Publicado

2020-01-01

Antibacterial, antifungal, and antiviral activities of chalcone-bearing tetrahydropyranyl and 2,4-dihydroxyl moieties

Actividad antibacteriana, antifungica y antiviral de las chalconas que contienen los grupos tetrahidropiranilo y 2,4-dihidroxilo

DOI:

https://doi.org/10.15446/rcciquifa.v49n1.87036

Palabras clave:

Phenolic compounds, antifungal activity, Candida albicans, antiviral activity, dengue virus, antibacterial activity (en)
Compuestos fenólicos, actividad antifúngica, Candida albicans, actividad antiviral, virus del dengue, actividad antibacterian (es)

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Autores/as

  • William Gustavo Lima Laboratório de Microbiologia Médica, Universidade Federal de São João del-Rei, Campus Centro-Oeste Dona Lindu, Divinópolis-MG
  • Jéssica Tauany Andrade Laboratório de Microbiologia Médica, Universidade Federal de São João del-Rei, Campus Centro-Oeste Dona Lindu, Divinópolis-MG
  • Felipe Rocha da Silva Santos Laboratório de Síntese Orgânica e Nanoestruturas, Universidade Federal de São João del-Rei, Campus Centro-Oeste Dona Lindu, Divinópolis-MG
  • Juliana Maria Campos Palumbo Laboratório de Microbiologia Médica, Universidade Federal de São João del-Rei, Campus Centro-Oeste Dona Lindu, Divinópolis-MG
  • Karina Marjorie Silva Herrera Laboratório de Microbiologia Médica, Universidade Federal de São João del-Rei, Campus Centro-Oeste Dona Lindu, Divinópolis-MG
  • Laurieny Eloína de Castro Laboratório de Microbiologia Médica, Universidade Federal de São João del-Rei, Campus Centro-Oeste Dona Lindu, Divinópolis-MG
  • Fernanda Bárbara de Morais aboratório de Microbiologia Médica, Universidade Federal de São João del-Rei, Campus Centro-Oeste Dona Lindu, Divinópolis-MG
  • Mayra Karla Prates da Silva aboratório de Microbiologia Médica, Universidade Federal de São João del-Rei, Campus Centro-Oeste Dona Lindu, Divinópolis-MGaboratório de Microbiologia Médica, Universidade Federal de São João del-Rei, Campus Centro-Oeste Dona Lindu, Divinópolis-MG
  • José Augusto Ferreira Perez Villar Laboratório de Síntese Orgânica e Nanoestruturas, Universidade Federal de São João del-Rei, Campus Centro-Oeste Dona Lindu, Divinópolis-MG
  • Jaqueline Maria Siqueira Ferreira Laboratório de Microbiologia Médica, Universidade Federal de São João del-Rei, Campus Centro-Oeste Dona Lindu, Divinópolis-MG

Chalcones highlights as an important structure in medicinal chemistry and thus has been widely used as a template in the development of new drugs. In this study, we aim to determine the antibacterial, anti-Candida, and anti-Dengue potential of new chalcone-bearing 2,4-dihydroxyl and tetrahydropyranyl moieties. Antimicrobial activity assays showed that microorganism of the Staphylococcus genus (including methicillin-resistant strains) were susceptible to 2,4-dihydroxychalcones, with minimum inhibitory concentrations (MICs) ranging of 19.5 to 125 µg.mL-1. Compound 4e, which showed the highest bacteriostatic effect, also has bactericidal activity from of 80 µg.mL-1. The growth of oral isolates of Candida albicans was also efficiently inhibited with compound 4e (MIC: 15.6–32.3 µg.mL-1), which was fungicidal at 15.6 µg.mL-1. However, the presence of the tetrahydropyranyl moiety impaired both the antibacterial and antifungal effects. None of the chalcones tested were actives against Dengue virus serotype 2. In conclusion, the compound 4e showed good anti-Staphylococci and anti-Candida activity and may be a promising prototype for the development of new antimicrobial agents.

