Anti-Zika virus activity of several abietane-type ferruginol analogues
Autor(a) principal: | |
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Data de Publicação: | 2020 |
Outros Autores: | , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Revista do Instituto de Medicina Tropical de São Paulo |
Texto Completo: | https://www.revistas.usp.br/rimtsp/article/view/183599 |
Resumo: | Abietane diterpenoids are naturally occurring plant metabolites with a broad spectrum of biological effects including antibacterial, antileishmanial, antitumor, antioxidant, as well as antiinflammatory activities. Recently, we found that some analogues of natural ferruginol ( 2 ) actively inhibited dengue virus 2 (DENV-2) replication. Due to the similarity with DENV, we envisaged that abietane diterpenoids would also be active against Zika virus (ZIKV). Six selected semi-synthetic abietane derivatives of (+)-dehydroabietylamine ( 3 ) were tested. Cytotoxicity was determined by MTT assay in Vero cells. In vitro anti-ZIKV (clinical isolate, IMT17) activity was evaluated by plaque assay. Interestingly, these molecules showed potential as anti-ZIKV agents, with EC50 values ranging from 0.67 to 18.57 µM, and cytotoxicity (CC50 values) from 2.56 to 35.09 µM. The 18-Oxoferruginol (8) (EC50 = 2.60 µM, SI = 13.51) and 12-nitro-N-benzoyldehydroabietylamine (9) (EC50= 0.67 µM, SI = 3.82) were the most active compounds, followed by 12-hydroxy-N-tosyldehydroabietylamine ( 7 ) (EC50 = 3.58 µM, SI = 3.20) and 12-hydroxy-N,N-phthaloyldehydroabietylamine ( 5 ) (EC50 = 7.76 µM, SI = 1.23). To the best of our knowledge, this is the first report on anti-Zika virus properties of abietanes. |
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Anti-Zika virus activity of several abietane-type ferruginol analoguesZikaAbietaneDiterpenoidSemi-synthesisAnti-ZIKV activityAbietane diterpenoids are naturally occurring plant metabolites with a broad spectrum of biological effects including antibacterial, antileishmanial, antitumor, antioxidant, as well as antiinflammatory activities. Recently, we found that some analogues of natural ferruginol ( 2 ) actively inhibited dengue virus 2 (DENV-2) replication. Due to the similarity with DENV, we envisaged that abietane diterpenoids would also be active against Zika virus (ZIKV). Six selected semi-synthetic abietane derivatives of (+)-dehydroabietylamine ( 3 ) were tested. Cytotoxicity was determined by MTT assay in Vero cells. In vitro anti-ZIKV (clinical isolate, IMT17) activity was evaluated by plaque assay. Interestingly, these molecules showed potential as anti-ZIKV agents, with EC50 values ranging from 0.67 to 18.57 µM, and cytotoxicity (CC50 values) from 2.56 to 35.09 µM. The 18-Oxoferruginol (8) (EC50 = 2.60 µM, SI = 13.51) and 12-nitro-N-benzoyldehydroabietylamine (9) (EC50= 0.67 µM, SI = 3.82) were the most active compounds, followed by 12-hydroxy-N-tosyldehydroabietylamine ( 7 ) (EC50 = 3.58 µM, SI = 3.20) and 12-hydroxy-N,N-phthaloyldehydroabietylamine ( 5 ) (EC50 = 7.76 µM, SI = 1.23). To the best of our knowledge, this is the first report on anti-Zika virus properties of abietanes.Universidade de São Paulo. Instituto de Medicina Tropical de São Paulo2020-12-07info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttps://www.revistas.usp.br/rimtsp/article/view/18359910.1590/s1678-9946202062097 Revista do Instituto de Medicina Tropical de São Paulo; Vol. 62 (2020); e97Revista do Instituto de Medicina Tropical de São Paulo; Vol. 62 (2020); e97Revista do Instituto de Medicina Tropical de São Paulo; v. 62 (2020); e971678-99460036-4665reponame:Revista do Instituto de Medicina Tropical de São Pauloinstname:Instituto de Medicina Tropical (IMT)instacron:IMTenghttps://www.revistas.usp.br/rimtsp/article/view/183599/170145Copyright (c) 2021 Revista do Instituto de Medicina Tropical de São Paulohttp://creativecommons.org/licenses/by-nc/4.0info:eu-repo/semantics/openAccessSousa, Francielle T. G. Nunes, Cristina Romano, Camila Malta Sabino, Ester Cerdeira González-Cardenete, Miguel Angel 2021-03-25T20:30:30Zoai:revistas.usp.br:article/183599Revistahttp://www.revistas.usp.br/rimtsp/indexPUBhttps://www.revistas.usp.br/rimtsp/oai||revimtsp@usp.br1678-99460036-4665opendoar:2022-12-13T16:52:55.651860Revista do Instituto de Medicina Tropical de São Paulo - Instituto de Medicina Tropical (IMT)true |
dc.title.none.fl_str_mv |
Anti-Zika virus activity of several abietane-type ferruginol analogues |
title |
