PAGES: 342-351 DOI: 10.1590/0074-0276108032013013 Full paper
The antimicrobial activity of lapachol and its thiosemicarbazone and semicarbazone derivatives

Marina Azevêdo Souza1, Susana Johann1,2,+, Luciana Alves Rodrigues dos Santos Lima3, Fernanda Fraga Campos1,2, Isolda Castro Mendes4, Heloisa Beraldo5, Elaine Maria de Souza-Fagundes6, Patrícia Silva Cisalpino2, Carlos Augusto Rosa2, Tânia Maria de Almeida Alves1, Nívea Pereira de Sá2, Carlos Leomar Zani1

1Laboratório de Química de Produtos Naturais, Centro de Pesquisas René Rachou-Fiocruz, Belo Horizonte, MG, Brasil
2Departamento de Microbiologia 6Departamento de Fisiologia e Biofísica, Instituto de Ciências Biológicas
4Escola de Belas Artes
5Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, Belo Horizonte, MG, Brasil
3Universidade Federal de São João Del Rei, Campus Centro Oeste Dona Lindu, Divinópolis, MG, Brasil


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.

Received 27 June 2012
Accepted 19 September 2012
+ Corresponding author: This e-mail address is being protected from spambots. You need JavaScript enabled to view it.


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