Synthesis and structure-activity relationship study of a new series of antiparasitic aryloxyl thiosemicarbazones inhibiting Trypanosoma cruzi cruzain.

Espíndola, José Wanderlan Pontes; Cardoso, Marcos Veríssimo de Oliveira; Oliveira Filho, Gevanio Bezerra de; Silva, Dayane Albuquerque Oliveira e; Moreira, Diogo Rodrigo Magalhães; Bastos, Tanira Matutino; Simone, Carlos Alberto de; Soares, Milena Botelho Pereira; Villela, Filipe Silva; Ferreira, Rafaela Salgado; Castro, Maria Carolina Accioly Brelaz de; Pereira, Valeria Rego Alves; Murta, Silvane Maria Fonseca; Sales Junior, Policarpo Ademar; Romanha, Alvaro Jose; Leite, Ana Cristina Lima

Synthesis and structure-activity relationship study of a new series of antiparasitic aryloxyl thiosemicarbazones inhibiting Trypanosoma cruzi cruzain.

Bibliographic Details
Main Author:	Espíndola, José Wanderlan Pontes
Publication Date:	2015
Other Authors:	Cardoso, Marcos Veríssimo de Oliveira, Oliveira Filho, Gevanio Bezerra de, Silva, Dayane Albuquerque Oliveira e, Moreira, Diogo Rodrigo Magalhães, Bastos, Tanira Matutino, Simone, Carlos Alberto de, Soares, Milena Botelho Pereira, Villela, Filipe Silva, Ferreira, Rafaela Salgado, Castro, Maria Carolina Accioly Brelaz de, Pereira, Valeria Rego Alves, Murta, Silvane Maria Fonseca, Sales Junior, Policarpo Ademar, Romanha, Alvaro Jose, Leite, Ana Cristina Lima
Format:	Article
Language:	eng
Source:	Repositório Institucional da FIOCRUZ (ARCA)
Download full:	https://www.arca.fiocruz.br/handle/icict/13835
Summary:	Universidade Federal de Pernambuco. Centro de Ciências da Saúde. Departamento de Ciências Farmacêuticas. Recife, PE, Brasil

