Synthesis, structural and spectroscopic characterization, in silico study, and antinociceptive effect in adult zebrafish of 2-(4-isobutylphenyl)-N'-phenylpropanohydrazide

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. (c) 2021 Elsevier B.V. All rights reserved.

Automated summary

In this study, a novel ibuprofen derivative was synthesized and characterized using various spectroscopic techniques, and its structural and spectroscopic properties were investigated through DFT calculations. In vivo experiments demonstrated that the ibuprofen derivative had analgesic properties, was non-toxic, and showed potential as an oral drug based on its pharmacokinetic properties.