Anti-Zika virus activity of several abietane-type ferruginol analogues |
spellingShingle |
Anti-Zika virus activity of several abietane-type ferruginol analogues Sousa, Francielle T. G. Zika Abietane Diterpenoid Semi-synthesis Anti-ZIKV activity |
title_short |
Anti-Zika virus activity of several abietane-type ferruginol analogues |
title_full |
Anti-Zika virus activity of several abietane-type ferruginol analogues |
title_fullStr |
Anti-Zika virus activity of several abietane-type ferruginol analogues |
title_full_unstemmed |
Anti-Zika virus activity of several abietane-type ferruginol analogues |
title_sort |
Anti-Zika virus activity of several abietane-type ferruginol analogues |
author |
Sousa, Francielle T. G. |
author_facet |
Sousa, Francielle T. G. Nunes, Cristina Romano, Camila Malta Sabino, Ester Cerdeira González-Cardenete, Miguel Angel |
author_role |
author |
author2 |
Nunes, Cristina Romano, Camila Malta Sabino, Ester Cerdeira González-Cardenete, Miguel Angel |
author2_role |
author author author author |
dc.contributor.author.fl_str_mv |
Sousa, Francielle T. G. Nunes, Cristina Romano, Camila Malta Sabino, Ester Cerdeira González-Cardenete, Miguel Angel |
dc.subject.por.fl_str_mv |
Zika Abietane Diterpenoid Semi-synthesis Anti-ZIKV activity |
topic |
Zika Abietane Diterpenoid Semi-synthesis Anti-ZIKV activity |
description |
Abietane diterpenoids are naturally occurring plant metabolites with a broad spectrum of biological effects including antibacterial, antileishmanial, antitumor, antioxidant, as well as antiinflammatory activities. Recently, we found that some analogues of natural ferruginol ( 2 ) actively inhibited dengue virus 2 (DENV-2) replication. Due to the similarity with DENV, we envisaged that abietane diterpenoids would also be active against Zika virus (ZIKV). Six selected semi-synthetic abietane derivatives of (+)-dehydroabietylamine ( 3 ) were tested. Cytotoxicity was determined by MTT assay in Vero cells. In vitro anti-ZIKV (clinical isolate, IMT17) activity was evaluated by plaque assay. Interestingly, these molecules showed potential as anti-ZIKV agents, with EC50 values ranging from 0.67 to 18.57 µM, and cytotoxicity (CC50 values) from 2.56 to 35.09 µM. The 18-Oxoferruginol (8) (EC50 = 2.60 µM, SI = 13.51) and 12-nitro-N-benzoyldehydroabietylamine (9) (EC50= 0.67 µM, SI = 3.82) were the most active compounds, followed by 12-hydroxy-N-tosyldehydroabietylamine ( 7 ) (EC50 = 3.58 µM, SI = 3.20) and 12-hydroxy-N,N-phthaloyldehydroabietylamine ( 5 ) (EC50 = 7.76 µM, SI = 1.23). To the best of our knowledge, this is the first report on anti-Zika virus properties of abietanes. |
publishDate |
2020 |
dc.date.none.fl_str_mv |
2020-12-07 |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
https://www.revistas.usp.br/rimtsp/article/view/183599 10.1590/s1678-9946202062097 |
url |
https://www.revistas.usp.br/rimtsp/article/view/183599 |
identifier_str_mv |
10.1590/s1678-9946202062097 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
https://www.revistas.usp.br/rimtsp/article/view/183599/170145 |
dc.rights.driver.fl_str_mv |
Copyright (c) 2021 Revista do Instituto de Medicina Tropical de São Paulo http://creativecommons.org/licenses/by-nc/4.0 info:eu-repo/semantics/openAccess |
rights_invalid_str_mv |
Copyright (c) 2021 Revista do Instituto de Medicina Tropical de São Paulo http://creativecommons.org/licenses/by-nc/4.0 |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
Universidade de São Paulo. Instituto de Medicina Tropical de São Paulo |
publisher.none.fl_str_mv |
Universidade de São Paulo. Instituto de Medicina Tropical de São Paulo |
dc.source.none.fl_str_mv |
Revista do Instituto de Medicina Tropical de São Paulo; Vol. 62 (2020); e97 Revista do Instituto de Medicina Tropical de São Paulo; Vol. 62 (2020); e97 Revista do Instituto de Medicina Tropical de São Paulo; v. 62 (2020); e97 1678-9946 0036-4665 reponame:Revista do Instituto de Medicina Tropical de São Paulo instname:Instituto de Medicina Tropical (IMT) instacron:IMT |
instname_str |
Instituto de Medicina Tropical (IMT) |
instacron_str |
IMT |
institution |
IMT |
reponame_str |
Revista do Instituto de Medicina Tropical de São Paulo |
collection |
Revista do Instituto de Medicina Tropical de São Paulo |
repository.name.fl_str_mv |
Revista do Instituto de Medicina Tropical de São Paulo - Instituto de Medicina Tropical (IMT) |
repository.mail.fl_str_mv |
||revimtsp@usp.br |
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1798951653097865216 |