Synthesis and Anti-Chikungunya Virus (CHIKV) Activity of Novel 1,4-Naphthoquinone Sulfonamide and Sulfonate Ester Derivatives

Detalhes bibliográficos
Autor(a) principal: Pacheco,Paulo A. F.
Data de Publicação: 2022
Outros Autores: 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
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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spelling 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)
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