Synthesis, structural and spectroscopic analysis, and antiproliferative activity of chalcone derivate (E)-1-(4-aminophenyl)-3-(benzo[b]thiophen-2-yl)prop‑2-en-1-one in Trypanosoma cruzi

•Structural and spectroscopic characterization of a chalcone.•NMR, FT-IR, and UV–Vis spectra were analyzed by DFT calculations.•Conformational analysis, and in vitro and in silico study were carried out.•The chalcone is more active on the trypomastigote form.•The chalcone has LC50 value very smalles...

Full description

Saved in:

Bibliographic Details
Published in:	Journal of molecular structure Vol. 1253; p. 132197
Main Authors:	de Brito, Débora H. Almeida, Almeida-Neto, Francisco W.Q., Ribeiro, Lyanna R., Magalhães, Emanuel P., de Menezes, Ramon R.P.P. Bezerra, Sampaio, Tiago L., Martins, Alice M.C., Bandeira, Paulo N., Marinho, Márcia M., Marinho, Emmanuel S., Barreto, Antônio C.H., de Lima-Neto, Pedro, Saraiva, Gilberto D., Canuto, Kirley M., dos Santos, Hélcio S., Teixeira, Alexandre M.R., Ricardo, Nágila M.P. Silva
Format:	Journal Article
Language:	English
Published:	Elsevier B.V 05-04-2022
Subjects:	Chagas′ disease DFT FT-IR Molecular docking NMR UV-Vis FT-IR UV-Vis NMR DFT Molecular docking Chagas′ disease
Online Access:	Get full text
Tags:	Add Tag No Tags, Be the first to tag this record!

Description
Summary:	•Structural and spectroscopic characterization of a chalcone.•NMR, FT-IR, and UV–Vis spectra were analyzed by DFT calculations.•Conformational analysis, and in vitro and in silico study were carried out.•The chalcone is more active on the trypomastigote form.•The chalcone has LC50 value very smallest than the LC50 value of the benznidazole. There is an urgent need for new inhibitors against T. cruzi, a protozoal infection that affects about 8 million people annually around the world. In this study, we describe the synthesis, characterization, and the inhibitory effects of the chalcone (E)-1-(4-aminophenyl)-3-(benzo[b]thiophen-2-yl)prop‑2-en-1-one (BNZTHP) against T. cruzi Y strain forms. The molecular structure of this compound was characterized by spectroscopic techniques, and its potential against T. cruzi was evaluated by in vitro assays and in silico analysis. The structural data analyses allowed drawing the molecular structure of the BNZTHP chalcone. Computational quantum chemical calculations provided the normal modes of vibrations, the global chemical reactivity parameters, the most probable regions for electrophilic and nucleophilic reactive attacks, and the singlet states for BNZTHP chalcone. Regarding the activity against T. cruzi the compound exhibited more active on trypomastigote than epimastigote forms with lower toxic on LLC-MK2 host cells. Furthermore, it presented a more powerful inhibitory effect than benznidazole. From the molecular docking studies showed that trypomastigote forms were able to interact with the cruzain, trypanothione reductase, and TcGAPDH enzymes, indicating good affinity toward the active pocket. These results bring attention to the BNZTHP chalcone as candidate for the development of new option for the treatment of Chagas disease. [Display omitted]
ISSN:	0022-2860 1872-8014
DOI:	10.1016/j.molstruc.2021.132197