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
| Autor: | Janaína Esmeraldo Rocha, Alexandre Magno Rodrigues Teixeira, Ana Carolina Justino de Araújo, Amanda Pereira de Sousa, Priscila Teixeira da Silva, Jayze da Cunha Xavier, Priscila R. Freitas, Carlos Emídio Sampaio Nogueira, Paulo Nogueira Bandeira, Márcia Machado Marinho, Emmanuel Silva Marinho, Thiago Santiago Freitas, Francisco Wagner de Queiroz Almeida-Neto, Pedro de Lima-Neto, Hélcio Silva dos Santos, Henrique Douglas Melo Coutinho |
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| Rok vydání: | 2021 |
| Předmět: |
Chalcone
010405 organic chemistry Stereochemistry Chemistry Chemical structure Organic Chemistry 010402 general chemistry Druglikeness Condensation reaction 01 natural sciences 0104 chemical sciences Analytical Chemistry Inorganic Chemistry chemistry.chemical_compound Minimum inhibitory concentration Docking (molecular) Molecule Efflux Spectroscopy |
| Zdroj: | Journal of Molecular Structure. 1227:129692 |
| ISSN: | 0022-2860 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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