The compound (E)-2-cyano-N,3-diphenylacrylamide (JMPR-01): a potential drug for treatment of inflammatory diseases

Detalhes bibliográficos
Autor(a) principal: Silva, Pablo Rayff da
Data de Publicação: 2023
Outros Autores: Espírito Santo, Renan Fernandes do, Melo, Camila de Oliveira, Cavalcante, Fábio Emanuel Pachú, Costa, Thássia Borges, Barbosa, Yasmim Vilarim, Silva, Yvnni M. S. de Medeiros e, Sousa, Natália Ferreira de, Villarreal, Cristiane Flora, Moura, Ricardo Olímpio de, Santos, Vanda Lucia dos
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da FIOCRUZ (ARCA)
Texto Completo: https://www.arca.fiocruz.br/handle/icict/60894
Resumo: Fundação de Amparo à Pesquisa do Estado da Paraíba (FAPESQ). Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (Capes).
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spelling Silva, Pablo Rayff daEspírito Santo, Renan Fernandes doMelo, Camila de OliveiraCavalcante, Fábio Emanuel PachúCosta, Thássia BorgesBarbosa, Yasmim VilarimSilva, Yvnni M. S. de Medeiros eSousa, Natália Ferreira deVillarreal, Cristiane FloraMoura, Ricardo Olímpio deSantos, Vanda Lucia dos2023-10-24T17:52:54Z2023-10-24T17:52:54Z2023SILVA, Pablo Rayff da et al. The compound (E)-2-Cyano-N,3-diphenylacrylamide (JMPR-01): a potential drug for treatment of inflammatory diseases. Pharmaceutics, v.14, n. 1, p. 1-21, 2022.1999-4923https://www.arca.fiocruz.br/handle/icict/6089410.3390/pharmaceutics14010188Fundação de Amparo à Pesquisa do Estado da Paraíba (FAPESQ). Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (Capes).Universidade Estadual da Paraíba. Programa de Pós-graduação em Ciências Farmacêuticas. Campina Grande, PB, Brasil / Universidade Estadual da Paraíba. Laboratório de Ensaios Farmacológicos. Departamento de Farmácia. Campina Grande, PB, Brasil / Universidade Estadual da Paraíba. Departamento de Farmácia. Laboratório de Desenvolvimento e Síntese de Fármacos. Campina Grande, PB, Brasil.Fundação Osvaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Brasil / Universidade Federal da Bahia. Faculdade de Farmácia. Salvador, BA, Brasil.Universidade Estadual da Paraíba. Programa de Pós-graduação em Ciências Farmacêuticas. Campina Grande, PB, Brasil / Universidade Estadual da Paraíba. Departamento de Farmácia. Laboratório de Desenvolvimento e Síntese de Fármacos. Campina Grande, PB, Brasil.Universidade Estadual da Paraíba. Laboratório de Ensaios Farmacológicos. Departamento de Farmácia. Campina Grande, PB, Brasil.Universidade Estadual da Paraíba. Laboratório de Ensaios Farmacológicos. Departamento de Farmácia. Campina Grande, PB, Brasil.Universidade Estadual da Paraíba. Laboratório de Ensaios Farmacológicos. Departamento de Farmácia. Campina Grande, PB, Brasil.Universidade Estadual da Paraíba. Departamento de Farmácia. Laboratório de Desenvolvimento e Síntese de Fármacos. Campina Grande, PB, Brasil.Universidade Federal da Paraíba. Programa de Pós-graduação em Produtos Naturais, Sintéticos e Bioativos. João Pessoa, PB, Brasil.Fundação Osvaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Brasil / Universidade Federal da Bahia. Faculdade de Farmácia. Salvador, BA, Brasil.Universidade Estadual da Paraíba. Programa de Pós-graduação em Ciências Farmacêuticas. Campina Grande, PB, Brasil / Universidade Estadual da Paraíba. Departamento de Farmácia. Laboratório