Voltammetric behavior of nitrofurazone and its hydroxymethyl prodrug with potential anti-Chagas activity
Autor(a) principal: | |
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Data de Publicação: | 2005 |
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=S0103-50532005000500015 |
Resumo: | Chagas' disease is a serious health problem for Latin America. The situation is worsened by the lack of efficient chemotherapy. The two available commercial drugs, benznidazole and nifurtimox, are more effective in the acute phase of the disease. Nitrofurazone is active against Trypanosoma cruzi, however its high toxicity precludes its current use in parasitosis. Hydroxymethylnitrofurazone is a prodrug of nitrofurazone. It is more active against Trypanosoma cruzi than nitrofurazone, besides being less toxic. This work shows the voltammetric behavior of nitrofurazone and a comparison with those of metronidazole and chloramphenicol using cyclic, linear sweep and differential pulse voltammetries. For these drugs also the prediction of the diffusion coefficients using Wilke-Chang equation was performed. The reduction of nitrofurazone is pH-dependent and in acidic medium the hydroxylamine derivative, involving four electrons, is the principal product formed. In aqueous-alkaline medium and with a glassy carbon electrode pre-treatment the reduction of nitrofurazone occurs in two steps, the first involving one electron to form the nitro-radical anion and the second corresponding to the hydroxylamine derivative formation. Hydroxymethylnitrofurazone presented the same voltammetric behavior and electroactivity, indicating that the molecular modification performed in nitrofurazone did not change its capacity to be reduced. A brief discussion regarding the differences in biological activity between the two compounds is also presented. |
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Voltammetric behavior of nitrofurazone and its hydroxymethyl prodrug with potential anti-Chagas activitynitrofurazonehydroxymethylnitrofurazonenitrofurazone prodrugcyclic voltammetrynitro-radical anionChagas' disease is a serious health problem for Latin America. The situation is worsened by the lack of efficient chemotherapy. The two available commercial drugs, benznidazole and nifurtimox, are more effective in the acute phase of the disease. Nitrofurazone is active against Trypanosoma cruzi, however its high toxicity precludes its current use in parasitosis. Hydroxymethylnitrofurazone is a prodrug of nitrofurazone. It is more active against Trypanosoma cruzi than nitrofurazone, besides being less toxic. This work shows the voltammetric behavior of nitrofurazone and a comparison with those of metronidazole and chloramphenicol using cyclic, linear sweep and differential pulse voltammetries. For these drugs also the prediction of the diffusion coefficients using Wilke-Chang equation was performed. The reduction of nitrofurazone is pH-dependent and in acidic medium the hydroxylamine derivative, involving four electrons, is the principal product formed. In aqueous-alkaline medium and with a glassy carbon electrode pre-treatment the reduction of nitrofurazone occurs in two steps, the first involving one electron to form the nitro-radical anion and the second corresponding to the hydroxylamine derivative formation. Hydroxymethylnitrofurazone presented the same voltammetric behavior and electroactivity, indicating that the molecular modification performed in nitrofurazone did not change its capacity to be reduced. A brief discussion regarding the differences in biological activity between the two compounds is also presented.Sociedade Brasileira de Química2005-08-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532005000500015Journal of the Brazilian Chemical Society v.16 n.4 2005reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532005000500015info:eu-repo/semantics/openAccessLa-Scalea,Mauro AquilesMenezes,Carla Maria de SouzaJulião,Murilo Sérgio da SilvaChung,Man ChinSerrano,Sílvia Helena PiresFerreira,Elizabeth Igneeng2005-08-25T00:00:00Zoai:scielo:S0103-50532005000500015Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2005-08-25T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Voltammetric behavior of nitrofurazone and its hydroxymethyl prodrug with potential anti-Chagas activity |
title |
Voltammetric behavior of nitrofurazone and its hydroxymethyl prodrug with potential anti-Chagas activity |
spellingShingle |
Voltammetric behavior of nitrofurazone and its hydroxymethyl prodrug with potential anti-Chagas activity La-Scalea,Mauro Aquiles nitrofurazone hydroxymethylnitrofurazone nitrofurazone prodrug cyclic voltammetry nitro-radical anion |
title_short |
Voltammetric behavior of nitrofurazone and its hydroxymethyl prodrug with potential anti-Chagas activity |
title_full |
Voltammetric behavior of nitrofurazone and its hydroxymethyl prodrug with potential anti-Chagas activity |
title_fullStr |
Voltammetric behavior of nitrofurazone and its hydroxymethyl prodrug with potential anti-Chagas activity |
title_full_unstemmed |
Voltammetric behavior of nitrofurazone and its hydroxymethyl prodrug with potential anti-Chagas activity |
title_sort |
Voltammetric behavior of nitrofurazone and its hydroxymethyl prodrug with potential anti-Chagas activity |
author |
La-Scalea,Mauro Aquiles |
author_facet |
La-Scalea,Mauro Aquiles Menezes,Carla Maria de Souza Julião,Murilo Sérgio da Silva Chung,Man Chin Serrano,Sílvia Helena Pires Ferreira,Elizabeth Igne |
author_role |
author |
author2 |
Menezes,Carla Maria de Souza Julião,Murilo Sérgio da Silva Chung,Man Chin Serrano,Sílvia Helena Pires Ferreira,Elizabeth Igne |
author2_role |
author author author author author |
dc.contributor.author.fl_str_mv |
La-Scalea,Mauro Aquiles Menezes,Carla Maria de Souza Julião,Murilo Sérgio da Silva Chung,Man Chin Serrano,Sílvia Helena Pires Ferreira,Elizabeth Igne |
dc.subject.por.fl_str_mv |
nitrofurazone hydroxymethylnitrofurazone nitrofurazone prodrug cyclic voltammetry nitro-radical anion |
topic |
nitrofurazone hydroxymethylnitrofurazone nitrofurazone prodrug cyclic voltammetry nitro-radical anion |
description |
Chagas' disease is a serious health problem for Latin America. The situation is worsened by the lack of efficient chemotherapy. The two available commercial drugs, benznidazole and nifurtimox, are more effective in the acute phase of the disease. Nitrofurazone is active against Trypanosoma cruzi, however its high toxicity precludes its current use in parasitosis. Hydroxymethylnitrofurazone is a prodrug of nitrofurazone. It is more active against Trypanosoma cruzi than nitrofurazone, besides being less toxic. This work shows the voltammetric behavior of nitrofurazone and a comparison with those of metronidazole and chloramphenicol using cyclic, linear sweep and differential pulse voltammetries. For these drugs also the prediction of the diffusion coefficients using Wilke-Chang equation was performed. The reduction of nitrofurazone is pH-dependent and in acidic medium the hydroxylamine derivative, involving four electrons, is the principal product formed. In aqueous-alkaline medium and with a glassy carbon electrode pre-treatment the reduction of nitrofurazone occurs in two steps, the first involving one electron to form the nitro-radical anion and the second corresponding to the hydroxylamine derivative formation. Hydroxymethylnitrofurazone presented the same voltammetric behavior and electroactivity, indicating that the molecular modification performed in nitrofurazone did not change its capacity to be reduced. A brief discussion regarding the differences in biological activity between the two compounds is also presented. |
publishDate |
2005 |
dc.date.none.fl_str_mv |
2005-08-01 |
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=S0103-50532005000500015 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532005000500015 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.1590/S0103-50532005000500015 |
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.16 n.4 2005 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 |
_version_ |
1750318166532161536 |