Synthesis of piplartine analogs and preliminary findings on structure–antimicrobial activity relationship
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2017 |
| 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/26031 |
Resumo: | FAPEMIG (APQ-01209-13), CAPES, CNPq and FINEP. |
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Fregnan, Antonio MacielBrancaglion, Guilherme AndradeGalvão, Alexandre Francisco CerqueiraCosta, Cinara Oliveira D’SousaMoreira, Diogo Rodrigo MagalhãesSoares, Milena Botelho PereiraBezerra, Daniel PereiraSilva, Naiara ChavesMorais, Stella Maria de SouzaOliver, Josidel ConceiçãoDias, Amanda Latercia TranchesCoelho, Luiz Felipe LeomilCarvalho, Diogo TeixeiraDias, Danielle FerreiraSouza, Thiago Belarmino de2018-04-23T14:32:48Z2018-04-23T14:32:48Z2017FREGNAN, A. M. et al. Synthesis of piplartine analogs and preliminary findings on structure–antimicrobial activity relationship. Medicinal Chemistry Research, v. 26, p. 603–614, 2017.1054-2523https://www.arca.fiocruz.br/handle/icict/26031FAPEMIG (APQ-01209-13), CAPES, CNPq and FINEP.Universidade Federal de Alfenas. Faculdade de Ciências Farmacêuticas. Alfenas, MG, BrasilUniversidade Federal de Alfenas. Instituto de Química. Alfenas, MG, BrasilFundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, BrasilFundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, BrasilFundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, Brasil / Hospital São Rafael. Centro de Biotecnologia e Terapia Celular. Salvador, BA, BrasilFundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, Brasil / Hospital São Rafael. Centro de Biotecnologia e Terapia Celular. Salvador, BA, BrasilFundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, BrasilUniversidade Federal de Alfenas. Instituto de Ciências Biomédicas. Alfenas, MG, BrasilUniversidade Federal de Alfenas. Instituto de Ciências Biomédicas. Alfenas, MG, BrasilUniversidade Federal de Alfenas. Instituto de Ciências Biomédicas. Alfenas, MG, BrasilUniversidade Federal de Alfenas. Instituto de Ciências Biomédicas. Alfenas, MG, BrasilUniversidade Federal de Alfenas. Instituto de Ciências Biomédicas. Alfenas, MG, BrasilUniversidade Federal de Alfenas. Faculdade de Ciências Farmacêuticas. Alfenas, MG, BrasilUniversidade Federal de Alfenas. Instituto de Química. Alfenas, MG, BrasilUniversidade Federal de Alfenas. Instituto de Química. Alfenas, MG, BrasilAbstract In this work it is described the synthesis, characterization and antimicrobial and toxicity evaluation of a series of analogs of piplartine, a piperamide found in Piper sp. The compounds structures were confirmed by infrared spectroscopy, 1H, 13C nuclear magnetic resonance, high resolution mass spectroscopy and were evaluated against strains of Candida spp., Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa. Derivative 24 was almost four-fold more potent (IC50: 48.83 μM) and five-fold less toxic (SI > 3) than piplartine (IC50: 189.2 μM; SI: 0.21) against Candida krusei, as well as two-fold more potent than fluconazole (IC50: 104.48 μM). This compound was also active against Candida tropicalis at 97.67 μM. Benzoyl derivative 17 was three-fold more potent (IC50: 85.2 μM) and more than five-fold less toxic (CC50: 231.71 μM) than piplartine (IC50: 315.33 μM and CC50: 41.14 μM) against Staphylococcus aureus. Given these findings, we have found analogs of piplartine which can be assumed as prototypes for the optimization and the development of new antimicrobial (compounds 24 and 17) agents.engSpringer VerlagPiplartinaAnálogosAtividade antifúngicaAtividade antibacterianaPiplartineAnalogsAntifungal activityAntibacterial activitySynthesis of piplartine analogs and preliminary findings on structure–antimicrobial activity relationshipinfo: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/26031/1/license.txt5a560609d32a3863062d77ff32785d58MD51ORIGINALFregnam AM Synthesis of piplartine.pdfFregnam AM Synthesis of piplartine.pdfapplication/pdf1853217https://www.arca.fiocruz.br/bitstream/icict/26031/2/Fregnam%20AM%20Synthesis%20of%20piplartine.pdf194ed12d0c7b2d0823762280877833faMD52TEXTFregnam AM Synthesis of piplartine.pdf.txtFregnam AM Synthesis of piplartine.pdf.txtExtracted texttext/plain49549https://www.arca.fiocruz.br/bitstream/icict/26031/3/Fregnam%20AM%20Synthesis%20of%20piplartine.pdf.txt92e4fd486255eba771dff30928d500f1MD53icict/260312023-03-15 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| dc.title.pt_BR.fl_str_mv |