de Desenvolvimento e Síntese de Fármacos. Campina Grande, PB, Brasil.Universidade Estadual da Paraíba. Programa de Pós-graduação em Ciências Farmacêuticas. Campina Grande, PB, Brasil / Universidade Estadual da Paraíba. Laboratório de Ensaios Farmacológicos. Departamento de Farmácia. Campina Grande, PB, Brasil.The compound (E)-2-cyano-N,3-diphenylacrylamide (JMPR-01) was structurally developed using bioisosteric modifications of a hybrid prototype as formed from fragments of indomethacin and paracetamol. Initially, in vitro assays were performed to determine cell viability (in macrophage cultures), and its ability to modulate the synthesis of nitrite and cytokines (IL-1β and TNFα) in non-cytotoxic concentrations. In vivo, anti-inflammatory activity was explored using the CFA-induced paw edema and zymosan-induced peritonitis models. To investigate possible molecular targets, molecular docking was performed with the following crystallographic structures: LT-A4-H, PDE4B, COX-2, 5-LOX, and iNOS. As results, we observed a significant reduction in the production of nitrite and IL-1β at all concentrations used, and also for TNFα with JMPR-01 at 50 and 25 μM. The anti-edematogenic activity of JMPR-01 (100 mg/kg) was significant, reducing edema at 2–6 h, similar to the dexamethasone control. In induced peritonitis, JMPR-01 reduced leukocyte migration by 61.8, 68.5, and 90.5% at respective doses of 5, 10, and 50 mg/kg. In silico, JMPR-01 presented satisfactory coupling; mainly with LT-A4-H, PDE4B, and iNOS. These preliminary results demonstrate the strong potential of JMPR-01 to become a drug for the treatment of inflammatory diseases.engMDPIBioisosterismoFenilacrilamidaImunomodulaçãoInflamaçãoBioisosterismPhenylacrylamideImmunomodulationInflammationImunomodulaçãoInflamaçãoThe compound (E)-2-cyano-N,3-diphenylacrylamide (JMPR-01): a potential drug for treatment of inflammatory diseasesinfo: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/60894/1/license.txt5a560609d32a3863062d77ff32785d58MD51ORIGINALVillarreal, C. F. - The Compound.pdfVillarreal, C. F. - The Compound.pdfapplication/pdf35453259https://www.arca.fiocruz.br/bitstream/icict/60894/2/Villarreal%2c%20C.%20F.%20-%20The%20Compound.pdfc980332b3bb9398e6c3ffbb452f6e1a5MD52icict/608942023-10-24 14:52:55.601oai:www.arca.fiocruz.br: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ório InstitucionalPUBhttps://www.arca.fiocruz.br/oai/requestrepositorio.arca@fiocruz.bropendoar:21352023-10-24T17:52:55Repositório Institucional da FIOCRUZ (ARCA) - Fundação Oswaldo Cruz (FIOCRUZ)false
dc.title.en_US.fl_str_mv The compound (E)-2-cyano-N,3-diphenylacrylamide (JMPR-01): a potential drug for treatment of inflammatory diseases
title The compound (E)-2-cyano-N,3-diphenylacrylamide (JMPR-01): a potential drug for treatment of inflammatory diseases
spellingShingle The compound (E)-2-cyano-N,3-diphenylacrylamide (JMPR-01): a potential drug for treatment of inflammatory diseases
Silva, Pablo Rayff da
Bioisosterismo
Fenilacrilamida
Imunomodulação
Inflamação
Bioisosterism
Phenylacrylamide
Immunomodulation
Inflammation
Imunomodulação
Inflamação
title_short The compound (E)-2-cyano-N,3-diphenylacrylamide (JMPR-01): a potential drug for treatment of inflammatory diseases
title_full The compound (E)-2-cyano-N,3-diphenylacrylamide (JMPR-01): a potential drug for treatment of inflammatory diseases
