Antibacterial Activity of 2-Amino-1,4-naphthoquinone Derivatives against Gram-Positive and Gram-Negative Bacterial Strains and Their Interaction with Human Serum Albumin

dc.creatorSilva, Carla C. da
dc.creatorChaves, Otávio A.
dc.creatorPaiva, Rojane O.
dc.creatorCosta, Gisela L. da
dc.creatorFerreira, José Carlos Netto
dc.creatorEchevarria, Aurea
dc.date2020-08-08T19:13:09Z
dc.date2020-08-08T19:13:09Z
dc.date2020
dc.date.accessioned2023-09-26T22:27:11Z
dc.date.available2023-09-26T22:27:11Z
dc.identifierSILVA, Carla C. da et al. Antibacterial Activity of 2-Amino-1,4-naphthoquinone Derivatives against Gram-Positive and Gram-Negative Bacterial Strains and Their Interaction with Human Serum Albumin. Journal of the Brazilian Chemical Society, v. 31, n. 9, p. 1838-1851, 2020.
dc.identifier0103-5053
dc.identifierhttps://www.arca.fiocruz.br/handle/icict/42600
dc.identifier10.21577/0103-5053.20200070
dc.identifier.urihttps://repositorioslatinoamericanos.uchile.cl/handle/2250/8879410
dc.descriptionA series of 2-amino-1,4-naphthoquinone derivatives (NQA-NQF) was synthesized by alternative methods (ultrasonication and microwave irradiation), with yields ranging from 40 to 71%, and without the need of further recrystallization. Each compound was evaluated against four Gram-positive (Bacillus subtilis, Enterococcus faecalis, Staphylococcus aureus and Bacillus cereus) and five Gram-negative (Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, Acinetobacter baumannii and Klebsiella pneumoniae positive β-lactamase) bacteria strains. The NQF was the most active amino-naphthoquinone derivative with minimum inhibitory concentration (MIC) of 31.2 µg mL-1 against K. pneumoniae positive β-lactamase (a common intestinal bacteria which can cause life-threatening infections). On the other hand, NQA and NQC showed good activity as a potential antibiotic for the bacteria strains assayed, except for K. pneumoniae. In addition, the affinity of these three most active compounds (NQA, NQC, and NQF) for human serum albumin (HSA) was evaluated employing multiple spectroscopic techniques (steady-state, time-resolved, and synchronous fluorescence, as well as circular dichroism), combined with theoretical calculations (molecular docking). The interaction HSA:2-amino-1,4-naphthoquinones occurs spontaneously and moderately inside the subdomain IIA (Sudlow’s site I) via hydrogen bonding and van der Waals forces.
dc.formatapplication/pdf
dc.languageeng
dc.publisherSociedade Brasileira de Química
dc.rightsopen access
dc.subject2-amino-1,4-naftoquinonas
dc.subjectAgente antibacteriano
dc.subjectAlbumina sérica humana
dc.subjectEspectroscopia
dc.subjectDocking molecular
dc.subject2-amino-1,4-naphthoquinones
dc.subjectAntibacterial agent
dc.subjectHuman serum albumin
dc.subjectSpectroscopy
dc.subjectMolecular docking
dc.titleAntibacterial Activity of 2-Amino-1,4-naphthoquinone Derivatives against Gram-Positive and Gram-Negative Bacterial Strains and Their Interaction with Human Serum Albumin
dc.typeArticle


Este ítem pertenece a la siguiente institución