Item metadata

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network_acronym_str	CRUZ
network_name_str	Repositório Institucional da FIOCRUZ (ARCA)
repository_id_str	2135
spelling	Espíndola, José Wanderlan PontesCardoso, Marcos Veríssimo de OliveiraOliveira Filho, Gevanio Bezerra deSilva, Dayane Albuquerque Oliveira eMoreira, Diogo Rodrigo MagalhãesBastos, Tanira MatutinoSimone, Carlos Alberto deSoares, Milena Botelho PereiraVillela, Filipe SilvaFerreira, Rafaela SalgadoCastro, Maria Carolina Accioly Brelaz dePereira, Valeria Rego AlvesMurta, Silvane Maria FonsecaSales Junior, Policarpo AdemarRomanha, Alvaro JoseLeite, Ana Cristina Lima2016-04-15T18:24:38Z2016-04-15T18:24:38Z2015ESPINDOLA, J. W. P. et al. Synthesis and structure-activity relationship study of a new series of antiparasitic aryloxyl thiosemicarbazones inhibiting Trypanosoma cruzi cruzain. European Journal of Medicinal Chemistry, v. 101, p. 818-835, 2015.1768-3254https://www.arca.fiocruz.br/handle/icict/13835dx.doi.org/10.1016/j.ejmech.2015.06.048engElsevierSynthesis and structure-activity relationship study of a new series of antiparasitic aryloxyl thiosemicarbazones inhibiting Trypanosoma cruzi cruzain.info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleUniversidade Federal de Pernambuco. Centro de Ciências da Saúde. Departamento de Ciências Farmacêuticas. Recife, PE, BrasilUniversidade Federal de Pernambuco. Centro de Ciências da Saúde. Departamento de Ciências Farmacêuticas. Recife, PE, BrasilUniversidade Federal de Pernambuco. Centro de Ciências da Saúde. Departamento de Ciências Farmacêuticas. Recife, PE, BrasilUniversidade Federal de Pernambuco. Centro de Ciências da Saúde. Departamento de Ciências Farmacêuticas. Recife, PE, BrasilFundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, BrasilFundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, BrasilUniversidade de São Paulo. Instituto de Física. Departamento de Física e Inform atica. São Carlos, SP, BrasilFundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, Brasil / Hospital São Rafael. Centro de Biotecnologia e Terapia Celular. Salvador, BA, BrasilUniversidade Federal de Minas Gerais. Departamento de Bioquímica e Imunologia. Belo Horizonte, MG, BrasilUniversidade Federal de Minas Gerais. Departamento de Bioquímica e Imunologia. Belo Horizonte, MG, BrasilFundação Oswaldo Cruz. Centro de Pesquisas Aggeu Magalhães. Recife, PE, BrasiFundação Oswaldo Cruz. Centro de Pesquisas Aggeu Magalhães. Recife, PE, BrasiFundação Oswaldo Cruz. Centro de Pesquisas Ren e Rachou. Laborat ório de Parasitologia Celular e Molecular. Belo Horizonte, MG, BrasilFundação Oswaldo Cruz. Centro de Pesquisas Ren e Rachou. Laborat ório de Parasitologia Celular e Molecular. Belo Horizonte, MG, BrasilFundação Oswaldo Cruz. Centro de Pesquisas Ren e Rachou. Laborat ório de Parasitologia Celular e Molecular. Belo Horizonte, MG, BrasilUniversidade Federal de Pernambuco. Centro de Ciências da Saúde. Departamento de Ciências Farmacêuticas. Recife, PE, BrasilThe discovery of new antiparasitic compounds against Trypanosoma cruzi, the etiological agent of Chagas disease, is necessary. Novel aryloxy/aryl thiosemicarbazone-based conformationally constrained analogs of thiosemicarbazones (1) and (2) were developed as potential inhibitors of the T. cruzi protease cruzain, using a rigidification strategy of the iminic bond of (1) and (2). A structureeactivity relationship analysis was performed in substituents attached in both aryl and aryloxy rings. This study indicated that apolar substituents or halogen atom substitution at the aryl position improved cruzain inhibition and antiparasitic activity in comparison to unsubstituted thiosemicarbazone. Two of these compounds displayed potent inhibitory antiparasitic activity by inhibiting cruzain and consequently were able to reduce the parasite burden in infected cells and cause parasite cell death through necrosis. In conclusion, we demonstrated that conformational restriction is a valuable strategy in the development of antiparasitic thiosemicarbazones.Chagas diseaseTrypanosoma cruziConformationally constrained analogsThiosemicarbazoneCruzainNecrosisinfo: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/13835/1/license.txt5a560609d32a3863062d77ff32785d58MD51ORIGINALEspindola JWO Synthesis and structure....pdfEspindola JWO Synthesis and structure....pdfapplication/pdf2317914https://www.arca.fiocruz.br/bitstream/icict/13835/2/Espindola%20JWO%20Synthesis%20and%20structure....pdfbbb03141505669c2333311cba6a51a68MD52TEXTEspindola JWO Synthesis and structure....pdf.txtEspindola JWO Synthesis and structure....pdf.txtExtracted 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dc.title.pt_BR.fl_str_mv	Synthesis and structure-activity relationship study of a new series of antiparasitic aryloxyl thiosemicarbazones inhibiting Trypanosoma cruzi cruzain.
title	Synthesis and structure-activity relationship study of a new series of antiparasitic aryloxyl thiosemicarbazones inhibiting Trypanosoma cruzi cruzain.
