Synthesis and Biological Evaluation of Novel 1,3-Benzoxathiol-2-one Sulfonamides against Toxic Activities of the Venom of Bothrops jararaca and Bothrops jararacussu Snakes

Detalhes bibliográficos
Autor(a) principal: Chazin,Eliza L.
Data de Publicação: 2022
Outros Autores: Martins,Leonardo B., Souza,Marcus Vinícius N. de, Gomes,Claudia Regina B., Silva,Ana Cláudia R. da, Branco,Marcelly C., Sanchez,Eladio F., Fuly,André L., Vasconcelos,Thatyana R. A.
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=S0103-50532022000100002
Resumo: This work describes the synthesis of new 1,3-benzoxathiol-2-one sulfonamides and evaluation of their ability to inhibit some in vitro (coagulant, proteolytic and hemolytic) and in vivo (hemorrhagic, edematogenic and lethality) toxic activities of Bothrops jararaca and Bothrops jararacussu venoms. Compounds have been synthesized from the coupling of intermediate 5-amino-6 methoxybenzo[d][1,3]oxathiol-2-one 4 with benzenesulfonyl chlorides. Characterization of the products was achieved by nuclear magnetic resonance (NMR) and electrospray ionization mass spectra (ESI-MS) techniques. Biological assay results have shown that most of compounds inhibited the main toxic activities of the venom of the two snake species. Compound 5b (N-(6 methoxy-2 oxobenzo[d][1,3]oxathiol-5-yl)-4-nitrobenzenesulfonamide) was the most efficient in inhibiting hemolysis of B. jararaca, and coagulation and proteolysis induced by both venoms. For in vivo activities, all compounds inhibited the edema, from 35 to 72%, and most of them exhibited antihemorrhagic and antilethality activities. Thus, the results pointed to the biological potential of these compounds, being promising molecules to treat envenomation by these snakes as well as to aid the current antivenom serum therapy.
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spelling Synthesis and Biological Evaluation of Novel 1,3-Benzoxathiol-2-one Sulfonamides against Toxic Activities of the Venom of Bothrops jararaca and Bothrops jararacussu Snakes1,3-benzoxathiol-2-onessulfonamidessnake venomBothrops jararacaBothrops jararacussuantivenomThis work describes the synthesis of new 1,3-benzoxathiol-2-one sulfonamides and evaluation of their ability to inhibit some in vitro (coagulant, proteolytic and hemolytic) and in vivo (hemorrhagic, edematogenic and lethality) toxic activities of Bothrops jararaca and Bothrops jararacussu venoms. Compounds have been synthesized from the coupling of intermediate 5-amino-6 methoxybenzo[d][1,3]oxathiol-2-one 4 with benzenesulfonyl chlorides. Characterization of the products was achieved by nuclear magnetic resonance (NMR) and electrospray ionization mass spectra (ESI-MS) techniques. Biological assay results have shown that most of compounds inhibited the main toxic activities of the venom of the two snake species. Compound 5b (N-(6 methoxy-2 oxobenzo[d][1,3]oxathiol-5-yl)-4-nitrobenzenesulfonamide) was the most efficient in inhibiting hemolysis of B. jararaca, and coagulation and proteolysis induced by both venoms. For in vivo activities, all compounds inhibited the edema, from 35 to 72%, and most of them exhibited antihemorrhagic and antilethality activities. Thus, the results pointed to the biological potential of these compounds, being promising molecules to treat envenomation by these snakes as well as to aid the current antivenom serum therapy.Sociedade Brasileira de Química2022-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532022000100002Journal of the Brazilian Chemical Society v.33 n.1 2022reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0103-5053.20210119info:eu-repo/semantics/openAccessChazin,Eliza L.Martins,Leonardo B.Souza,Marcus Vinícius N. deGomes,Claudia Regina B.Silva,Ana Cláudia R. daBranco,Marcelly C.Sanchez,Eladio F.Fuly,André L.Vasconcelos,Thatyana R. A.eng2022-01-06T00:00:00Zoai:scielo:S0103-50532022000100002Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2022-01-06T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Synthesis and Biological Evaluation of Novel 1,3-Benzoxathiol-2-one Sulfonamides against Toxic Activities of the Venom of Bothrops jararaca and Bothrops jararacussu Snakes
title Synthesis and Biological Evaluation of Novel 1,3-Benzoxathiol-2-one Sulfonamides against Toxic Activities of the Venom of Bothrops jararaca and Bothrops jararacussu Snakes
spellingShingle Synthesis and Biological Evaluation of Novel 1,3-Benzoxathiol-2-one Sulfonamides against Toxic Activities of the Venom of Bothrops jararaca and Bothrops jararacussu Snakes
Chazin,Eliza L.
