A novel bis(pyrazolyl)methane compound as a potential agent against Gram-positive bacteria
Abstract This study was designed to propose alternative therapeutic compounds to fight against bacterial pathogens. Thus, a library of nitrogen-based compounds bis(triazolyl)methane (1T–7T) and bis(pyrazolyl)methane (1P–11P) was synthesised following previously reported methodologies and their antib...
| Main Authors: | , , , , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2021-08-01
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| Series: | Scientific Reports |
| Online Access: | https://doi.org/10.1038/s41598-021-95609-z |
| _version_ | 1831574228780974080 |
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| author | Pedro Seguí John J. Aguilera-Correa Elena Domínguez-Jurado Christian M. Sánchez-López Ramón Pérez-Tanoira Ana V. Ocaña José A. Castro-Osma Jaime Esteban Antonio Marcilla Carlos Alonso-Moreno Francisco C. Pérez-Martínez Milagros Molina-Alarcón |
| author_facet | Pedro Seguí John J. Aguilera-Correa Elena Domínguez-Jurado Christian M. Sánchez-López Ramón Pérez-Tanoira Ana V. Ocaña José A. Castro-Osma Jaime Esteban Antonio Marcilla Carlos Alonso-Moreno Francisco C. Pérez-Martínez Milagros Molina-Alarcón |
| author_sort | Pedro Seguí |
| collection | DOAJ |
| description | Abstract This study was designed to propose alternative therapeutic compounds to fight against bacterial pathogens. Thus, a library of nitrogen-based compounds bis(triazolyl)methane (1T–7T) and bis(pyrazolyl)methane (1P–11P) was synthesised following previously reported methodologies and their antibacterial activity was tested using the collection strains of Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, and Pseudomonas aeruginosa. Moreover, the novel compound 2P was fully characterized by IR, UV–Vis and NMR spectroscopy. To evaluate antibacterial activity, minimal inhibitory concentrations (MICs), minimal bactericidal concentrations (MBCs), minimum biofilm inhibitory concentrations (MBICs), and minimum biofilm eradication concentrations (MBECs) assays were carried out at different concentrations (2–2000 µg/mL). The MTT assay and Resazurin viability assays were performed in both human liver carcinoma HepG2 and human colorectal adenocarcinoma Caco-2 cell lines at 48 h. Of all the synthesised compounds, 2P had an inhibitory effect on Gram-positive strains, especially against S. aureus. The MIC and MBC of 2P were 62.5 and 2000 µg/mL against S. aureus, and 250 and 2000 µg/mL against E. faecalis, respectively. However, these values were > 2000 µg/mL against E. coli and P. aeruginosa. In addition, the MBICs and MBECs of 2P against S. aureus were 125 and > 2000 µg/mL, respectively, whereas these values were > 2000 µg/mL against E. faecalis, E. coli, and P. aeruginosa. On the other hand, concentrations up to 250 µg/mL of 2P were non-toxic doses for eukaryotic cell cultures. Thus, according to the obtained results, the 2P nitrogen-based compound showed a promising anti-Gram-positive effect (especially against S. aureus) both on planktonic state and biofilm, at non-toxic concentrations. |
| first_indexed | 2024-12-17T13:59:22Z |
| format | Article |
| id | doaj.art-d7cf4a045fdd4394aaba1c44da275b66 |
| institution | Directory Open Access Journal |
| issn | 2045-2322 |
| language | English |
| last_indexed | 2024-12-17T13:59:22Z |
| publishDate | 2021-08-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Scientific Reports |
