Docking, synthesis and antiproliferative activity of N-acylhydrazone derivatives designed as combretastatin A4 analogues
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2014 |
| 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/20893 |
Resumo: | Bezerra, Daniel Pereira “Documento produzido em parceria ou por autor vinculado à Fiocruz, mas não consta à informação no documento”. |
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Amaral, Daniel Nascimento doCavalcanti, Bruno CoelhoBezerra, Daniel PereiraFerreira, Paulo Michel PinheiroCastro, Rosane de PaulaSabino, José RicardoMachado, Camila Maria LongoChammas, RogerPessoa, ClaudiaSant'Anna, Carlos Mauricio Rabello deBarreiro, Eliezer Jesus de LacerdaLima, Lídia Moreira2017-09-01T16:48:48Z2017-09-01T16:48:48Z2014AMARAL, D. N. et al. Docking, synthesis and antiproliferative activity of N-acylhydrazone derivatives designed as combretastatin A4 analogues. Plos One, v. 9, n. 3, p. e85380, 2014.1932-6203https://www.arca.fiocruz.br/handle/icict/2089310.1371/journal.pone.0085380Bezerra, Daniel Pereira “Documento produzido em parceria ou por autor vinculado à Fiocruz, mas não consta à informação no documento”.CNPq (BR), FAPERJ (BR) and INCT-INOFAR (BR, 573.564/2008-6 and E-26/170.020/2008).Universidade Federal do Rio de Janeiro. Instituto Nacional de Ciência e Tecnologia de Fármacos e Medicamentos. Laboratório de Avaliação e Síntese de Substâncias Bioativas. Rio de Janeiro, RJ, Brasil / Universidade Federal do Rio de Janeiro. Instituto de Qu[imica. Programa de Pós-Graduação em Química. Rio de Janeiro, RJ, BrasilUniversidade Federal do Ceará. Faculdade de Medicina. Departamento de Fisiologia e Farmacologia. Fortaleza, CE, BrasilUniversidade Federal do Ceará. Faculdade de Medicina. Departamento de Fisiologia e Farmacologia. Fortaleza, CE, BrasilUniversidade Federal do Piauí. Departamento de Ciências Biológicas. Picos, PI, BrasilUniversidade Federal de Goiás. Instituto de Fısica. Goiânia, GO, BrasilUniversidade Federal de Goiás. Instituto de Fısica. Goiânia, GO, BrasilUniversidade de São Paulo. Faculdade de Medicina. Departamento de Radiologia. São Paulo, SP, BrasilUniversidade de São Paulo. Faculdade de Medicina. Departamento de Radiologia. São Paulo, SP, BrasilUniversidade Federal do Ceará. Faculdade de Medicina. Departamento de Fisiologia e Farmacologia. Fortaleza, CE, BrasilUniversidade Federal Rural do Rio de Janeiro. Departamento de Química. Seropédica, RJ, BrasilUniversidade Federal do Rio de Janeiro. Instituto Nacional de Ciência e Tecnologia de Fármacos e Medicamentos. Laboratório de Avaliação e Síntese de Substâncias Bioativas. Rio de Janeiro, RJ, Brasil / Universidade Federal do Rio de Janeiro. Instituto de Qu[imica. Programa de Pós-Graduação em Química. Rio de Janeiro, RJ, BrasilUniversidade Federal do Rio de Janeiro. Instituto Nacional de Ciência e Tecnologia de Fármacos e Medicamentos. Laboratório de Avaliação e Síntese de Substâncias Bioativas. Rio de Janeiro, RJ, Brasil / Universidade Federal do Rio de Janeiro. Instituto de Qu[imica. Programa de Pós-Graduação em Química. Rio de Janeiro, RJ, BrasilCancer is the second most common cause of death in the USA. Among the known classes of anticancer agents, the microtubule-targeted antimitotic drugs are considered to be one of the most important. They are usually classified into microtubule-destabilizing (e.g., Vinca alkaloids) and microtubule-stabilizing (e.g., paclitaxel) agents. Combretastatin A4 (CA-4), which is a natural stilbene isolated from Combretum caffrum, is a microtubule-destabilizing agent that binds to the colchicine domain on β-tubulin and exhibits a lower toxicity profile than paclitaxel or the Vinca alkaloids. In this paper, we describe the docking study, synthesis, antiproliferative activity and selectivity index of the N-acylhydrazone derivatives (5a-r) designed as CA-4 analogues. The essential structural requirements for molecular recognition by the colchicine binding site of β-tubulin were recognized, and several compounds with moderate to high antiproliferative potency (IC50 values ≤18 µM and ≥4 nM) were identified. Among these active compounds, LASSBio-1586 (5b) emerged as a simple antitumor drug candidate, which is capable of inhibiting microtubule polymerization and possesses a broad in vitro and in vivo antiproliferative profile, as well as a better selectivity index than the prototype CA-4, indicating improved selective cytotoxicity toward cancer cells.engPublic Library of ScienceTumorProliferação celularColchicinaMicrotúbulosAgentes antineoplásicosMolecular Docking SimulationCell Line, TumorCell ProliferationColchicineMicrotubulesAntineoplastic AgentsDocking, synthesis and antiproliferative activity of N-acylhydrazone derivatives designed as combretastatin A4 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/20893/1/license.txt5a560609d32a3863062d77ff32785d58MD51ORIGINALAmaral DN Docking, synthesis....pdfAmaral DN Docking, synthesis....pdfapplication/pdf7100112https://www.arca.fiocruz.br/bitstream/icict/20893/2/Amaral%20DN%20Docking%2c%20synthesis....pdf693f90bf2881284d5f3e48f5b4c376feMD52TEXTAmaral DN Docking, synthesis....pdf.txtAmaral DN Docking, synthesis....pdf.txtExtracted texttext/plain75761https://www.arca.fiocruz.br/bitstream/icict/20893/3/Amaral%20DN%20Docking%2c%20synthesis....pdf.txt22c432ac639ab1d24c544fab93432e45MD53icict/208932023-03-15 14:33:53.494oai:www.arca.fiocruz.br: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ório 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| dc.title.pt_BR.fl_str_mv |
