Synthesis and Anti-Chikungunya Virus (CHIKV) Activity of Novel 1,4-Naphthoquinone Sulfonamide and Sulfonate Ester Derivatives
Autor(a) principal: | |
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Data de Publicação: | 2022 |
Outros Autores: | , , , , , , , , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Journal of the Brazilian Chemical Society (Online) |
Texto Completo: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532022000600556 |
Resumo: | Chikungunya virus (CHIKV) is a re-emerging disease caused by an alphavirus of the Togaviridae family. Since its first description in 1952, the disease has spread worldwide, affecting populations in both tropical and temperate countries. To date, there is no licensed vaccine or specific pharmacological treatment. Therefore, there is an increasing urgency in developing new antiviral drugs capable of specifically inhibiting viral replication. In the present work, we report the synthesis and antiviral activity evaluation of nineteen naphthoquinone derivatives, containing a sulfonamide or sulfonate group. Cell viability assays indicated a low toxic potential for all tested compounds and inhibitory assays against CHIKV identified five compounds with potent activity. The compounds were also evaluated for their virucidal potential, and the results demonstrated that compound 11a exhibited a virucidal effect higher than 70% in the treatment with 20 µM. Furthermore, in silico studies were performed to predict the antiviral drug targets. |
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Synthesis and Anti-Chikungunya Virus (CHIKV) Activity of Novel 1,4-Naphthoquinone Sulfonamide and Sulfonate Ester DerivativesChikungunya virusnaphthoquinonesulfonamidesulfonateChikungunya virus (CHIKV) is a re-emerging disease caused by an alphavirus of the Togaviridae family. Since its first description in 1952, the disease has spread worldwide, affecting populations in both tropical and temperate countries. To date, there is no licensed vaccine or specific pharmacological treatment. Therefore, there is an increasing urgency in developing new antiviral drugs capable of specifically inhibiting viral replication. In the present work, we report the synthesis and antiviral activity evaluation of nineteen naphthoquinone derivatives, containing a sulfonamide or sulfonate group. Cell viability assays indicated a low toxic potential for all tested compounds and inhibitory assays against CHIKV identified five compounds with potent activity. The compounds were also evaluated for their virucidal potential, and the results demonstrated that compound 11a exhibited a virucidal effect higher than 70% in the treatment with 20 µM. Furthermore, in silico studies were performed to predict the antiviral drug targets.Sociedade Brasileira de Química2022-06-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532022000600556Journal of the Brazilian Chemical Society v.33 n.6 2022reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0103-5053.20220010info:eu-repo/semantics/openAccessPacheco,Paulo A. F.Gonzaga,Daniel T.Cirne-Santos,Cláudio C.Barros,Caroline S.Gomes,Max W. L.Gomes,Rafaela S. P.Gonçalves,Mariana C.Ferreira,Vitor F.Rabelo,Vitor W.Abreu,Paula A.Faria,Robson X.Resende,Gabriel O. deRocha,David R. daPaixão,Izabel C. N. P.Silva,Fernando C. daeng2022-05-27T00:00:00Zoai:scielo:S0103-50532022000600556Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2022-05-27T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Synthesis and Anti-Chikungunya Virus (CHIKV) Activity of Novel 1,4-Naphthoquinone Sulfonamide and Sulfonate Ester Derivatives |
title |
Synthesis and Anti-Chikungunya Virus (CHIKV) Activity of Novel 1,4-Naphthoquinone Sulfonamide and Sulfonate Ester Derivatives |
spellingShingle |
Synthesis and Anti-Chikungunya Virus (CHIKV) Activity of Novel 1,4-Naphthoquinone Sulfonamide and Sulfonate Ester Derivatives Pacheco,Paulo A. F. Chikungunya virus naphthoquinone sulfonamide sulfonate |
title_short |