title_fullStr The compound (E)-2-cyano-N,3-diphenylacrylamide (JMPR-01): a potential drug for treatment of inflammatory diseases
title_full_unstemmed The compound (E)-2-cyano-N,3-diphenylacrylamide (JMPR-01): a potential drug for treatment of inflammatory diseases
title_sort The compound (E)-2-cyano-N,3-diphenylacrylamide (JMPR-01): a potential drug for treatment of inflammatory diseases
author Silva, Pablo Rayff da
author_facet Silva, Pablo Rayff da
Espírito Santo, Renan Fernandes do
Melo, Camila de Oliveira
Cavalcante, Fábio Emanuel Pachú
Costa, Thássia Borges
Barbosa, Yasmim Vilarim
Silva, Yvnni M. S. de Medeiros e
Sousa, Natália Ferreira de
Villarreal, Cristiane Flora
Moura, Ricardo Olímpio de
Santos, Vanda Lucia dos
author_role author
author2 Espírito Santo, Renan Fernandes do
Melo, Camila de Oliveira
Cavalcante, Fábio Emanuel Pachú
Costa, Thássia Borges
Barbosa, Yasmim Vilarim
Silva, Yvnni M. S. de Medeiros e
Sousa, Natália Ferreira de
Villarreal, Cristiane Flora
Moura, Ricardo Olímpio de
Santos, Vanda Lucia dos
author2_role author
author
author
author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Silva, Pablo Rayff da
Espírito Santo, Renan Fernandes do
Melo, Camila de Oliveira
Cavalcante, Fábio Emanuel Pachú
Costa, Thássia Borges
Barbosa, Yasmim Vilarim
Silva, Yvnni M. S. de Medeiros e
Sousa, Natália Ferreira de
Villarreal, Cristiane Flora
Moura, Ricardo Olímpio de
Santos, Vanda Lucia dos
dc.subject.other.en_US.fl_str_mv Bioisosterismo
Fenilacrilamida
Imunomodulação
Inflamação
topic Bioisosterismo
Fenilacrilamida
Imunomodulação
Inflamação
Bioisosterism
Phenylacrylamide
Immunomodulation
Inflammation
Imunomodulação
Inflamação
dc.subject.en.en_US.fl_str_mv Bioisosterism
Phenylacrylamide
Immunomodulation
Inflammation
dc.subject.decs.en_US.fl_str_mv Imunomodulação
Inflamação
description Fundação de Amparo à Pesquisa do Estado da Paraíba (FAPESQ). Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (Capes).
publishDate 2023
dc.date.accessioned.fl_str_mv 2023-10-24T17:52:54Z
dc.date.available.fl_str_mv 2023-10-24T17:52:54Z
dc.date.issued.fl_str_mv 2023
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, Pablo Rayff da et al. The compound (E)-2-Cyano-N,3-diphenylacrylamide (JMPR-01): a potential drug for treatment of inflammatory diseases. Pharmaceutics, v.14, n. 1, p. 1-21, 2022.
dc.identifier.uri.fl_str_mv https://www.arca.fiocruz.br/handle/icict/60894
dc.identifier.issn.en_US.fl_str_mv 1999-4923
dc.identifier.doi.none.fl_str_mv 10.3390/pharmaceutics14010188
identifier_str_mv SILVA, Pablo Rayff da et al. The compound (E)-2-Cyano-N,3-diphenylacrylamide (JMPR-01): a potential drug for treatment of inflammatory diseases. Pharmaceutics, v.14, n. 1, p. 1-21, 2022.
1999-4923
10.3390/pharmaceutics14010188
url https://www.arca.fiocruz.br/handle/icict/60894
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)
instname:Fundação Oswaldo Cruz (FIOCRUZ)
instacron:FIOCRUZ
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collection Repositório Institucional da FIOCRUZ (ARCA)
bitstream.url.fl_str_mv https://www.arca.fiocruz.br/bitstream/icict/60894/1/license.txt
https://www.arca.fiocruz.br/bitstream/icict/60894/2/Villarreal%2c%20C.%20F.%20-%20The%20Compound.pdf
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