Synthesis and evaluation of rifabutin analogs against Mycobacteium avium and H(37) Rv, MDR and NRP Mycobacterium tuberculosis
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2009 |
| 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/38828 |
Resumo: | 2020-12-26 |
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Figueiredo, RicardoMoiteiro, CristinaMedeiros, M. AugustaSilva, P. Almeida daRamos, D.Spies, F.Ribeiro, M. O.Lourenço, M. Cristina S.Neves Júnior, I. N.Gaspar, M. ManoelaCruz, M. Eugénia M.Curto, M. João MarceloFranzblau, S. G.Orozco, H.Aguilar, D.Hernandez-Pando, R.Costa, M. Céu2019-12-26T13:16:23Z2019-12-26T13:16:23Z2009FIGUEIREDO, Ricardo et al. Synthesis and evaluation of rifabutin analogs against Mycobacterium avium and H37Rv, MDR and NRPMycobacterium tuberculosis. Bioorganic and Medicinal Chemistry, v. 17, p. 503-511, 2009.0968-0896https://www.arca.fiocruz.br/handle/icict/3882810.1016/j.bmc.2008.12.006engElsevierSynthesis and evaluation of rifabutin analogs against Mycobacteium avium and H(37) Rv, MDR and NRP Mycobacterium tuberculosisinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article2020-12-26Instituto Nacional de Engenharia, Tecnologia e Inovação. Lisboa, Portugal.Instituto Nacional de Engenharia, Tecnologia e Inovação. Lisboa, Portugal.Instituto Nacional de Engenharia, Tecnologia e Inovação. Lisboa, Portugal.Universidade Federal do Rio Grande. Rio Grande, RS, Brasil.Universidade Federal do Rio Grande. Rio Grande, RS, Brasil.Universidade Federal do Rio Grande. Rio Grande, RS, Brasil.Universidade Federal do Rio Grande. Rio Grande, RS, Brasil.Fundação Oswaldo Cruz. Instituto Nacional de Infectologia Evandro Chagas. Rio de Janeiro, RJ, Brasil.Fundação Oswaldo Cruz. Instituto Nacional de Infectologia Evandro Chagas. Rio de Janeiro, RJ, Brasil.Instituto Nacional de Engenharia, Tecnologia e Inovação. Lisboa, Portugal.Instituto Nacional de Engenharia, Tecnologia e Inovação. Lisboa, Portugal.Instituto Nacional de Engenharia, Tecnologia e Inovação. Lisboa, Portugal..University of Illinois. Institute for Tuberculosis Research. Chicago, IL, USA.National Institute of Medical Sciences and Nutrition Salvador Zubirán. Mexico, DF, MexicoNational Institute of Medical Sciences and Nutrition Salvador Zubirán. Mexico, DF, MexicoNational Institute of Medical Sciences and Nutrition Salvador Zubirán. Mexico, DF, Mexico.Instituto Nacional de Engenharia, Tecnologia e Inovação. Lisboa, Portugal.Clinical utility of rifabutin1 (RBT), a potent antibiotic used in multidrug regimens for tuberculosis (TB) aswell as for infections caused by Mycobacterium avium complex (MAC), has been hampered due to dose-limiting toxicity. RBT analogs 2–11 were synthesized and evaluated against M. avium 1581 and Mycobacterium tuberculosis susceptible and resistant strains in vitro. A selection of candidates were also assayed against non-replicating persistent (NRP)M. tuberculosis. Subsequent in vivo studies with the best preclinical candidate drugs 5 and 8, in a model of progressive pulmonary tuberculosis of Balb/C mice infected either with H37Rv drug–sensible strain or with multidrug resistant (MDR) clinical isolates, resistant toall primary antibiotics including rifampicin, were performed. The results disclosed here suggest that 5 and 8 have potential for clinical application.TuberculosisMycobacterium aviumMycobacterium tuberculosisAnti-tuberculosis drugsinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da FIOCRUZ (ARCA)instname:Fundação Oswaldo Cruz (FIOCRUZ)instacron:FIOCRUZLICENSElicense.txttext/plain1748https://www.arca.fiocruz.br/bitstream/icict/38828/1/license.txt8a4605be74aa9ea9d79846c1fba20a33MD51ORIGINALve_Figueiredo_Ricardo_etal_INI_2009.pdfve_Figueiredo_Ricardo_etal_INI_2009.pdfapplication/pdf452535https://www.arca.fiocruz.br/bitstream/icict/38828/2/ve_Figueiredo_Ricardo_etal_INI_2009.pdf1f78d4f2132873e760fcfd70abdfc310MD52TEXTve_Figueiredo_Ricardo_etal_INI_2009.pdf.txtve_Figueiredo_Ricardo_etal_INI_2009.pdf.txtExtracted texttext/plain52588https://www.arca.fiocruz.br/bitstream/icict/38828/3/ve_Figueiredo_Ricardo_etal_INI_2009.pdf.txt9be8f0429cc60ca2e83da7704b39990eMD53icict/388282021-03-24 16:32:40.96oai:www.arca.fiocruz.br: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Repositório InstitucionalPUBhttps://www.arca.fiocruz.br/oai/requestrepositorio.arca@fiocruz.bropendoar:21352021-03-24T19:32:40Repositório Institucional da FIOCRUZ (ARCA) - Fundação Oswaldo Cruz (FIOCRUZ)false |
