Antimicrobial Effects of Silver(I) and Bismuth(III) Complexes with Secnidazole-Derived Schiff Base Ligands: the Role of the Nitro Group Reduction
Autor(a) principal: | |
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Data de Publicação: | 2019 |
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=S0103-50532019001102299 |
Resumo: | [Ag(HL)NO3] complexes (1-4) were obtained with (E)-N’-(1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ylidene)acetohydrazide (HL1); (E)-N’-(1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ylidene)benzohydrazide (HL2); (E)-2-(1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ylidene)hydrazinecarbothioamide (HL3) and (E)-N-methyl-2-(1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ylidene)hydrazinecarbothioamide (HL4) secnidazole-derived Schiff bases. In addition, complexes [Bi(HL3)Cl3] (5) and [Bi(HL4)Cl3] (6) were also prepared. The silver(I) complexes (1-4) showed antifungal activity against Candida fungal strains while the uncomplexed ligands and the bismuth(III) complexes (5-6) were inactive, suggesting that the antifungal effects are probably due to the presence of silver. Although the Schiff base ligands and complexes (1-6) revealed to be inactive against Gram-positive and Gram-negative aerobic bacteria, all compounds exhibited potent antimicrobial effects against several anaerobic bacterial strains, indicating that their mode of action probably involves anaerobic bio reduction of the nitro group, with formation of metabolites which are toxic to the microorganisms. Electrochemistry studies showed that bio reduction of the nitro group is favored in complexes (1-6) in comparison to the free ligands, which might, at least in part, explain their increased antimicrobial effects. |
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Antimicrobial Effects of Silver(I) and Bismuth(III) Complexes with Secnidazole-Derived Schiff Base Ligands: the Role of the Nitro Group Reductionsecnidazole Schiff basessilver(I) complexesbismuth(III) complexesantifungalantibacterialanaerobic bacteria[Ag(HL)NO3] complexes (1-4) were obtained with (E)-N’-(1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ylidene)acetohydrazide (HL1); (E)-N’-(1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ylidene)benzohydrazide (HL2); (E)-2-(1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ylidene)hydrazinecarbothioamide (HL3) and (E)-N-methyl-2-(1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ylidene)hydrazinecarbothioamide (HL4) secnidazole-derived Schiff bases. In addition, complexes [Bi(HL3)Cl3] (5) and [Bi(HL4)Cl3] (6) were also prepared. The silver(I) complexes (1-4) showed antifungal activity against Candida fungal strains while the uncomplexed ligands and the bismuth(III) complexes (5-6) were inactive, suggesting that the antifungal effects are probably due to the presence of silver. Although the Schiff base ligands and complexes (1-6) revealed to be inactive against Gram-positive and Gram-negative aerobic bacteria, all compounds exhibited potent antimicrobial effects against several anaerobic bacterial strains, indicating that their mode of action probably involves anaerobic bio reduction of the nitro group, with formation of metabolites which are toxic to the microorganisms. Electrochemistry studies showed that bio reduction of the nitro group is favored in complexes (1-6) in comparison to the free ligands, which might, at least in part, explain their increased antimicrobial effects.Sociedade Brasileira de Química2019-11-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532019001102299Journal of the Brazilian Chemical Society v.30 n.11 2019reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0103-5053.20190130info:eu-repo/semantics/openAccessOliveira,Ana P. A.Ferreira,João F. G.Farias,Luiz M.Magalhães,Paula P.Teixeira,Leticia R.Beraldo,Heloisaeng2019-10-18T00:00:00Zoai:scielo:S0103-50532019001102299Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2019-10-18T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Antimicrobial Effects of Silver(I) and Bismuth(III) Complexes with Secnidazole-Derived Schiff Base Ligands: the Role of the Nitro Group Reduction |
title |
Antimicrobial Effects of Silver(I) and Bismuth(III) Complexes with Secnidazole-Derived Schiff Base Ligands: the Role of the Nitro Group Reduction |
spellingShingle |
Antimicrobial Effects of Silver(I) and Bismuth(III) Complexes with Secnidazole-Derived Schiff Base Ligands: the Role of the Nitro Group Reduction Oliveira,Ana P. A. secnidazole Schiff bases silver(I) complexes bismuth(III) complexes antifungal antibacterial anaerobic bacteria |
title_short |
Antimicrobial Effects of Silver(I) and Bismuth(III) Complexes with Secnidazole-Derived Schiff Base Ligands: the Role of the Nitro Group Reduction |
title_full |
Antimicrobial Effects of Silver(I) and Bismuth(III) Complexes with Secnidazole-Derived Schiff Base Ligands: the Role of the Nitro Group Reduction |
title_fullStr |
Antimicrobial Effects of Silver(I) and Bismuth(III) Complexes with Secnidazole-Derived Schiff Base Ligands: the Role of the Nitro Group Reduction |
title_full_unstemmed |
Antimicrobial Effects of Silver(I) and Bismuth(III) Complexes with Secnidazole-Derived Schiff Base Ligands: the Role of the Nitro Group Reduction |
title_sort |
Antimicrobial Effects of Silver(I) and Bismuth(III) Complexes with Secnidazole-Derived Schiff Base Ligands: the Role of the Nitro Group Reduction |
author |
Oliveira,Ana P. A. |
author_facet |
Oliveira,Ana P. A. Ferreira,João F. G. Farias,Luiz M. Magalhães,Paula P. Teixeira,Leticia R. Beraldo,Heloisa |
author_role |
author |
author2 |
Ferreira,João F. G. Farias,Luiz M. Magalhães,Paula P. Teixeira,Leticia R. Beraldo,Heloisa |
author2_role |
author author author author author |
dc.contributor.author.fl_str_mv |
Oliveira,Ana P. A. Ferreira,João F. G. Farias,Luiz M. Magalhães,Paula P. Teixeira,Leticia R. Beraldo,Heloisa |
dc.subject.por.fl_str_mv |
secnidazole Schiff bases silver(I) complexes bismuth(III) complexes antifungal antibacterial anaerobic bacteria |
topic |
secnidazole Schiff bases silver(I) complexes bismuth(III) complexes antifungal antibacterial anaerobic bacteria |
description |
[Ag(HL)NO3] complexes (1-4) were obtained with (E)-N’-(1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ylidene)acetohydrazide (HL1); (E)-N’-(1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ylidene)benzohydrazide (HL2); (E)-2-(1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ylidene)hydrazinecarbothioamide (HL3) and (E)-N-methyl-2-(1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ylidene)hydrazinecarbothioamide (HL4) secnidazole-derived Schiff bases. In addition, complexes [Bi(HL3)Cl3] (5) and [Bi(HL4)Cl3] (6) were also prepared. The silver(I) complexes (1-4) showed antifungal activity against Candida fungal strains while the uncomplexed ligands and the bismuth(III) complexes (5-6) were inactive, suggesting that the antifungal effects are probably due to the presence of silver. Although the Schiff base ligands and complexes (1-6) revealed to be inactive against Gram-positive and Gram-negative aerobic bacteria, all compounds exhibited potent antimicrobial effects against several anaerobic bacterial strains, indicating that their mode of action probably involves anaerobic bio reduction of the nitro group, with formation of metabolites which are toxic to the microorganisms. Electrochemistry studies showed that bio reduction of the nitro group is favored in complexes (1-6) in comparison to the free ligands, which might, at least in part, explain their increased antimicrobial effects. |
publishDate |
2019 |
dc.date.none.fl_str_mv |
2019-11-01 |
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=S0103-50532019001102299 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532019001102299 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.21577/0103-5053.20190130 |
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.30 n.11 2019 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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1750318182195789824 |