spellingShingle	Synthesis and structure-activity relationship study of a new series of antiparasitic aryloxyl thiosemicarbazones inhibiting Trypanosoma cruzi cruzain. Espíndola, José Wanderlan Pontes Chagas disease Trypanosoma cruzi Conformationally constrained analogs Thiosemicarbazone Cruzain Necrosis
title_short	Synthesis and structure-activity relationship study of a new series of antiparasitic aryloxyl thiosemicarbazones inhibiting Trypanosoma cruzi cruzain.
title_full	Synthesis and structure-activity relationship study of a new series of antiparasitic aryloxyl thiosemicarbazones inhibiting Trypanosoma cruzi cruzain.
title_fullStr	Synthesis and structure-activity relationship study of a new series of antiparasitic aryloxyl thiosemicarbazones inhibiting Trypanosoma cruzi cruzain.
title_full_unstemmed	Synthesis and structure-activity relationship study of a new series of antiparasitic aryloxyl thiosemicarbazones inhibiting Trypanosoma cruzi cruzain.
title_sort	Synthesis and structure-activity relationship study of a new series of antiparasitic aryloxyl thiosemicarbazones inhibiting Trypanosoma cruzi cruzain.
author	Espíndola, José Wanderlan Pontes
author_facet	Espíndola, José Wanderlan Pontes Cardoso, Marcos Veríssimo de Oliveira Oliveira Filho, Gevanio Bezerra de Silva, Dayane Albuquerque Oliveira e Moreira, Diogo Rodrigo Magalhães Bastos, Tanira Matutino Simone, Carlos Alberto de Soares, Milena Botelho Pereira Villela, Filipe Silva Ferreira, Rafaela Salgado Castro, Maria Carolina Accioly Brelaz de Pereira, Valeria Rego Alves Murta, Silvane Maria Fonseca Sales Junior, Policarpo Ademar Romanha, Alvaro Jose Leite, Ana Cristina Lima
author_role	author
author2	Cardoso, Marcos Veríssimo de Oliveira Oliveira Filho, Gevanio Bezerra de Silva, Dayane Albuquerque Oliveira e Moreira, Diogo Rodrigo Magalhães Bastos, Tanira Matutino Simone, Carlos Alberto de Soares, Milena Botelho Pereira Villela, Filipe Silva Ferreira, Rafaela Salgado Castro, Maria Carolina Accioly Brelaz de Pereira, Valeria Rego Alves Murta, Silvane Maria Fonseca Sales Junior, Policarpo Ademar Romanha, Alvaro Jose Leite, Ana Cristina Lima
author2_role	author author author author author author author author author author author author author author author
dc.contributor.author.fl_str_mv	Espíndola, José Wanderlan Pontes Cardoso, Marcos Veríssimo de Oliveira Oliveira Filho, Gevanio Bezerra de Silva, Dayane Albuquerque Oliveira e Moreira, Diogo Rodrigo Magalhães Bastos, Tanira Matutino Simone, Carlos Alberto de Soares, Milena Botelho Pereira Villela, Filipe Silva Ferreira, Rafaela Salgado Castro, Maria Carolina Accioly Brelaz de Pereira, Valeria Rego Alves Murta, Silvane Maria Fonseca Sales Junior, Policarpo Ademar Romanha, Alvaro Jose Leite, Ana Cristina Lima
dc.subject.en.pt_BR.fl_str_mv	Chagas disease Trypanosoma cruzi Conformationally constrained analogs Thiosemicarbazone Cruzain Necrosis
topic	Chagas disease Trypanosoma cruzi Conformationally constrained analogs Thiosemicarbazone Cruzain Necrosis
description	Universidade Federal de Pernambuco. Centro de Ciências da Saúde. Departamento de Ciências Farmacêuticas. Recife, PE, Brasil
publishDate	2015
dc.date.issued.fl_str_mv	2015
dc.date.accessioned.fl_str_mv	2016-04-15T18:24:38Z
dc.date.available.fl_str_mv	2016-04-15T18:24:38Z
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	ESPINDOLA, J. W. P. et al. Synthesis and structure-activity relationship study of a new series of antiparasitic aryloxyl thiosemicarbazones inhibiting Trypanosoma cruzi cruzain. European Journal of Medicinal Chemistry, v. 101, p. 818-835, 2015.
dc.identifier.uri.fl_str_mv	https://www.arca.fiocruz.br/handle/icict/13835
dc.identifier.issn.none.fl_str_mv	1768-3254
dc.identifier.doi.none.fl_str_mv	dx.doi.org/10.1016/j.ejmech.2015.06.048
identifier_str_mv	ESPINDOLA, J. W. P. et al. Synthesis and structure-activity relationship study of a new series of antiparasitic aryloxyl thiosemicarbazones inhibiting Trypanosoma cruzi cruzain. European Journal of Medicinal Chemistry, v. 101, p. 818-835, 2015. 1768-3254 dx.doi.org/10.1016/j.ejmech.2015.06.048
url	https://www.arca.fiocruz.br/handle/icict/13835
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	Elsevier
publisher.none.fl_str_mv	Elsevier
dc.source.none.fl_str_mv	reponame:Repositório Institucional da FIOCRUZ (ARCA) instname:Fundação Oswaldo Cruz (FIOCRUZ) instacron:FIOCRUZ
instname_str	Fundação Oswaldo Cruz (FIOCRUZ)
instacron_str	FIOCRUZ
institution	FIOCRUZ
reponame_str	Repositório Institucional da FIOCRUZ (ARCA)
collection	Repositório Institucional da FIOCRUZ (ARCA)
bitstream.url.fl_str_mv	https://www.arca.fiocruz.br/bitstream/icict/13835/1/license.txt https://www.arca.fiocruz.br/bitstream/icict/13835/2/Espindola%20JWO%20Synthesis%20and%20structure....pdf https://www.arca.fiocruz.br/bitstream/icict/13835/3/Espindola%20JWO%20Synthesis%20and%20structure....pdf.txt
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repository.name.fl_str_mv	Repositório Institucional da FIOCRUZ (ARCA) - Fundação Oswaldo Cruz (FIOCRUZ)
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Synthesis and structure-activity relationship study of a new series of antiparasitic aryloxyl thiosemicarbazones inhibiting Trypanosoma cruzi cruzain.

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