Trypanocidal potential of synthetic p-aminochalcones: In silico and in vitro evaluation

Dutra Barroso Gomes, Naiara; Paula Magalhães, Emanuel; Rodrigues Ribeiro, Lyanna; Cavalcante, John Washington; Morais Gomes Maia, Marcelo; Cunha da Silva, Felipe Ramon; Ali, Arif; Machado Marinho, Márcia; Silva Marinho, Emmanuel; Silva dos Santos, Hélcio; Costa Martins, Alice Maria; Róseo Paula Pessoa Bezerra de Menezes, Ramon

doi:10.1016/j.bioorg.2023.106931

Bioorganic Chemistry

2023

DOI: 10.1016/j.bioorg.2023.106931

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Trypanocidal potential of synthetic p-aminochalcones: In silico and in vitro evaluation

Naiara Dutra Barroso Gomes,

Emanuel Paula Magalhães,

Lyanna Rodrigues Ribeiro

et al.

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2024

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Cited by 2 publications

References 81 publications

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Effect of Cinnamaldehyde Chalcone on Behavior in Adult Zebrafish (Danio rerio): In Silico Approach

Carneiro Romão,

Costa Siqueira,

Amâncio Ferreira

et al. 2024

Chemistry & Biodiversity

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The study focuses on the anxiolytic potential of chalcone (2E,4E)‐1‐(2‐hydroxyphenyl)‐5‐phenylpenta‐2,4‐dien‐1‐one (CHALCNM) in adult zebrafish. Successfully synthesized in 58% yield, CHALCNM demonstrated no toxicity after 96 h of exposure. In behavioral tests, CHALCNM (40 mg/kg) reduced locomotor activity and promoted less anxious behavior in zebrafish, confirmed by increased permanence in the light zone of the aquarium. Flumazenil reversed its anxiolytic effect, indicating interaction with GABAA receptors. Furthermore, CHALCNM (4 and 20 mg/kg) preserved zebrafish memory in inhibitory avoidance tests. Virtual screening and ADMET profile studies suggest high oral bioavailability, access to the CNS, favored by low topological polarity (TPSA ≤ 75 Å²) and low incidence of hepatotoxicity, standing out as a promising pharmacological agent against the GABAergic system. In molecular coupling, CHALCNM demonstrated superior affinity to diazepam for the GABAA receptor. These results reinforce the therapeutic potential of CHALCNM in the treatment of anxiety, highlighting its possible future clinical application.

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Effect of Cinnamaldehyde Chalcone on Behavior in Adult Zebrafish (Danio rerio): In Silico Approach

Carneiro Romão,

Costa Siqueira,

Amâncio Ferreira

et al. 2024

Chemistry & Biodiversity

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Easy Synthesis and In Vitro Evaluation of Halogenated Chalcones against Trypanosoma cruzi

Avila-Sorrosa,

Laurel-Gochicoa,

Vargas-Díaz

et al. 2024

Chemistry

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Chalcones are organic structures that occur naturally in flavonoids and isoflavonoids from diverse vegetables and fruits. Their properties have promising applications in medicinal chemistry as antiparasitic agents against malaria, leishmaniasis, and Chagas disease. Parasitic diseases, a global health challenge, affect thousands of people around the world. The lack of access to affordable treatments causes many deaths, especially in developing countries. Chagas disease, a neglected infection whose etiological agent is the protozoan Trypanosoma cruzi (T. cruzi), is currently incurable without timely treatment and depends on two primary nitrated chemotherapeutic agents: Nifurtimox (Nfx) and Benznidazole (Bzn). However, these drugs exhibit low selectivity and serious adverse effects, accentuating the critical need to develop new, safer chemotherapeutic options. In this context, herein we report the synthesis of halogen chalcone derivatives by an affordable and sustainable method. In vitro studies against T. cruzi demonstrated that the fluorine-containing structures have the best bioactive profile with inhibitions comparable to Nfx and Bzn. Additionally, ADME analysis was performed to determine the crucial physicochemical and pharmacokinetic descriptors of the series of compounds, which were shown to be suitable for enteral absorption and have a low risk of crossing the blood–brain barrier and damaging brain tissue.

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Trypanocidal potential of synthetic p-aminochalcones: In silico and in vitro evaluation

Cited by 2 publications

References 81 publications

Effect of Cinnamaldehyde Chalcone on Behavior in Adult Zebrafish (Danio rerio): In Silico Approach

Effect of Cinnamaldehyde Chalcone on Behavior in Adult Zebrafish (Danio rerio): In Silico Approach

Easy Synthesis and In Vitro Evaluation of Halogenated Chalcones against Trypanosoma cruzi

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