Synthesis of piplartine analogs and preliminary findings on structure–antimicrobial activity relationship |
| title |
Synthesis of piplartine analogs and preliminary findings on structure–antimicrobial activity relationship |
| spellingShingle |
Synthesis of piplartine analogs and preliminary findings on structure–antimicrobial activity relationship Fregnan, Antonio Maciel Piplartina Análogos Atividade antifúngica Atividade antibacteriana Piplartine Analogs Antifungal activity Antibacterial activity |
| title_short |
Synthesis of piplartine analogs and preliminary findings on structure–antimicrobial activity relationship |
| title_full |
Synthesis of piplartine analogs and preliminary findings on structure–antimicrobial activity relationship |
| title_fullStr |
Synthesis of piplartine analogs and preliminary findings on structure–antimicrobial activity relationship |
| title_full_unstemmed |
Synthesis of piplartine analogs and preliminary findings on structure–antimicrobial activity relationship |
| title_sort |
Synthesis of piplartine analogs and preliminary findings on structure–antimicrobial activity relationship |
| author |
Fregnan, Antonio Maciel |
| author_facet |
Fregnan, Antonio Maciel Brancaglion, Guilherme Andrade Galvão, Alexandre Francisco Cerqueira Costa, Cinara Oliveira D’Sousa Moreira, Diogo Rodrigo Magalhães Soares, Milena Botelho Pereira Bezerra, Daniel Pereira Silva, Naiara Chaves Morais, Stella Maria de Souza Oliver, Josidel Conceição Dias, Amanda Latercia Tranches Coelho, Luiz Felipe Leomil Carvalho, Diogo Teixeira Dias, Danielle Ferreira Souza, Thiago Belarmino de |
| author_role |
author |
| author2 |
Brancaglion, Guilherme Andrade Galvão, Alexandre Francisco Cerqueira Costa, Cinara Oliveira D’Sousa Moreira, Diogo Rodrigo Magalhães Soares, Milena Botelho Pereira Bezerra, Daniel Pereira Silva, Naiara Chaves Morais, Stella Maria de Souza Oliver, Josidel Conceição Dias, Amanda Latercia Tranches Coelho, Luiz Felipe Leomil Carvalho, Diogo Teixeira Dias, Danielle Ferreira Souza, Thiago Belarmino de |
| author2_role |
author author author author author author author author author author author author author author |
| dc.contributor.author.fl_str_mv |
Fregnan, Antonio Maciel Brancaglion, Guilherme Andrade Galvão, Alexandre Francisco Cerqueira Costa, Cinara Oliveira D’Sousa Moreira, Diogo Rodrigo Magalhães Soares, Milena Botelho Pereira Bezerra, Daniel Pereira Silva, Naiara Chaves Morais, Stella Maria de Souza Oliver, Josidel Conceição Dias, Amanda Latercia Tranches Coelho, Luiz Felipe Leomil Carvalho, Diogo Teixeira Dias, Danielle Ferreira Souza, Thiago Belarmino de |
| dc.subject.other.pt_BR.fl_str_mv |
Piplartina Análogos Atividade antifúngica Atividade antibacteriana |
| topic |
Piplartina Análogos Atividade antifúngica Atividade antibacteriana Piplartine Analogs Antifungal activity Antibacterial activity |
| dc.subject.en.pt_BR.fl_str_mv |
Piplartine Analogs Antifungal activity Antibacterial activity |
| description |
FAPEMIG (APQ-01209-13), CAPES, CNPq and FINEP. |
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2017 |
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2017 |
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2018-04-23T14:32:48Z |
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2018-04-23T14:32:48Z |
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info:eu-repo/semantics/publishedVersion |
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info:eu-repo/semantics/article |
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article |
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publishedVersion |
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FREGNAN, A. M. et al. Synthesis of piplartine analogs and preliminary findings on structure–antimicrobial activity relationship. Medicinal Chemistry Research, v. 26, p. 603–614, 2017. |
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https://www.arca.fiocruz.br/handle/icict/26031 |
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1054-2523 |
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FREGNAN, A. M. et al. Synthesis of piplartine analogs and preliminary findings on structure–antimicrobial activity relationship. Medicinal Chemistry Research, v. 26, p. 603–614, 2017. 1054-2523 |
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Springer Verlag |
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Springer Verlag |
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