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dc.contributor.author
Osorio, Mauricio
dc.contributor.author
Carvajal, Marcela
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Vergara, Alejandra
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Butassi, Estefanía
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dc.contributor.author
Zacchino, Susana Alicia Stella
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Mascayano, Carolina
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Montoya, Margarita
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Mejías, Sophia
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Cortés San Martín, Marcelo
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Vásquez Martínez, Yesseny
dc.date.available
2022-08-03T14:45:16Z
dc.date.issued
2021-05
dc.identifier.citation
Osorio, Mauricio; Carvajal, Marcela; Vergara, Alejandra; Butassi, Estefanía; Zacchino, Susana Alicia Stella; et al.; Prenylated flavonoids with potential antimicrobial activity: synthesis, biological activity, and in silico study; Multidisciplinary Digital Publishing Institute; International Journal of Molecular Sciences; 22; 11; 5-2021; 1-22
dc.identifier.issn
1422-0067
dc.identifier.uri
http://hdl.handle.net/11336/164040
dc.description.abstract
Prenylated flavonoids are an important class of naturally occurring flavonoids with important biological activity, but their low abundance in nature limits their application in medicines. Here, we showed the hemisynthesis and the determination of various biological activities of seven prenylated flavonoids, named 7–13, with an emphasis on antimicrobial ones. Compounds 9, 11, and 12 showed inhibitory activity against human pathogenic fungi. Compounds 11, 12 (flavanones) and 13 (isoflavone) were the most active against clinical isolated Staphylococcus aureus MRSA, showing that structural requirements as prenylation at position C-6 or C-8 and OH at positions C-5, 7, and 4′ are key to the antibacterial activity. The combination of 11 or 12 with commercial antibiotics synergistically enhanced the antibacterial activity of vancomycin, ciprofloxacin, and methicillin in a factor of 10 to 100 times against drug-resistant bacteria. Compound 11 combined with ciprofloxacin was able to decrease the levels of ROS generated by ciprofloxacin. According to docking results of S enantiomer of 11 with ATP-binding cassette transporter showed the most favorable binding energy; however, more studies are needed to support this result.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Multidisciplinary Digital Publishing Institute
dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by/2.5/ar/
dc.subject
ANTIBACTERIAL
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ANTIFUNGAL
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MRSA
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PRENYLATED FLAVONOIDS
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SYNERGISM
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SYNTHESIS
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Química Orgánica
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Ciencias Químicas
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CIENCIAS NATURALES Y EXACTAS
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dc.title
Prenylated flavonoids with potential antimicrobial activity: synthesis, biological activity, and in silico study
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2022-08-02T18:13:54Z
dc.journal.volume
22
dc.journal.number
11
dc.journal.pagination
1-22
dc.journal.pais
Suiza
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dc.journal.ciudad
Basilea
dc.description.fil
Fil: Osorio, Mauricio. Universidad Técnica Federico Santa María; Chile
dc.description.fil
Fil: Carvajal, Marcela. Universidad Técnica Federico Santa María; Chile
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Fil: Vergara, Alejandra. Universidad Técnica Federico Santa María; Chile
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Fil: Butassi, Estefanía. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina
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Fil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina
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Fil: Mascayano, Carolina. Universidad de Santiago de Chile; Chile
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Fil: Montoya, Margarita. Universidad de Santiago de Chile; Chile
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Fil: Mejías, Sophia. Universidad de Santiago de Chile; Chile
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Fil: Cortés San Martín, Marcelo. Universidad de Santiago de Chile; Chile
dc.description.fil
Fil: Vásquez Martínez, Yesseny. Universidad de Santiago de Chile; Chile
dc.journal.title
International Journal of Molecular Sciences
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dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/1422-0067/22/11/5472
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/https://doi.org/10.3390/ijms22115472
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