| dc.title.pt_BR.fl_str_mv |
Synthesis and evaluation of rifabutin analogs against Mycobacteium avium and H(37) Rv, MDR and NRP Mycobacterium tuberculosis |
| title |
Synthesis and evaluation of rifabutin analogs against Mycobacteium avium and H(37) Rv, MDR and NRP Mycobacterium tuberculosis |
| spellingShingle |
Synthesis and evaluation of rifabutin analogs against Mycobacteium avium and H(37) Rv, MDR and NRP Mycobacterium tuberculosis Figueiredo, Ricardo Tuberculosis Mycobacterium avium Mycobacterium tuberculosis Anti-tuberculosis drugs |
| title_short |
Synthesis and evaluation of rifabutin analogs against Mycobacteium avium and H(37) Rv, MDR and NRP Mycobacterium tuberculosis |
| title_full |
Synthesis and evaluation of rifabutin analogs against Mycobacteium avium and H(37) Rv, MDR and NRP Mycobacterium tuberculosis |
| title_fullStr |
Synthesis and evaluation of rifabutin analogs against Mycobacteium avium and H(37) Rv, MDR and NRP Mycobacterium tuberculosis |
| title_full_unstemmed |
Synthesis and evaluation of rifabutin analogs against Mycobacteium avium and H(37) Rv, MDR and NRP Mycobacterium tuberculosis |
| title_sort |
Synthesis and evaluation of rifabutin analogs against Mycobacteium avium and H(37) Rv, MDR and NRP Mycobacterium tuberculosis |
| author |
Figueiredo, Ricardo |
| author_facet |
Figueiredo, Ricardo Moiteiro, Cristina Medeiros, M. Augusta Silva, P. Almeida da Ramos, D. Spies, F. Ribeiro, M. O. Lourenço, M. Cristina S. Neves Júnior, I. N. Gaspar, M. Manoela Cruz, M. Eugénia M. Curto, M. João Marcelo Franzblau, S. G. Orozco, H. Aguilar, D. Hernandez-Pando, R. Costa, M. Céu |
| author_role |
author |
| author2 |
Moiteiro, Cristina Medeiros, M. Augusta Silva, P. Almeida da Ramos, D. Spies, F. Ribeiro, M. O. Lourenço, M. Cristina S. Neves Júnior, I. N. Gaspar, M. Manoela Cruz, M. Eugénia M. Curto, M. João Marcelo Franzblau, S. G. Orozco, H. Aguilar, D. Hernandez-Pando, R. Costa, M. Céu |
| author2_role |
author author author author author author author author author author author author author author author author |
| dc.contributor.author.fl_str_mv |
Figueiredo, Ricardo Moiteiro, Cristina Medeiros, M. Augusta Silva, P. Almeida da Ramos, D. Spies, F. Ribeiro, M. O. Lourenço, M. Cristina S. Neves Júnior, I. N. Gaspar, M. Manoela Cruz, M. Eugénia M. Curto, M. João Marcelo Franzblau, S. G. Orozco, H. Aguilar, D. Hernandez-Pando, R. Costa, M. Céu |
| dc.subject.en.pt_BR.fl_str_mv |
Tuberculosis Mycobacterium avium Mycobacterium tuberculosis Anti-tuberculosis drugs |
| topic |
Tuberculosis Mycobacterium avium Mycobacterium tuberculosis Anti-tuberculosis drugs |
| description |
2020-12-26 |
| publishDate |
2009 |
| dc.date.issued.fl_str_mv |
2009 |
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2019-12-26T13:16:23Z |
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2019-12-26T13:16:23Z |
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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 |
| dc.identifier.citation.fl_str_mv |
FIGUEIREDO, Ricardo et al. Synthesis and evaluation of rifabutin analogs against Mycobacterium avium and H37Rv, MDR and NRPMycobacterium tuberculosis. Bioorganic and Medicinal Chemistry, v. 17, p. 503-511, 2009. |
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https://www.arca.fiocruz.br/handle/icict/38828 |
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0968-0896 |
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10.1016/j.bmc.2008.12.006 |
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FIGUEIREDO, Ricardo et al. Synthesis and evaluation of rifabutin analogs against Mycobacterium avium and H37Rv, MDR and NRPMycobacterium tuberculosis. Bioorganic and Medicinal Chemistry, v. 17, p. 503-511, 2009. 0968-0896 10.1016/j.bmc.2008.12.006 |
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Elsevier |
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