Docking, synthesis and antiproliferative activity of N-acylhydrazone derivatives designed as combretastatin A4 analogues |
| title |
Docking, synthesis and antiproliferative activity of N-acylhydrazone derivatives designed as combretastatin A4 analogues |
| spellingShingle |
Docking, synthesis and antiproliferative activity of N-acylhydrazone derivatives designed as combretastatin A4 analogues Amaral, Daniel Nascimento do Tumor Proliferação celular Colchicina Microtúbulos Agentes antineoplásicos Molecular Docking Simulation Cell Line, Tumor Cell Proliferation Colchicine Microtubules Antineoplastic Agents |
| title_short |
Docking, synthesis and antiproliferative activity of N-acylhydrazone derivatives designed as combretastatin A4 analogues |
| title_full |
Docking, synthesis and antiproliferative activity of N-acylhydrazone derivatives designed as combretastatin A4 analogues |
| title_fullStr |
Docking, synthesis and antiproliferative activity of N-acylhydrazone derivatives designed as combretastatin A4 analogues |
| title_full_unstemmed |
Docking, synthesis and antiproliferative activity of N-acylhydrazone derivatives designed as combretastatin A4 analogues |
| title_sort |
Docking, synthesis and antiproliferative activity of N-acylhydrazone derivatives designed as combretastatin A4 analogues |
| author |
Amaral, Daniel Nascimento do |
| author_facet |
Amaral, Daniel Nascimento do Cavalcanti, Bruno Coelho Bezerra, Daniel Pereira Ferreira, Paulo Michel Pinheiro Castro, Rosane de Paula Sabino, José Ricardo Machado, Camila Maria Longo Chammas, Roger Pessoa, Claudia Sant'Anna, Carlos Mauricio Rabello de Barreiro, Eliezer Jesus de Lacerda Lima, Lídia Moreira |
| author_role |
author |
| author2 |
Cavalcanti, Bruno Coelho Bezerra, Daniel Pereira Ferreira, Paulo Michel Pinheiro Castro, Rosane de Paula Sabino, José Ricardo Machado, Camila Maria Longo Chammas, Roger Pessoa, Claudia Sant'Anna, Carlos Mauricio Rabello de Barreiro, Eliezer Jesus de Lacerda Lima, Lídia Moreira |
| author2_role |
author author author author author author author author author author author |
| dc.contributor.author.fl_str_mv |
Amaral, Daniel Nascimento do Cavalcanti, Bruno Coelho Bezerra, Daniel Pereira Ferreira, Paulo Michel Pinheiro Castro, Rosane de Paula Sabino, José Ricardo Machado, Camila Maria Longo Chammas, Roger Pessoa, Claudia Sant'Anna, Carlos Mauricio Rabello de Barreiro, Eliezer Jesus de Lacerda Lima, Lídia Moreira |
| dc.subject.other.pt_BR.fl_str_mv |
Tumor Proliferação celular Colchicina Microtúbulos Agentes antineoplásicos |
| topic |
Tumor Proliferação celular Colchicina Microtúbulos Agentes antineoplásicos Molecular Docking Simulation Cell Line, Tumor Cell Proliferation Colchicine Microtubules Antineoplastic Agents |
| dc.subject.en.pt_BR.fl_str_mv |
Molecular Docking Simulation Cell Line, Tumor Cell Proliferation Colchicine Microtubules Antineoplastic Agents |
| description |
Bezerra, Daniel Pereira “Documento produzido em parceria ou por autor vinculado à Fiocruz, mas não consta à informação no documento”. |
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2014 |
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2014 |
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2017-09-01T16:48:48Z |
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2017-09-01T16:48:48Z |
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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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AMARAL, D. N. et al. Docking, synthesis and antiproliferative activity of N-acylhydrazone derivatives designed as combretastatin A4 analogues. Plos One, v. 9, n. 3, p. e85380, 2014. |
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https://www.arca.fiocruz.br/handle/icict/20893 |
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1932-6203 |
| dc.identifier.doi.none.fl_str_mv |
10.1371/journal.pone.0085380 |
| identifier_str_mv |
AMARAL, D. N. et al. Docking, synthesis and antiproliferative activity of N-acylhydrazone derivatives designed as combretastatin A4 analogues. Plos One, v. 9, n. 3, p. e85380, 2014. 1932-6203 10.1371/journal.pone.0085380 |
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Public Library of Science |
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