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<p>Semicarbazones have been used as insecticides and act through different mechanisms of action by inhibiting enzymes essential for insect metabolism, including enzymes that act on the central nervous system of insects associated with other general toxic effects for these organisms. In this context, the purpose of the study was to evaluate the toxicity of semicarbazones and their respective substituent groups using in silico toxicological modeling approach, analyzing the stability between ligand-receptor and their structure/activity relationship (SAR) to establish relationships between behavioral toxicity syndrome (BTS) in fish as a method of environmental biomonitoring. Quantum calculations were obtained using the Density Functional Theory method for electronic structural characterization. Toxicity prediction was carried out using the Ecological Structure Activity Relationship (ECOSAR) predictive model, which estimates the acute and chronic toxicity of organic compounds in aquatic organisms such as fish, aquatic invertebrates, and aquatic plants. Molecular docking simulations were conducted using the Autodock Vina software against the target acetylcholinesterase (AChE). The protein–ligand complexes with the lowest energy and RMSD of less than 2&#xa0;Å were submitted to molecular dynamics simulations. The quantum data corroborates the surface analysis of lipophilicity, which indicates that the alkenyl substituent chain has a greater partition contribution fragment in which dihalogenated derivatives increase in this proportion. The HOMO–LUMO gap (∆<i>E</i>) and log Pow properties can infer toxicity and latency induction, delineating that organic compounds with log Pow lower than 2 and <i>∆E</i> higher than 9&#xa0;eV are more susceptible to low toxicity. The S2-AChE complex showed greater stability, characterized by low conformational variations and high cohesion between the results. This stability was corroborated by the formation of hydrogen bonds with amino acid residues present in the receptor's active site.</p>

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Computational investigation of behavioral toxicity syndromes (BTS) of synthetics halosubstituted semicarbazones

  • 期刊论文

  • 发表日期：

    2025年10月17日

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  • Damião Sampaio de Sousa,
  • Victor Moreira de Oliveira,
  • Akenaton Onassis Cardoso Viana Gomes,
  • Francisco Rogênio da Silva Mendes,
  • Marcia Machado Marinho,
  • Pedro de Lima-Neto,
  • Gabrielle Silva Marinho

摘要

Semicarbazones have been used as insecticides and act through different mechanisms of action by inhibiting enzymes essential for insect metabolism, including enzymes that act on the central nervous system of insects associated with other general toxic effects for these organisms. In this context, the purpose of the study was to evaluate the toxicity of semicarbazones and their respective substituent groups using in silico toxicological modeling approach, analyzing the stability between ligand-receptor and their structure/activity relationship (SAR) to establish relationships between behavioral toxicity syndrome (BTS) in fish as a method of environmental biomonitoring. Quantum calculations were obtained using the Density Functional Theory method for electronic structural characterization. Toxicity prediction was carried out using the Ecological Structure Activity Relationship (ECOSAR) predictive model, which estimates the acute and chronic toxicity of organic compounds in aquatic organisms such as fish, aquatic invertebrates, and aquatic plants. Molecular docking simulations were conducted using the Autodock Vina software against the target acetylcholinesterase (AChE). The protein–ligand complexes with the lowest energy and RMSD of less than 2 Å were submitted to molecular dynamics simulations. The quantum data corroborates the surface analysis of lipophilicity, which indicates that the alkenyl substituent chain has a greater partition contribution fragment in which dihalogenated derivatives increase in this proportion. The HOMO–LUMO gap (∆E) and log Pow properties can infer toxicity and latency induction, delineating that organic compounds with log Pow lower than 2 and ∆E higher than 9 eV are more susceptible to low toxicity. The S2-AChE complex showed greater stability, characterized by low conformational variations and high cohesion between the results. This stability was corroborated by the formation of hydrogen bonds with amino acid residues present in the receptor's active site.