Synthesis and evaluation of a pyrazinoic acid prodrug in Mycobacterium tuberculosis

Detalhes bibliográficos
Autor(a) principal: Fernandes, João Paulo dos Santos [UNIFESP]
Data de Publicação: 2014
Outros Autores: Pavan, Fernando Rogério, Leite, Clarice Queico Fujimura, Felli, Veni Maria Andres
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UNIFESP
Texto Completo: http://dx.doi.org/10.1016/j.jsps.2013.12.005
http://repositorio.unifesp.br/handle/11600/38118
Resumo: Tuberculosis (TB) is a disease caused mainly by infection of Mycobacterium tuberculosis affecting more than ten million people around the world. Despite TB can be treated, the rise of MDR-TB and XDR-TB cases put the disease in a worrying status. As pyrazinamide-resistant strains exhibit low or none pyrazinamidase activity, it is proposed that the active form of pyrazinamide (PZA) is pyrazinoic acid (POA), although this acid has poor penetration in mycobacteria. in this work, we present a convenient one-pot synthesis of 2-chloroethyl pyrazinoate, and its activity in M. tuberculosis H(37)Rv (ATCC27294) in MIC assay using the MABA technique. the obtained MIC of the compound was 3.96 g/mL, and discussion about the activity profile of some previously evaluated pyrazinoates is also performed. (C) 2013 King Saud University. Production and hosting by Elsevier B.V. All rights reserved.
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spelling Synthesis and evaluation of a pyrazinoic acid prodrug in Mycobacterium tuberculosisAntimycobacterial agentEster synthesisProdrugPyrazinoic acidTuberculostaticTuberculosis (TB) is a disease caused mainly by infection of Mycobacterium tuberculosis affecting more than ten million people around the world. Despite TB can be treated, the rise of MDR-TB and XDR-TB cases put the disease in a worrying status. As pyrazinamide-resistant strains exhibit low or none pyrazinamidase activity, it is proposed that the active form of pyrazinamide (PZA) is pyrazinoic acid (POA), although this acid has poor penetration in mycobacteria. in this work, we present a convenient one-pot synthesis of 2-chloroethyl pyrazinoate, and its activity in M. tuberculosis H(37)Rv (ATCC27294) in MIC assay using the MABA technique. the obtained MIC of the compound was 3.96 g/mL, and discussion about the activity profile of some previously evaluated pyrazinoates is also performed. (C) 2013 King Saud University. Production and hosting by Elsevier B.V. All rights reserved.Fed Univ São Paulo UNIFESP, Inst Environm Chem & Pharmaceut Sci, São Paulo, BrazilState Univ São Paulo UNESP, Fac Pharmaceut Sci, Dept Biol Sci, São Paulo, BrazilUniv São Paulo, Fac Pharmaceut Sci, Dept Pharm, BR-05508 São Paulo, BrazilFed Univ São Paulo UNIFESP, Inst Environm Chem & Pharmaceut Sci, São Paulo, BrazilWeb of ScienceFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)PROPEConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Elsevier B.V.Universidade Federal de São Paulo (UNIFESP)Universidade de São Paulo (USP)Fernandes, João Paulo dos Santos [UNIFESP]Pavan, Fernando RogérioLeite, Clarice Queico FujimuraFelli, Veni Maria Andres2016-01-24T14:37:45Z2016-01-24T14:37:45Z2014-09-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersion376-380application/pdfhttp://dx.doi.org/10.1016/j.jsps.2013.12.005Saudi Pharmaceutical Journal. Amsterdam: Elsevier B.V., v. 22, n. 4, p. 376-380, 2014.10.1016/j.jsps.2013.12.005WOS000341120900013.pdf1319-0164http://repositorio.unifesp.br/handle/11600/38118WOS:000341120900013engSaudi Pharmaceutical Journalinfo:eu-repo/semantics/openAccesshttp://www.elsevier.com/about/open-access/open-access-policies/article-posting-policyreponame:Repositório Institucional da UNIFESPinstname:Universidade Federal de São Paulo (UNIFESP)instacron:UNIFESP2024-08-08T16:51:43Zoai:repositorio.unifesp.br/:11600/38118Repositório InstitucionalPUBhttp://www.repositorio.unifesp.br/oai/requestbiblioteca.csp@unifesp.bropendoar:34652024-08-08T16:51:43Repositório Institucional da UNIFESP - Universidade Federal de São Paulo (UNIFESP)false
dc.title.none.fl_str_mv Synthesis and evaluation of a pyrazinoic acid prodrug in Mycobacterium tuberculosis
