The antimicrobial activity of lapachol and its thiosemicarbazone and semicarbazone derivatives
Lapachol was chemically modified to obtain its thiosemicarbazone and semicarbazone derivatives. These compounds were tested for antimicrobial activity against several bacteria and fungi by the broth microdilution method. The thiosemicarbazone and semicarbazone derivatives of lapachol exhibited antim...
| Main Authors: | , , , , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Fundação Oswaldo Cruz (FIOCRUZ)
2013-05-01
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| Series: | Memorias do Instituto Oswaldo Cruz |
| Subjects: | |
| Online Access: | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0074-02762013000300342&lng=en&tlng=en |
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| author | Marina Azevedo Souza Susana Johann Luciana Alves Rodrigues dos Santos Lima Fernanda Fraga Campos Isolda Castro Mendes Heloisa Beraldo Elaine Maria de Souza-Fagundes Patricia Silva Cisalpino Carlos Augusto Rosa Tania Maria de Almeida Alves Nivea Pereira de Sa Carlos Leomar Zani |
| author_facet | Marina Azevedo Souza Susana Johann Luciana Alves Rodrigues dos Santos Lima Fernanda Fraga Campos Isolda Castro Mendes Heloisa Beraldo Elaine Maria de Souza-Fagundes Patricia Silva Cisalpino Carlos Augusto Rosa Tania Maria de Almeida Alves Nivea Pereira de Sa Carlos Leomar Zani |
| author_sort | Marina Azevedo Souza |
| collection | DOAJ |
| description | Lapachol was chemically modified to obtain its thiosemicarbazone and semicarbazone derivatives. These compounds were tested for antimicrobial activity against several bacteria and fungi by the broth microdilution method. The thiosemicarbazone and semicarbazone derivatives of lapachol exhibited antimicrobial activity against the bacteria Enterococcus faecalis and Staphylococcus aureus with minimal inhibitory concentrations (MICs) of 0.05 and 0.10 µmol/mL, respectively. The thiosemicarbazone and semicarbazone derivatives were also active against the pathogenic yeast Cryptococcus gattii (MICs of 0.10 and 0.20 µmol/mL, respectively). In addition, the lapachol thiosemicarbazone derivative was active against 11 clinical isolates of Paracoccidioides brasiliensis, with MICs ranging from 0.01-0.10 µmol/mL. The lapachol-derived thiosemicarbazone was not cytotoxic to normal cells at the concentrations that were active against fungi and bacteria. We synthesised, for the first time, thiosemicarbazone and semicarbazone derivatives of lapachol. The MICs for the lapachol-derived thiosemicarbazone against S. aureus, E. faecalis, C. gattii and several isolates of P. brasiliensis indicated that this compound has the potential to be developed into novel drugs to treat infections caused these microbes. |
| first_indexed | 2024-03-12T05:01:24Z |
| format | Article |
| id | doaj.art-027217d590c14b23a841b40f6c2aebff |
| institution | Directory Open Access Journal |
| issn | 1678-8060 |
| language | English |
| last_indexed | 2024-03-12T05:01:24Z |
| publishDate | 2013-05-01 |
| publisher | Fundação Oswaldo Cruz (FIOCRUZ) |
| record_format | Article |
| series | Memorias do Instituto Oswaldo Cruz |
| spelling | doaj.art-027217d590c14b23a841b40f6c2aebff2023-09-03T09:11:43ZengFundação Oswaldo Cruz (FIOCRUZ)Memorias do Instituto Oswaldo Cruz1678-80602013-05-01108334235110.1590/S0074-02762013000300013S0074-02762013000300342The antimicrobial activity of lapachol and its thiosemicarbazone and semicarbazone derivativesMarina Azevedo SouzaSusana JohannLuciana Alves Rodrigues dos Santos LimaFernanda Fraga CamposIsolda Castro MendesHeloisa BeraldoElaine Maria de Souza-FagundesPatricia Silva CisalpinoCarlos Augusto RosaTania Maria de Almeida AlvesNivea Pereira de SaCarlos Leomar ZaniLapachol was chemically modified to obtain its thiosemicarbazone and semicarbazone derivatives. These compounds were tested for antimicrobial activity against several bacteria and fungi by the broth microdilution method. The thiosemicarbazone and semicarbazone derivatives of lapachol exhibited antimicrobial activity against the bacteria Enterococcus faecalis and Staphylococcus aureus with minimal inhibitory concentrations (MICs) of 0.05 and 0.10 µmol/mL, respectively. The thiosemicarbazone and semicarbazone derivatives were also active against the pathogenic yeast Cryptococcus gattii (MICs of 0.10 and 0.20 µmol/mL, respectively). In addition, the lapachol thiosemicarbazone derivative was active against 11 clinical isolates of Paracoccidioides brasiliensis, with MICs ranging from 0.01-0.10 µmol/mL. The lapachol-derived thiosemicarbazone was not cytotoxic to normal cells at the concentrations that were active against fungi and bacteria. We synthesised, for the first time, thiosemicarbazone and semicarbazone derivatives of lapachol. The MICs for the lapachol-derived thiosemicarbazone against S. aureus, E. faecalis, C. gattii and several isolates of P. brasiliensis indicated that this compound has the potential to be developed into novel drugs to treat infections caused these microbes.http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0074-02762013000300342&lng=en&tlng=enantimicrobial agentslapacholParacoccidioides |
| spellingShingle | Marina Azevedo Souza Susana Johann Luciana Alves Rodrigues dos Santos Lima Fernanda Fraga Campos Isolda Castro Mendes Heloisa Beraldo Elaine Maria de Souza-Fagundes Patricia Silva Cisalpino Carlos Augusto Rosa Tania Maria de Almeida Alves Nivea Pereira de Sa Carlos Leomar Zani The antimicrobial activity of lapachol and its thiosemicarbazone and semicarbazone derivatives Memorias do Instituto Oswaldo Cruz antimicrobial agents lapachol Paracoccidioides |
| title | The antimicrobial activity of lapachol and its thiosemicarbazone and semicarbazone derivatives |
| title_full | The antimicrobial activity of lapachol and its thiosemicarbazone and semicarbazone derivatives |
| title_fullStr | The antimicrobial activity of lapachol and its thiosemicarbazone and semicarbazone derivatives |
| title_full_unstemmed | The antimicrobial activity of lapachol and its thiosemicarbazone and semicarbazone derivatives |
| title_short | The antimicrobial activity of lapachol and its thiosemicarbazone and semicarbazone derivatives |
| title_sort | antimicrobial activity of lapachol and its thiosemicarbazone and semicarbazone derivatives |
| topic | antimicrobial agents lapachol Paracoccidioides |
| url | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0074-02762013000300342&lng=en&tlng=en |
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