Las chalconas se destacan como una estructura importante en la química médica y, por lo tanto, se ha empleado como prototipo para el desarrollo de nuevos fármacos. En este estudio, nuestro objetivo fue determinar el potencial antibacteriano, anti-Candida y anti-Dengue de las nuevas chalconas que poseen los grupos 2,4-dihidroxilo y tetrahidropiranilo. El ensayo de actividad antimicrobiana mostró que las bacterias del género Staphylococcus (incluidas las cepas resistentes a la meticilina) fueron sensibles a las 2,4-dihidroxicalconas estudiadas, con concentraciones inhibitorias mínimas (CIM) que oscilan entre 19,5 y 125 μg.mL-1. El compuesto 4e, que tuvo el mejor efecto bacteriostático, también mostró un efecto bactericida a partir de la concentración de 80 μg.mL-1. El crecimiento de los aislamientos orales de Candida albicans también se inhibió eficientemente con el compuesto 4e (CIM: 15.6-32.3 μg.mL-1), que fue fungicida a una concentración de 15.6 μg.mL-1. Sin embargo, la presencia del grupo tetrahidropiranilo perjudicó la actividad antibacteriana y antifúngica de los análogos de la chalcona. Además, ninguno de los compuestos evaluados mostró un efecto contra el virus del dengue serotipo 2. En conclusión, el compuesto 4e muestra una buena actividad anti-estafilocócica y anti-Candida y puede ser un prototipo prometedor para el desarrollo de nuevos agentes antimicrobianos.

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Cómo citar

APA

Lima, W. G., Andrade, J. T., Rocha da Silva Santos, F., Campos Palumbo, J. M., Silva Herrera, K. M., de Castro, L. E., de Morais, F. B., Prates da Silva, M. K., Ferreira Perez Villar, J. A. y Siqueira Ferreira, J. M. (2020). Antibacterial, antifungal, and antiviral activities of chalcone-bearing tetrahydropyranyl and 2,4-dihydroxyl moieties. Revista Colombiana de Ciencias Químico-Farmacéuticas, 49(1). https://doi.org/10.15446/rcciquifa.v49n1.87036

ACM

[1]
Lima, W.G., Andrade, J.T., Rocha da Silva Santos, F., Campos Palumbo, J.M., Silva Herrera, K.M., de Castro, L.E., de Morais, F.B., Prates da Silva, M.K., Ferreira Perez Villar, J.A. y Siqueira Ferreira, J.M. 2020. Antibacterial, antifungal, and antiviral activities of chalcone-bearing tetrahydropyranyl and 2,4-dihydroxyl moieties. Revista Colombiana de Ciencias Químico-Farmacéuticas. 49, 1 (ene. 2020). DOI:https://doi.org/10.15446/rcciquifa.v49n1.87036.

ACS

(1)
Lima, W. G.; Andrade, J. T.; Rocha da Silva Santos, F.; Campos Palumbo, J. M.; Silva Herrera, K. M.; de Castro, L. E.; de Morais, F. B.; Prates da Silva, M. K.; Ferreira Perez Villar, J. A.; Siqueira Ferreira, J. M. Antibacterial, antifungal, and antiviral activities of chalcone-bearing tetrahydropyranyl and 2,4-dihydroxyl moieties. Rev. Colomb. Cienc. Quím. Farm. 2020, 49.

ABNT

LIMA, W. G.; ANDRADE, J. T.; ROCHA DA SILVA SANTOS, F.; CAMPOS PALUMBO, J. M.; SILVA HERRERA, K. M.; DE CASTRO, L. E.; DE MORAIS, F. B.; PRATES DA SILVA, M. K.; FERREIRA PEREZ VILLAR, J. A.; SIQUEIRA FERREIRA, J. M. Antibacterial, antifungal, and antiviral activities of chalcone-bearing tetrahydropyranyl and 2,4-dihydroxyl moieties. Revista Colombiana de Ciencias Químico-Farmacéuticas, [S. l.], v. 49, n. 1, 2020. DOI: 10.15446/rcciquifa.v49n1.87036. Disponível em: https://revistas.unal.edu.co/index.php/rccquifa/article/view/87036. Acesso em: 21 may. 2024.