1,3-benzoxathiol-2-ones
sulfonamides
snake venom
Bothrops jararaca
Bothrops jararacussu
antivenom
title_short Synthesis and Biological Evaluation of Novel 1,3-Benzoxathiol-2-one Sulfonamides against Toxic Activities of the Venom of Bothrops jararaca and Bothrops jararacussu Snakes
title_full Synthesis and Biological Evaluation of Novel 1,3-Benzoxathiol-2-one Sulfonamides against Toxic Activities of the Venom of Bothrops jararaca and Bothrops jararacussu Snakes
title_fullStr Synthesis and Biological Evaluation of Novel 1,3-Benzoxathiol-2-one Sulfonamides against Toxic Activities of the Venom of Bothrops jararaca and Bothrops jararacussu Snakes
title_full_unstemmed Synthesis and Biological Evaluation of Novel 1,3-Benzoxathiol-2-one Sulfonamides against Toxic Activities of the Venom of Bothrops jararaca and Bothrops jararacussu Snakes
title_sort Synthesis and Biological Evaluation of Novel 1,3-Benzoxathiol-2-one Sulfonamides against Toxic Activities of the Venom of Bothrops jararaca and Bothrops jararacussu Snakes
author Chazin,Eliza L.
author_facet Chazin,Eliza L.
Martins,Leonardo B.
Souza,Marcus Vinícius N. de
Gomes,Claudia Regina B.
Silva,Ana Cláudia R. da
Branco,Marcelly C.
Sanchez,Eladio F.
Fuly,André L.
Vasconcelos,Thatyana R. A.
author_role author
author2 Martins,Leonardo B.
Souza,Marcus Vinícius N. de
Gomes,Claudia Regina B.
Silva,Ana Cláudia R. da
Branco,Marcelly C.
Sanchez,Eladio F.
Fuly,André L.
Vasconcelos,Thatyana R. A.
author2_role author
author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Chazin,Eliza L.
Martins,Leonardo B.
Souza,Marcus Vinícius N. de
Gomes,Claudia Regina B.
Silva,Ana Cláudia R. da
Branco,Marcelly C.
Sanchez,Eladio F.
Fuly,André L.
Vasconcelos,Thatyana R. A.
dc.subject.por.fl_str_mv 1,3-benzoxathiol-2-ones
sulfonamides
snake venom
Bothrops jararaca
Bothrops jararacussu
antivenom
topic 1,3-benzoxathiol-2-ones
sulfonamides
snake venom
Bothrops jararaca
Bothrops jararacussu
antivenom
description This work describes the synthesis of new 1,3-benzoxathiol-2-one sulfonamides and evaluation of their ability to inhibit some in vitro (coagulant, proteolytic and hemolytic) and in vivo (hemorrhagic, edematogenic and lethality) toxic activities of Bothrops jararaca and Bothrops jararacussu venoms. Compounds have been synthesized from the coupling of intermediate 5-amino-6 methoxybenzo[d][1,3]oxathiol-2-one 4 with benzenesulfonyl chlorides. Characterization of the products was achieved by nuclear magnetic resonance (NMR) and electrospray ionization mass spectra (ESI-MS) techniques. Biological assay results have shown that most of compounds inhibited the main toxic activities of the venom of the two snake species. Compound 5b (N-(6 methoxy-2 oxobenzo[d][1,3]oxathiol-5-yl)-4-nitrobenzenesulfonamide) was the most efficient in inhibiting hemolysis of B. jararaca, and coagulation and proteolysis induced by both venoms. For in vivo activities, all compounds inhibited the edema, from 35 to 72%, and most of them exhibited antihemorrhagic and antilethality activities. Thus, the results pointed to the biological potential of these compounds, being promising molecules to treat envenomation by these snakes as well as to aid the current antivenom serum therapy.
publishDate 2022
dc.date.none.fl_str_mv 2022-01-01
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
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status_str publishedVersion
dc.identifier.uri.fl_str_mv http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532022000100002
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532022000100002
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.21577/0103-5053.20210119
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.1 2022
reponame:Journal of the Brazilian Chemical Society (Online)
instname:Sociedade Brasileira de Química (SBQ)
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instname_str Sociedade Brasileira de Química (SBQ)
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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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