| spelling | doaj.art-d7cf4a045fdd4394aaba1c44da275b662022-12-21T21:45:50ZengNature PortfolioScientific Reports2045-23222021-08-0111111010.1038/s41598-021-95609-zA novel bis(pyrazolyl)methane compound as a potential agent against Gram-positive bacteriaPedro Seguí0John J. Aguilera-Correa1Elena Domínguez-Jurado2Christian M. Sánchez-López3Ramón Pérez-Tanoira4Ana V. Ocaña5José A. Castro-Osma6Jaime Esteban7Antonio Marcilla8Carlos Alonso-Moreno9Francisco C. Pérez-Martínez10Milagros Molina-Alarcón11Department of Otorhinolaryngology, Complejo Hospitalario UniversitarioClinical Microbiology Department, IIS-Fundacion Jimenez Diaz-UAMNanoCRIB Unit, Centro Regional de Investigaciones BiomédicasDepartment of Farmàcia i Tecnologia Farmacèutica i Parasitologia, University of ValenciaClinical Microbiology Department, Hospital Universitario Príncipe de AsturiasInstituto de Investigación en Discapacidades Neurológicas (IDINE), University of Castilla-La ManchaNanoCRIB Unit, Centro Regional de Investigaciones BiomédicasClinical Microbiology Department, IIS-Fundacion Jimenez Diaz-UAMDepartment of Farmàcia i Tecnologia Farmacèutica i Parasitologia, University of ValenciaNanoCRIB Unit, Centro Regional de Investigaciones BiomédicasInstituto de Investigación en Discapacidades Neurológicas (IDINE), University of Castilla-La ManchaInstituto de Investigación en Discapacidades Neurológicas (IDINE), University of Castilla-La ManchaAbstract This study was designed to propose alternative therapeutic compounds to fight against bacterial pathogens. Thus, a library of nitrogen-based compounds bis(triazolyl)methane (1T–7T) and bis(pyrazolyl)methane (1P–11P) was synthesised following previously reported methodologies and their antibacterial activity was tested using the collection strains of Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, and Pseudomonas aeruginosa. Moreover, the novel compound 2P was fully characterized by IR, UV–Vis and NMR spectroscopy. To evaluate antibacterial activity, minimal inhibitory concentrations (MICs), minimal bactericidal concentrations (MBCs), minimum biofilm inhibitory concentrations (MBICs), and minimum biofilm eradication concentrations (MBECs) assays were carried out at different concentrations (2–2000 µg/mL). The MTT assay and Resazurin viability assays were performed in both human liver carcinoma HepG2 and human colorectal adenocarcinoma Caco-2 cell lines at 48 h. Of all the synthesised compounds, 2P had an inhibitory effect on Gram-positive strains, especially against S. aureus. The MIC and MBC of 2P were 62.5 and 2000 µg/mL against S. aureus, and 250 and 2000 µg/mL against E. faecalis, respectively. However, these values were > 2000 µg/mL against E. coli and P. aeruginosa. In addition, the MBICs and MBECs of 2P against S. aureus were 125 and > 2000 µg/mL, respectively, whereas these values were > 2000 µg/mL against E. faecalis, E. coli, and P. aeruginosa. On the other hand, concentrations up to 250 µg/mL of 2P were non-toxic doses for eukaryotic cell cultures. Thus, according to the obtained results, the 2P nitrogen-based compound showed a promising anti-Gram-positive effect (especially against S. aureus) both on planktonic state and biofilm, at non-toxic concentrations.https://doi.org/10.1038/s41598-021-95609-z |
| spellingShingle | Pedro Seguí John J. Aguilera-Correa Elena Domínguez-Jurado Christian M. Sánchez-López Ramón Pérez-Tanoira Ana V. Ocaña José A. Castro-Osma Jaime Esteban Antonio Marcilla Carlos Alonso-Moreno Francisco C. Pérez-Martínez Milagros Molina-Alarcón A novel bis(pyrazolyl)methane compound as a potential agent against Gram-positive bacteria Scientific Reports |
| title | A novel bis(pyrazolyl)methane compound as a potential agent against Gram-positive bacteria |
| title_full | A novel bis(pyrazolyl)methane compound as a potential agent against Gram-positive bacteria |
| title_fullStr | A novel bis(pyrazolyl)methane compound as a potential agent against Gram-positive bacteria |
| title_full_unstemmed | A novel bis(pyrazolyl)methane compound as a potential agent against Gram-positive bacteria |
| title_short | A novel bis(pyrazolyl)methane compound as a potential agent against Gram-positive bacteria |
| title_sort | novel bis pyrazolyl methane compound as a potential agent against gram positive bacteria |
| url | https://doi.org/10.1038/s41598-021-95609-z |
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