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: | , , , , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Fundação Oswaldo Cruz (FIOCRUZ)
2013-05-01
|
| Series: | Memorias do Instituto Oswaldo Cruz |
| Subjects: | |
| Online Access: | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0074-02762013000300342 |
| _version_ | 1827879865420873728 |
|---|---|
| author | Marina Azevêdo Souza Susana Johann Luciana Alves Rodrigues dos Santos Lima Fernanda Fraga Campos Isolda Castro Mendes Heloisa Beraldo Elaine Maria de Souza-Fagundes Patrícia Silva Cisalpino Carlos Augusto Rosa Tânia Maria de Almeida Alves Nívea Pereira de Sá Carlos Leomar Zani |
| author_facet | Marina Azevêdo Souza Susana Johann Luciana Alves Rodrigues dos Santos Lima Fernanda Fraga Campos Isolda Castro Mendes Heloisa Beraldo Elaine Maria de Souza-Fagundes Patrícia Silva Cisalpino Carlos Augusto Rosa Tânia Maria de Almeida Alves Nívea Pereira de Sá Carlos Leomar Zani |
| author_sort | Marina Azevêdo 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 | 2024-03-12T18:12:26Z |
| format | Article |
| id | doaj.art-8049d78a4fa546afb46f5a4cd64d77f8 |
| institution | Directory Open Access Journal |
| issn | 0074-0276 1678-8060 |
| language | English |
| last_indexed | 2024-03-12T18:12:26Z |
| publishDate | 2013-05-01 |
| publisher | Fundação Oswaldo Cruz (FIOCRUZ) |
| record_format | Article |
| series | Memorias do Instituto Oswaldo Cruz |
| spelling | doaj.art-8049d78a4fa546afb46f5a4cd64d77f82023-08-02T09:15:10ZengFundação Oswaldo Cruz (FIOCRUZ)Memorias do Instituto Oswaldo Cruz0074-02761678-80602013-05-011083342351The antimicrobial activity of lapachol and its thiosemicarbazone and semicarbazone derivativesMarina Azevêdo SouzaSusana JohannLuciana Alves Rodrigues dos Santos LimaFernanda Fraga CamposIsolda Castro MendesHeloisa BeraldoElaine Maria de Souza-FagundesPatrícia Silva CisalpinoCarlos Augusto RosaTânia Maria de Almeida AlvesNívea Pereira de SáCarlos 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=S0074-02762013000300342antimicrobial agentslapacholParacoccidioides |
| spellingShingle | Marina Azevêdo Souza Susana Johann Luciana Alves Rodrigues dos Santos Lima Fernanda Fraga Campos Isolda Castro Mendes Heloisa Beraldo Elaine Maria de Souza-Fagundes Patrícia Silva Cisalpino Carlos Augusto Rosa Tânia Maria de Almeida Alves Nívea Pereira de Sá 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 |
| work_keys_str_mv | AT marinaazevedosouza theantimicrobialactivityoflapacholanditsthiosemicarbazoneandsemicarbazonederivatives AT susanajohann theantimicrobialactivityoflapacholanditsthiosemicarbazoneandsemicarbazonederivatives AT lucianaalvesrodriguesdossantoslima theantimicrobialactivityoflapacholanditsthiosemicarbazoneandsemicarbazonederivatives AT fernandafragacampos theantimicrobialactivityoflapacholanditsthiosemicarbazoneandsemicarbazonederivatives AT isoldacastromendes theantimicrobialactivityoflapacholanditsthiosemicarbazoneandsemicarbazonederivatives AT heloisaberaldo theantimicrobialactivityoflapacholanditsthiosemicarbazoneandsemicarbazonederivatives AT elainemariadesouzafagundes theantimicrobialactivityoflapacholanditsthiosemicarbazoneandsemicarbazonederivatives AT patriciasilvacisalpino theantimicrobialactivityoflapacholanditsthiosemicarbazoneandsemicarbazonederivatives AT carlosaugustorosa theantimicrobialactivityoflapacholanditsthiosemicarbazoneandsemicarbazonederivatives AT taniamariadealmeidaalves theantimicrobialactivityoflapacholanditsthiosemicarbazoneandsemicarbazonederivatives AT niveapereiradesa theantimicrobialactivityoflapacholanditsthiosemicarbazoneandsemicarbazonederivatives AT carlosleomarzani theantimicrobialactivityoflapacholanditsthiosemicarbazoneandsemicarbazonederivatives AT marinaazevedosouza antimicrobialactivityoflapacholanditsthiosemicarbazoneandsemicarbazonederivatives AT susanajohann antimicrobialactivityoflapacholanditsthiosemicarbazoneandsemicarbazonederivatives AT lucianaalvesrodriguesdossantoslima antimicrobialactivityoflapacholanditsthiosemicarbazoneandsemicarbazonederivatives AT fernandafragacampos antimicrobialactivityoflapacholanditsthiosemicarbazoneandsemicarbazonederivatives AT isoldacastromendes antimicrobialactivityoflapacholanditsthiosemicarbazoneandsemicarbazonederivatives AT heloisaberaldo antimicrobialactivityoflapacholanditsthiosemicarbazoneandsemicarbazonederivatives AT elainemariadesouzafagundes antimicrobialactivityoflapacholanditsthiosemicarbazoneandsemicarbazonederivatives AT patriciasilvacisalpino antimicrobialactivityoflapacholanditsthiosemicarbazoneandsemicarbazonederivatives AT carlosaugustorosa antimicrobialactivityoflapacholanditsthiosemicarbazoneandsemicarbazonederivatives AT taniamariadealmeidaalves antimicrobialactivityoflapacholanditsthiosemicarbazoneandsemicarbazonederivatives AT niveapereiradesa antimicrobialactivityoflapacholanditsthiosemicarbazoneandsemicarbazonederivatives AT carlosleomarzani antimicrobialactivityoflapacholanditsthiosemicarbazoneandsemicarbazonederivatives |