1. Synthesis, structural and spectroscopic characterization, in silico study, and antinociceptive effect in adult zebrafish of 2-(4-isobutylphenyl) -N'-phenylpropanohydrazide
- Author
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João Pedro da Hora, Márcia Machado Marinho, Antonio Wlisses da Silva, Francisco W.Q. Almeida-Neto, Paulo Freire, Tigressa Helena Soares Rodrigues, Jane Eire Silva Alencar de Menezes, Amanda Pereira de Sousa, Hélcio Silva dos Santos, Murilo Sérgio da Silva Julião, Paulo Nogueira Bandeira, Emmanuel Silva Marinho, Aldeneide Soares de Paiva, A. C. H. Barreto, Maria Kueirislene Amâncio Ferreira, Tatiana Rodrigues Garcia, and Alexandre Magno Rodrigues Teixeira
- Subjects
biology ,010405 organic chemistry ,Stereochemistry ,In silico ,Organic Chemistry ,Infrared spectroscopy ,010402 general chemistry ,biology.organism_classification ,Ibuprofen ,01 natural sciences ,0104 chemical sciences ,Analytical Chemistry ,Inorganic Chemistry ,chemistry.chemical_compound ,chemistry ,In vivo ,Molecular descriptor ,medicine ,Binding site ,Zebrafish ,Spectroscopy ,Derivative (chemistry) ,medicine.drug - Abstract
In this work, an ibuprofen derivative 2-(4-isobutylphenyl) -N'-phenylpropanohydrazide (ACPHZN) was synthesized and characterized by NMR, ATR-FTIR, FT-Raman, and UV-Vis spectroscopy, while their structural and spectroscopic properties were investigated using DFT calculations. In vivo study using animal model in an adult Zebrafish (Danio rerio), and molecular docking was performed. In addition, molecular descriptors of the properties of absorption, distribution, metabolism and excretion, and toxicity (ADMET) were obtained. The data calculated for ibuprofen derivative are in accordance with the experimental values. From the assays in adult zebrafish, it was found that the ibuprofen derivative was non-toxic and exhibited analgesic properties through the TRPA1, TRPV1 and TRPM8 channels. Molecular docking revealed six interactions of ACPHZN with residues of the capsaicin binding site, and a more favorable affinity energy (-9.0 kcal / mol). ADMET studies suggest that ACPHZN has a pharmacological principle as an oral drug based on a longer half-life in the human body.
- Published
- 2021