR Studies of a Series of Piplartine Analogues |
| title_full_unstemmed |
Design, Antileishmanial Activity, and QSAR Studies of a Series of Piplartine Analogues |
| title_sort |
Design, Antileishmanial Activity, and QSAR Studies of a Series of Piplartine Analogues |
| author |
Nóbrega, Flávio Roberto |
| author_facet |
Nóbrega, Flávio Roberto Silva, Larisse Vieira Bezerra Filho, Carlos da Silva Maia Lima, Tamires Cardoso Castillo, Yunierkis P. Bezerra, Daniel Pereira Lima, Tatjana K. Souza Sousa, Damião Pereira de |
| author_role |
author |
| author2 |
Silva, Larisse Vieira Bezerra Filho, Carlos da Silva Maia Lima, Tamires Cardoso Castillo, Yunierkis P. Bezerra, Daniel Pereira Lima, Tatjana K. Souza Sousa, Damião Pereira de |
| author2_role |
author author author author author author author |
| dc.contributor.author.fl_str_mv |
Nóbrega, Flávio Roberto Silva, Larisse Vieira Bezerra Filho, Carlos da Silva Maia Lima, Tamires Cardoso Castillo, Yunierkis P. Bezerra, Daniel Pereira Lima, Tatjana K. Souza Sousa, Damião Pereira de |
| dc.subject.other.pt_BR.fl_str_mv |
Leishmaniose Leishmaniose visceral Drogas Avaliação de Medicamentos Piper |
| topic |
Leishmaniose Leishmaniose visceral Drogas Avaliação de Medicamentos Piper Leishmaniasis Visceral leishmaniasis Drugs Drug Evaluation Piper |
| dc.subject.en.pt_BR.fl_str_mv |
Leishmaniasis Visceral leishmaniasis Drugs Drug Evaluation Piper |
| description |
Brazilian agencies Conselho Nacional de Desenvolvimento Cient´ıfico e Tecnol´ogico (CNPq) and Coordenação de Aperfeiçoamento de Pessoal de N´ıvel Superior (CAPES) |
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2019 |
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2019-02-19T16:30:11Z |
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2019-02-19T16:30:11Z |
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2019 |
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info:eu-repo/semantics/publishedVersion |
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info:eu-repo/semantics/article |
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NÓBREGA, F. R. et al. Design, Antileishmanial Activity, and QSAR Studies of a Series of Piplartine Analogues. Journal of Chemistry, p. 1-13, 2019. |
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https://www.arca.fiocruz.br/handle/icict/31766 |
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2090-9063 |
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10.1155/2019/4785756 |
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NÓBREGA, F. R. et al. Design, Antileishmanial Activity, and QSAR Studies of a Series of Piplartine Analogues. Journal of Chemistry, p. 1-13, 2019. 2090-9063 10.1155/2019/4785756 |
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Hindawi Publishing Corporation |
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Hindawi Publishing Corporation |
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