Molecular hybridization strategy on the design, synthesis, and structural characterization of ferrocene-n-acyl hydrazones as immunomodulatory agents
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2022 |
| 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/56995 |
Resumo: | Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq). Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP). Programa de Apoio a Núcleos de Excelência (Pronex). |
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Silva, Laís PeresSantos, Ivanilson PimentaSilva, Dahara Keyse CarvalhoReis, Bruna Padilha Zurita Claro dosMeira, Cássio SantanaCastro, Marcos Venícius Batista de SouzaSantos Filho, José Maurício dosAraujo Neto, João Honorato deEllena, Javier AlcidesSilveira, Rafael Gomes daSoares, Milena Botelho Pereira2023-02-09T19:43:50Z2023-02-09T19:43:50Z2022SILVA, Laís Peres et al. Molecular hybridization strategy on the design, synthesis, and structural characterization of ferrocene-n-acyl hydrazones as immunomodulatory agents. Molecules, v. 27, p. 1-22, 2022.1420-3049https://www.arca.fiocruz.br/handle/icict/5699510.3390/molecules27238343Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq). Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP). Programa de Apoio a Núcleos de Excelência (Pronex).Universidade Estadual da Bahia. Departamento de Ciências da Vida. Salvador, BA, Brasil.Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Brasil.Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Brasil.Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Brasil.Universidade Estadual da Bahia. Departamento de Ciências da Vida. Salvador, BA, Brasil / Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Brasil / Instituto de Inovação em Sistemas Avançados de Saúda. Centro Universitário SENAI/CIMATEC. Salvador, BA, Brasil.Universidade Federal de Pernambuco. Centro de Tecnologia e Geociências. Laboratório de Desenho e Síntese Aplicada à Química Medicinal-SintMed. Recife, PE, Brasil.Universidade Federal de Pernambuco. Centro de Tecnologia e Geociências. Laboratório de Desenho e Síntese Aplicada à Química Medicinal-SintMed. Recife, PE, Brasil.Universidade de São Paulo. Instituto de São Carlos. Laboratório Multiusuário de Cristalografia Estrutural. São Carlos, SP, Brasil.Universidade de São Paulo. Instituto de São Carlos. Laboratório Multiusuário de Cristalografia Estrutural. São Carlos, SP, Brasil.Universidade de São Paulo. Instituto de São Carlos. Laboratório Multiusuário de Cristalografia Estrutural. São Carlos, SP, Brasil / Instituto Federal de Goiás. Departamento de Química. Ceres, GO, Brasil.Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Brasil / Instituto de Inovação em Sistemas Avançados de Saúda. Centro Universitário SENAI/CIMATEC. Salvador, BA, Brasil.Immunomodulatory agents are widely used for the treatment of immune-mediated diseases, but the range of side effects of the available drugs makes necessary the search for new immunomodulatory drugs. Here, we investigated the immunomodulatory activity of new ferrocenyl-N-acyl hydrazones derivatives (SintMed(141–156). The evaluated N-acyl hydrazones did not show cytotoxicity at the tested concentrations, presenting CC50 values greater than 50 µM. In addition, all ferrocenyl-N-acyl hydrazones modulated nitrite production in immortalized macrophages, showing inhibition values between 14.4% and 74.2%. By presenting a better activity profile, the ferrocenyl-N-acyl hydrazones SintMed149 and SintMed150 also had their cytotoxicity and anti-inflammatory effect evaluated in cultures of peritoneal macrophages. The molecules were not cytotoxic at any of the concentrations tested in peritoneal macrophages and were able to significantly reduce (p < 0.05) the production of nitrite, TNF-α, and IL-1β. Interestingly, both molecules significantly reduced the production of IL-2 and IFN-γ in cultured splenocytes activated with concanavalin A. Moreover, SintMed150 did not show signs of acute toxicity in animals treated with 50 or 100 mg/kg. Finally, we observed that ferrocenyl-N-acyl hydrazone SintMed150 at 100 mg/kg reduced the migration of neutrophils (44.6%) in an acute peritonitis model and increased animal survival by 20% in an LPS-induced endotoxic shock model. These findings suggest that such compounds have therapeutic potential to be used to treat diseases of inflammatory origin.engMDPIImmunomodulationImunomodulaçãoChoque endotóxicoPeritonite agudaN-acil hidrazonasFerrocenoImmunomodulationEndotoxic shockAcute peritonitisN-acyl hydrazonesferroceneMolecular hybridization strategy on the design, synthesis, and structural characterization of ferrocene-n-acyl hydrazones as immunomodulatory agentsinfo: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/56995/1/license.txt5a560609d32a3863062d77ff32785d58MD51ORIGINALSilva, L.P. Molecular Hybridization Strategy...2022.pdfSilva, L.P. Molecular Hybridization Strategy...2022.pdfapplication/pdf4315740https://www.arca.fiocruz.br/bitstream/icict/56995/2/Silva%2c%20L.P.%20Molecular%20Hybridization%20Strategy...2022.pdfb189a73a3fc66c040a9dc8f64991d31bMD52icict/569952023-03-15 14:32:52.049oai:www.arca.fiocruz.br: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ório InstitucionalPUBhttps://www.arca.fiocruz.br/oai/requestrepositorio.arca@fiocruz.bropendoar:21352023-03-15T17:32:52Repositório Institucional da FIOCRUZ (ARCA) - Fundação Oswaldo Cruz (FIOCRUZ)false |