Chicago

Lima, William Gustavo, Jéssica Tauany Andrade, Felipe Rocha da Silva Santos, Juliana Maria Campos Palumbo, Karina Marjorie Silva Herrera, Laurieny Eloína de Castro, Fernanda Bárbara de Morais, Mayra Karla Prates da Silva, José Augusto Ferreira Perez Villar, y Jaqueline Maria Siqueira Ferreira. 2020. «Antibacterial, antifungal, and antiviral activities of chalcone-bearing tetrahydropyranyl and 2,4-dihydroxyl moieties». Revista Colombiana De Ciencias Químico-Farmacéuticas 49 (1). https://doi.org/10.15446/rcciquifa.v49n1.87036.

Harvard

Lima, W. G., Andrade, J. T., Rocha da Silva Santos, F., Campos Palumbo, J. M., Silva Herrera, K. M., de Castro, L. E., de Morais, F. B., Prates da Silva, M. K., Ferreira Perez Villar, J. A. y Siqueira Ferreira, J. M. (2020) «Antibacterial, antifungal, and antiviral activities of chalcone-bearing tetrahydropyranyl and 2,4-dihydroxyl moieties», Revista Colombiana de Ciencias Químico-Farmacéuticas, 49(1). doi: 10.15446/rcciquifa.v49n1.87036.

IEEE

[1]
W. G. Lima, «Antibacterial, antifungal, and antiviral activities of chalcone-bearing tetrahydropyranyl and 2,4-dihydroxyl moieties», Rev. Colomb. Cienc. Quím. Farm., vol. 49, n.º 1, ene. 2020.

MLA

Lima, W. G., J. T. Andrade, F. Rocha da Silva Santos, J. M. Campos Palumbo, K. M. Silva Herrera, L. E. de Castro, F. B. de Morais, M. K. Prates da Silva, J. A. Ferreira Perez Villar, y J. M. Siqueira Ferreira. «Antibacterial, antifungal, and antiviral activities of chalcone-bearing tetrahydropyranyl and 2,4-dihydroxyl moieties». Revista Colombiana de Ciencias Químico-Farmacéuticas, vol. 49, n.º 1, enero de 2020, doi:10.15446/rcciquifa.v49n1.87036.

Turabian

Lima, William Gustavo, Jéssica Tauany Andrade, Felipe Rocha da Silva Santos, Juliana Maria Campos Palumbo, Karina Marjorie Silva Herrera, Laurieny Eloína de Castro, Fernanda Bárbara de Morais, Mayra Karla Prates da Silva, José Augusto Ferreira Perez Villar, y Jaqueline Maria Siqueira Ferreira. «Antibacterial, antifungal, and antiviral activities of chalcone-bearing tetrahydropyranyl and 2,4-dihydroxyl moieties». Revista Colombiana de Ciencias Químico-Farmacéuticas 49, no. 1 (enero 1, 2020). Accedido mayo 21, 2024. https://revistas.unal.edu.co/index.php/rccquifa/article/view/87036.

Vancouver

1.
Lima WG, Andrade JT, Rocha da Silva Santos F, Campos Palumbo JM, Silva Herrera KM, de Castro LE, de Morais FB, Prates da Silva MK, Ferreira Perez Villar JA, Siqueira Ferreira JM. Antibacterial, antifungal, and antiviral activities of chalcone-bearing tetrahydropyranyl and 2,4-dihydroxyl moieties. Rev. Colomb. Cienc. Quím. Farm. [Internet]. 1 de enero de 2020 [citado 21 de mayo de 2024];49(1). Disponible en: https://revistas.unal.edu.co/index.php/rccquifa/article/view/87036

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