Portal de Periódicos da CAPES

Artigo Produção Nacional Revisado por pares

BIBTEX RIS

Structural characterization, DFT calculations, ADMET studies, antibiotic potentiating activity, evaluation of efflux pump inhibition and molecular docking of chalcone (E)-1-(2-hydroxy-3,4,6-trimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one

2020; Elsevier BV; Volume: 1227; Linguagem: Inglês

10.1016/j.molstruc.2020.129692

1872-8014

Jayze da Cunha Xavier, Francisco Wagner Queiroz Almeida-Neto, Priscila Teixeira da Silva, Amanda Pereira de Sousa, Emmanuel Silva Marinho, Márcia Machado Marinho, Janaína Esmeraldo Rocha, Priscila Ramos Freitas, Ana Carolina Justino de Araújo, Thiago Santiago Freitas, C.E.S. Nogueira, Pedro de Lima‐Neto, Paulo Nogueira Bandeira, Alexandre Magno Rodrigues Teixeira, Henrique Douglas Melo Coutinho, Hélcio Silva dos Santos,

Bioactive Compounds and Antitumor Agents

Chalcones are open-chain flavonoids characterized by two aromatic rings joined by a three-carbon α,β-unsaturated carbonyl system. Over the last several years, chalcones have instigated the interest of chemical and pharmacological researchers due to their simple chemical structure and varied biological activities. Here, we performed the electronic properties, of the chalcone, (E)-1-(2-hydroxy-3,4,6-trimethoxyphenyl)-3-(4-methoxyphenyl) prop-2-en-1-one synthesized by Claisen-Schmidt condensation reaction. The density functional theory method was used with the B3LYP/6-311++G(d,p) level of theory to compute the structural, electronic, and reactivity properties of the chalcone. In addition, microbiological tests were performed to investigate the modulator potential and efflux pump inhibition on Staphylococcus aureus multi-resistant strains. The spectroscopic data analyses allowed drawing the molecular structure of the chalcone synthetized with subsequent confirmation using the quantum chemical calculations. The addition of chalcone to the growth medium caused a synergic effect by reduction of the minimum inhibitory concentration (MIC) values for ciprofloxacin strain. Docking results showed that the chalcone docks in almost the same way as the antibiotic against a MepA model. Druglikeness criteria based on the rules of Lipinski and Veber evaluated that the chalcone has the ideal physicochemical and pharmacokinetic properties to be a good candidate for drug orally. The results confirm the structure of the synthesized chalcone and revealing that the compound can be used as a possible inhibitor of the Mep A efflux pump.