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Synthesis, modeling and biological activity of new zinc(II) hydroxamates against streptococcus pneumoniae

2019; Elsevier BV; Volume: 22; Linguagem: Inglês

10.1016/j.cdc.2019.100240

2405-8300

Bruna Lisboa Gonçalves, Daniela Fernandes Ramos, Priscila Cristina Bartolomeu Halicki, Pedro Eduardo Almeida da Silva, Juliano Rosa de Menezes Vicenti,

Synthesis and biological activity

In this paper we report the synthesis and characterization of the following aromatic hydroxamates: potassium(I) benzohydroxamate (BZH), potassium(I) nitrobenzohydroxamate (N-BZH), potassium(I) dinitrobenzohydroxamate (DN-BZH) and the complexes derived containing zinc(II): BZH-Zn, N-BZH-Zn and DN-BZH-Zn. The compounds were characterized and their probable structures proposed using infrared spectroscopy, nuclear magnetic resonance spectroscopy, thermogravimetry and elemental analysis. Calculations of HOMO and LUMO pointed out that DN-BZH anion is the most reactive specie, once it presented the lowest value of energy gap, ca. of 7.65 eV. The compounds were evaluated against Streptococcus pneumoniae, Escherichia coli, Staphylococcus aureus and Pseudomonas aeruginosa. It was possible to observe that DN-BZH demonstrated a minimum inhibitory concentration (MIC) of 25 µg/mL, while its zinc(II) complex presented a MIC of 12.5 µg/mL for S. pneumoniae. Molecular docking studies performed with an urease model suggested coordination between the hydroxamic fraction of DN-BZH and nickel(II) ions located in the active site, showing a bond length of approximately 2.3 Å and a variety of interactions with specific amino acids residues.