| dc.title.en_US.fl_str_mv |
Molecular hybridization strategy on the design, synthesis, and structural characterization of ferrocene-n-acyl hydrazones as immunomodulatory agents |
| title |
Molecular hybridization strategy on the design, synthesis, and structural characterization of ferrocene-n-acyl hydrazones as immunomodulatory agents |
| spellingShingle |
Molecular hybridization strategy on the design, synthesis, and structural characterization of ferrocene-n-acyl hydrazones as immunomodulatory agents Silva, Laís Peres Immunomodulation Imunomodulação Choque endotóxico Peritonite aguda N-acil hidrazonas Ferroceno Immunomodulation Endotoxic shock Acute peritonitis N-acyl hydrazones ferrocene |
| title_short |
Molecular hybridization strategy on the design, synthesis, and structural characterization of ferrocene-n-acyl hydrazones as immunomodulatory agents |
| title_full |
Molecular hybridization strategy on the design, synthesis, and structural characterization of ferrocene-n-acyl hydrazones as immunomodulatory agents |
| title_fullStr |
Molecular hybridization strategy on the design, synthesis, and structural characterization of ferrocene-n-acyl hydrazones as immunomodulatory agents |
| title_full_unstemmed |
Molecular hybridization strategy on the design, synthesis, and structural characterization of ferrocene-n-acyl hydrazones as immunomodulatory agents |
| title_sort |
Molecular hybridization strategy on the design, synthesis, and structural characterization of ferrocene-n-acyl hydrazones as immunomodulatory agents |
| author |
Silva, Laís Peres |
| author_facet |
Silva, Laís Peres Santos, Ivanilson Pimenta Silva, Dahara Keyse Carvalho Reis, Bruna Padilha Zurita Claro dos Meira, Cássio Santana Castro, Marcos Venícius Batista de Souza Santos Filho, José Maurício dos Araujo Neto, João Honorato de Ellena, Javier Alcides Silveira, Rafael Gomes da Soares, Milena Botelho Pereira |
| author_role |
author |
| author2 |
Santos, Ivanilson Pimenta Silva, Dahara Keyse Carvalho Reis, Bruna Padilha Zurita Claro dos Meira, Cássio Santana Castro, Marcos Venícius Batista de Souza Santos Filho, José Maurício dos Araujo Neto, João Honorato de Ellena, Javier Alcides Silveira, Rafael Gomes da Soares, Milena Botelho Pereira |
| author2_role |
author author author author author author author author author author |
| dc.contributor.author.fl_str_mv |
Silva, Laís Peres Santos, Ivanilson Pimenta Silva, Dahara Keyse Carvalho Reis, Bruna Padilha Zurita Claro dos Meira, Cássio Santana Castro, Marcos Venícius Batista de Souza Santos Filho, José Maurício dos Araujo Neto, João Honorato de Ellena, Javier Alcides Silveira, Rafael Gomes da Soares, Milena Botelho Pereira |
| dc.subject.mesh.en_US.fl_str_mv |
Immunomodulation |
| topic |
Immunomodulation Imunomodulação Choque endotóxico Peritonite aguda N-acil hidrazonas Ferroceno Immunomodulation Endotoxic shock Acute peritonitis N-acyl hydrazones ferrocene |
| dc.subject.other.en_US.fl_str_mv |
Imunomodulação Choque endotóxico Peritonite aguda N-acil hidrazonas Ferroceno |
| dc.subject.en.en_US.fl_str_mv |
Immunomodulation Endotoxic shock Acute peritonitis N-acyl hydrazones ferrocene |
| description |
Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq). Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP). Programa de Apoio a Núcleos de Excelência (Pronex). |
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2022 |
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2022 |
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2023-02-09T19:43:50Z |
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2023-02-09T19:43:50Z |
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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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SILVA, Laís Peres et al. Molecular hybridization strategy on the design, synthesis, and structural characterization of ferrocene-n-acyl hydrazones as immunomodulatory agents. Molecules, v. 27, p. 1-22, 2022. |
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https://www.arca.fiocruz.br/handle/icict/56995 |
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1420-3049 |
| dc.identifier.doi.none.fl_str_mv |
10.3390/molecules27238343 |
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SILVA, Laís Peres et al. Molecular hybridization strategy on the design, synthesis, and structural characterization of ferrocene-n-acyl hydrazones as immunomodulatory agents. Molecules, v. 27, p. 1-22, 2022. 1420-3049 10.3390/molecules27238343 |
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MDPI |
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