Antimicrobial activity of quinoxaline 1,4-dioxide with 2- and 3-substituted derivatives.
Quinoxaline is a chemical compound that presents a structure that is similar to quinolone antibiotics. The present work reports the study of the antimicrobial activity of quinoxaline N,N-dioxide and some derivatives against bacterial and yeast strains. The compounds studied were quinoxaline-1,4-dioxide (QNX), 2-methylquinoxaline-1,4-dioxide (2MQNX), 2-methyl-3-benzoylquinoxaline-1,4-dioxide (2M3BenzoylQNX), 2-methyl-3-benzylquinoxaline-1,4-dioxide (2M3BQNX), 2-amino-3-cyanoquinoxaline-1,4-dioxide (2A3CQNX), 3-methyl-2-quinoxalinecarboxamide-1,4-dioxide (3M2QNXC), 2-hydroxyphenazine-N,N-dioxide (2HF) and 3-methyl-N-(2-methylphenyl)quinoxalinecarboxamide-1,4-dioxide (3MN(2MF)QNXC). The prokaryotic strains used were Staphylococcus aureus ATCC 6538, S. aureus ATCC 6538P, S. aureus ATCC 29213, Escherichia coli ATCC 25922, E. coli S3R9, E. coli S3R22, E. coli TEM-1 CTX-M9, E. coli TEM-1, E. coli AmpC Mox-2, E. coli CTX-M2 e E. coli CTX-M9. The Candida albicans ATCC 10231 and Saccharomyces cerevisiae PYCC 4072 were used as eukaryotic strains. For the compounds that presented activity using the disk diffusion method, the minimum inhibitory concentration (MIC) was determined. The alterations of cellular viability were evaluated in a time-course assay. Death curves for bacteria and growth curves for S. cerevisiae PYCC 4072 were also accessed. The results obtained suggest potential new drugs for antimicrobial activity chemotherapy since the MIC's determined present low values and cellular viability tests show the complete elimination of the bacterial strain. Also, the cellular viability tests for the eukaryotic model, S. cerevisiae, indicate low toxicity for the compounds tested.
REQUIMTE/CQFB, Departamento de Química, FCT, Universidade Nova de Lisboa, 2829-516 Caparica, Portugal; Ciências Químicas e das Biomoléculas, Centro de Investigação em Saúde e Ambiente, Escola Superior de Tecnologias da Saúde, Instituto Politécnico do Porto, Rua Valente Perfeito, 322, 4400-330 Vila Nova de Gaia, Portugal. Electronic address: mav@estsp.ipp.pt.
Mónica
M
Vieira
Ciências Químicas e das Biomoléculas, Centro de Investigação em Saúde e Ambiente, Escola Superior de Tecnologias da Saúde, Instituto Politécnico do Porto, Rua Valente Perfeito, 322, 4400-330 Vila Nova de Gaia, Portugal.
Cátia
C
Pinheiro
Ciências Químicas e das Biomoléculas, Centro de Investigação em Saúde e Ambiente, Escola Superior de Tecnologias da Saúde, Instituto Politécnico do Porto, Rua Valente Perfeito, 322, 4400-330 Vila Nova de Gaia, Portugal; Centro de Farmacologia e Biopatologia Química (U38-FCT), Faculdade de Medicina, Universidade do Porto, Alameda Prof. Hernâni Monteiro, 4200-319 Porto, Portugal.
Rúben
R
Fernandes
REQUIMTE/CQFB, Departamento de Química, FCT, Universidade Nova de Lisboa, 2829-516 Caparica, Portugal.
João Paulo
JP
Noronha
Ciências Químicas e das Biomoléculas, Centro de Investigação em Saúde e Ambiente, Escola Superior de Tecnologias da Saúde, Instituto Politécnico do Porto, Rua Valente Perfeito, 322, 4400-330 Vila Nova de Gaia, Portugal; Centro de Farmacologia e Biopatologia Química (U38-FCT), Faculdade de Medicina, Universidade do Porto, Alameda Prof. Hernâni Monteiro, 4200-319 Porto, Portugal; CHUC, Centro Hospitalar da Universidade de Coimbra, Coimbra, Portugal.
Cristina
C
Prudêncio
D000890:Anti-Infective Agents / Q000737:chemistry / Q000494:pharmacology*; D002176:Candida albicans / Q000187:drug effects*; D004926:Escherichia coli / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D050296:Microbial Viability / Q000187:drug effects; D011810:Quinoxalines / Q000737:chemistry / Q000494:pharmacology*; D012441:Saccharomyces cerevisiae / Q000187:drug effects*; D013211:Staphylococcus aureus / Q000187:drug effects*
D000890:Anti-Infective Agents; D011810:Quinoxalines; C003282:quindoxin
Antimicrobial activity; Cellular viability; Minimum inhibitory concentration; Quinoxaline N,N-dioxide derivatives