title Synthesis and evaluation of a pyrazinoic acid prodrug in Mycobacterium tuberculosis
spellingShingle Synthesis and evaluation of a pyrazinoic acid prodrug in Mycobacterium tuberculosis
Fernandes, João Paulo dos Santos [UNIFESP]
Antimycobacterial agent
Ester synthesis
Prodrug
Pyrazinoic acid
Tuberculostatic
title_short Synthesis and evaluation of a pyrazinoic acid prodrug in Mycobacterium tuberculosis
title_full Synthesis and evaluation of a pyrazinoic acid prodrug in Mycobacterium tuberculosis
title_fullStr Synthesis and evaluation of a pyrazinoic acid prodrug in Mycobacterium tuberculosis
title_full_unstemmed Synthesis and evaluation of a pyrazinoic acid prodrug in Mycobacterium tuberculosis
title_sort Synthesis and evaluation of a pyrazinoic acid prodrug in Mycobacterium tuberculosis
author Fernandes, João Paulo dos Santos [UNIFESP]
author_facet Fernandes, João Paulo dos Santos [UNIFESP]
Pavan, Fernando Rogério
Leite, Clarice Queico Fujimura
Felli, Veni Maria Andres
author_role author
author2 Pavan, Fernando Rogério
Leite, Clarice Queico Fujimura
Felli, Veni Maria Andres
author2_role author
author
author
dc.contributor.none.fl_str_mv Universidade Federal de São Paulo (UNIFESP)
Universidade de São Paulo (USP)
dc.contributor.author.fl_str_mv Fernandes, João Paulo dos Santos [UNIFESP]
Pavan, Fernando Rogério
Leite, Clarice Queico Fujimura
Felli, Veni Maria Andres
dc.subject.por.fl_str_mv Antimycobacterial agent
Ester synthesis
Prodrug
Pyrazinoic acid
Tuberculostatic
topic Antimycobacterial agent
Ester synthesis
Prodrug
Pyrazinoic acid
Tuberculostatic
description Tuberculosis (TB) is a disease caused mainly by infection of Mycobacterium tuberculosis affecting more than ten million people around the world. Despite TB can be treated, the rise of MDR-TB and XDR-TB cases put the disease in a worrying status. As pyrazinamide-resistant strains exhibit low or none pyrazinamidase activity, it is proposed that the active form of pyrazinamide (PZA) is pyrazinoic acid (POA), although this acid has poor penetration in mycobacteria. in this work, we present a convenient one-pot synthesis of 2-chloroethyl pyrazinoate, and its activity in M. tuberculosis H(37)Rv (ATCC27294) in MIC assay using the MABA technique. the obtained MIC of the compound was 3.96 g/mL, and discussion about the activity profile of some previously evaluated pyrazinoates is also performed. (C) 2013 King Saud University. Production and hosting by Elsevier B.V. All rights reserved.
publishDate 2014
dc.date.none.fl_str_mv 2014-09-01
2016-01-24T14:37:45Z
2016-01-24T14:37:45Z
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://dx.doi.org/10.1016/j.jsps.2013.12.005
Saudi Pharmaceutical Journal. Amsterdam: Elsevier B.V., v. 22, n. 4, p. 376-380, 2014.
10.1016/j.jsps.2013.12.005
WOS000341120900013.pdf
1319-0164
http://repositorio.unifesp.br/handle/11600/38118
WOS:000341120900013
url http://dx.doi.org/10.1016/j.jsps.2013.12.005
http://repositorio.unifesp.br/handle/11600/38118
identifier_str_mv Saudi Pharmaceutical Journal. Amsterdam: Elsevier B.V., v. 22, n. 4, p. 376-380, 2014.
10.1016/j.jsps.2013.12.005
WOS000341120900013.pdf
1319-0164
WOS:000341120900013
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Saudi Pharmaceutical Journal
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
http://www.elsevier.com/about/open-access/open-access-policies/article-posting-policy
eu_rights_str_mv openAccess
rights_invalid_str_mv http://www.elsevier.com/about/open-access/open-access-policies/article-posting-policy
dc.format.none.fl_str_mv 376-380
application/pdf
dc.publisher.none.fl_str_mv Elsevier B.V.
publisher.none.fl_str_mv Elsevier B.V.
dc.source.none.fl_str_mv reponame:Repositório Institucional da UNIFESP
instname:Universidade Federal de São Paulo (UNIFESP)
instacron:UNIFESP
instname_str Universidade Federal de São Paulo (UNIFESP)
instacron_str UNIFESP
institution UNIFESP
reponame_str Repositório Institucional da UNIFESP
collection Repositório Institucional da UNIFESP
repository.name.fl_str_mv Repositório Institucional da UNIFESP - Universidade Federal de São Paulo (UNIFESP)
repository.mail.fl_str_mv biblioteca.csp@unifesp.br
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