Synthesis and Anti-Chikungunya Virus (CHIKV) Activity of Novel 1,4-Naphthoquinone Sulfonamide and Sulfonate Ester Derivatives |
title_full |
Synthesis and Anti-Chikungunya Virus (CHIKV) Activity of Novel 1,4-Naphthoquinone Sulfonamide and Sulfonate Ester Derivatives |
title_fullStr |
Synthesis and Anti-Chikungunya Virus (CHIKV) Activity of Novel 1,4-Naphthoquinone Sulfonamide and Sulfonate Ester Derivatives |
title_full_unstemmed |
Synthesis and Anti-Chikungunya Virus (CHIKV) Activity of Novel 1,4-Naphthoquinone Sulfonamide and Sulfonate Ester Derivatives |
title_sort |
Synthesis and Anti-Chikungunya Virus (CHIKV) Activity of Novel 1,4-Naphthoquinone Sulfonamide and Sulfonate Ester Derivatives |
author |
Pacheco,Paulo A. F. |
author_facet |
Pacheco,Paulo A. F. Gonzaga,Daniel T. Cirne-Santos,Cláudio C. Barros,Caroline S. Gomes,Max W. L. Gomes,Rafaela S. P. Gonçalves,Mariana C. Ferreira,Vitor F. Rabelo,Vitor W. Abreu,Paula A. Faria,Robson X. Resende,Gabriel O. de Rocha,David R. da Paixão,Izabel C. N. P. Silva,Fernando C. da |
author_role |
author |
author2 |
Gonzaga,Daniel T. Cirne-Santos,Cláudio C. Barros,Caroline S. Gomes,Max W. L. Gomes,Rafaela S. P. Gonçalves,Mariana C. Ferreira,Vitor F. Rabelo,Vitor W. Abreu,Paula A. Faria,Robson X. Resende,Gabriel O. de Rocha,David R. da Paixão,Izabel C. N. P. Silva,Fernando C. da |
author2_role |
author author author author author author author author author author author author author author |
dc.contributor.author.fl_str_mv |
Pacheco,Paulo A. F. Gonzaga,Daniel T. Cirne-Santos,Cláudio C. Barros,Caroline S. Gomes,Max W. L. Gomes,Rafaela S. P. Gonçalves,Mariana C. Ferreira,Vitor F. Rabelo,Vitor W. Abreu,Paula A. Faria,Robson X. Resende,Gabriel O. de Rocha,David R. da Paixão,Izabel C. N. P. Silva,Fernando C. da |
dc.subject.por.fl_str_mv |
Chikungunya virus naphthoquinone sulfonamide sulfonate |
topic |
Chikungunya virus naphthoquinone sulfonamide sulfonate |
description |
Chikungunya virus (CHIKV) is a re-emerging disease caused by an alphavirus of the Togaviridae family. Since its first description in 1952, the disease has spread worldwide, affecting populations in both tropical and temperate countries. To date, there is no licensed vaccine or specific pharmacological treatment. Therefore, there is an increasing urgency in developing new antiviral drugs capable of specifically inhibiting viral replication. In the present work, we report the synthesis and antiviral activity evaluation of nineteen naphthoquinone derivatives, containing a sulfonamide or sulfonate group. Cell viability assays indicated a low toxic potential for all tested compounds and inhibitory assays against CHIKV identified five compounds with potent activity. The compounds were also evaluated for their virucidal potential, and the results demonstrated that compound 11a exhibited a virucidal effect higher than 70% in the treatment with 20 µM. Furthermore, in silico studies were performed to predict the antiviral drug targets. |
publishDate |
2022 |
dc.date.none.fl_str_mv |
2022-06-01 |
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://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532022000600556 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532022000600556 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.21577/0103-5053.20220010 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
text/html |
dc.publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
dc.source.none.fl_str_mv |
Journal of the Brazilian Chemical Society v.33 n.6 2022 reponame:Journal of the Brazilian Chemical Society (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
instname_str |
Sociedade Brasileira de Química (SBQ) |
instacron_str |
SBQ |
institution |
SBQ |
reponame_str |
Journal of the Brazilian Chemical Society (Online) |
collection |
Journal of the Brazilian Chemical Society (Online) |
repository.name.fl_str_mv |
Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ) |
repository.mail.fl_str_mv |
||office@jbcs.sbq.org.br |
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1750318184861270016 |