Bioactive conformation analysis of anthranilic diamide insecticides: DFT-based potential energy surface scanning and 3D-QSAR investigations

Jiang, Danping; Zhu, Chengchun; Shao, Xusheng; Cheng, Jiagao; Li, Zhong

doi:10.1016/j.cclet.2015.04.010

Cited by 10 publications

(5 citation statements)

References 31 publications

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“…According to the frontier molecular orbital theory, the HOMO and LUMO are the two most important factors that influence the bioactivities of compounds. The HOMO energy is associated with the ionization potential, and the LUMO energy is related to electron affinity ( Jiang et al, 2015 ). The higher HOMO energy tends to preferentially donate electrons in the first place, and the lower LUMO energy indicates that the molecule has the priority to accept electrons.…”

Section: Resultsmentioning

confidence: 99%

“…The higher HOMO energy tends to preferentially donate electrons in the first place, and the lower LUMO energy indicates that the molecule has the priority to accept electrons. Moreover, a lower energy gap (ΔE) between HOMO and LUMO usually means that the molecule has better insecticidal or fungicidal activity ( Jiang et al, 2015 ). As shown in Figure 4 , the positive molecular orbitals were symbolized with blue, and the negative molecular orbitals were symbolized with green for both the HOMO and LUMO.…”

Section: Resultsmentioning

confidence: 99%

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Design, synthesis, and insecticidal activity of a novel series of flupyrimin analogs bearing 1-aryl-1H-pyrazol-4-yl subunits

Zhao

Tang²,

Huang³

et al. 2022

Front. Chem.

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To discover new potential insecticides to protect agricultural crops from damage, a series of novel flupyrimin derivatives containing an arylpyrazole core were designed and synthesized. Their structures were confirmed by 1H NMR, 13C NMR, and HRMS. Bioassays indicated that the 31 compounds synthesized possessed excellent insecticidal activity against Plutella xylostella. Among these target compounds, the lethality of A3, B1-B6, D4, and D6 reached 100% at 400 μg/ml. Moreover, when the concentration dropped to 25 μg/ml, the insecticidal activities against the Plutella xylostella for compounds B2, B3, and B4 still reached more than 70%. The structure–activity relationship of the Plutella xylostella was discussed. The density functional theory analysis of flupyrimin and B4 was carried out to support the abovementioned structure–activity relationship. The possible binding modes between receptor and active groups in title compounds were also verified by docking simulation. These results provided new ideas for the development of these novel candidate insecticides in the future.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Design, synthesis, and insecticidal activity of a novel series of flupyrimin analogs bearing 1-aryl-1H-pyrazol-4-yl subunits

Zhao

Tang²,

Huang³

et al. 2022

Front. Chem.

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“…The potential energy surface of nano SiO 2 is scanned using Gaussian 16 software under the conditions of maintaining different distances from cations [ 39 ]. The changes in the relative positions of the cations can result in an increase or decrease in the energy of the surface of nano SiO 2 , and the resulting effects on the conformation of nano SiO 2 particles can be monitored.…”

Section: Simulation Methods Of Density Functional Theorymentioning

confidence: 99%

Study on the Effect of Cations on the Surface Energy of Nano-SiO2 Particles for Oil/Gas Exploration and Development Based on the Density Functional Theory

Ni,

Zhang,

Wang

et al. 2024

Molecules

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Although nano SiO2 exhibits excellent application potential in the field of oil and gas exploration and development, such as drilling fluid, enhanced oil/gas recovery, etc., it is prone to agglomeration and loses its effectiveness due to the action of cations in saline environments of oil and gas reservoirs. Therefore, it is crucial to study the mechanism of the change in energy between nano SiO2 and cations for its industrial application. In this paper, the effect of cations (Na+, K+, Ca2+, and Mg2+) on the surface energy of nano SiO2 particles is investigated from the perspective of molecular motion and electronic change by density functional theory. The results are as follows: Due to the electrostatic interactions, cations can migrate towards the surface of nano SiO2 particles. During the migration process, monovalent cations are almost unaffected by water molecules, and they can be directly adsorbed on the surface by nano SiO2 particles. However, when divalent cations migrate from a distance to the surface of nano SiO2 particles, they can combine with water molecules to create an energy barrier, which can prevent them from moving forward. When divalent cations break through the energy barrier, the electronic kinetic energy between them and nano SiO2 particles changes more strongly, and the electrons carried by them are more likely to break through the edge of the atomic nucleus and undergo charge exchange with nano SiO2 particles. The change in interaction energy is more intense, which can further disrupt the configuration stability of nano SiO2. The interaction energy between cations and nano SiO2 particles mainly comes from electrostatic energy, followed by Van der Waals energy. From the degree of influence of four cations on nano SiO2 particles, the order from small to large is as follows: K+ < Na+ < Mg2+ < Ca2+. The research results can provide a theoretical understanding of the interaction between nano SiO2 particles and cations during the application of nano SiO2 in the field of oil and gas exploration and development.

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“…The quality of the models was heavily dependent on an accurate representation of the bioactive conformations of the ligands, a specific conformation adapted to ligand−receptor interactions, which provided guidance on the design of new bioactive molecules. 29 However, the insect RyRs remained unresolved in their full structures because of their large size, integral membrane protein nature, and dynamic properties. The only protein−ligand complex currently available was a chlorantraniliprole complex with a mammalian RyR1 (PDB code: 6M2W), which led to a difficulty in understanding the true bioactive conformation of lead compounds in insect RyRs.…”

Section: ■ Introductionmentioning

confidence: 99%

“…frugiperda. − A three-dimensional quantitative structure–activity relationship (3D-QSAR) analysis was used to study the structure–insecticidal activity of compounds against agricultural pests to further improve the insecticidal activity of these lead compounds. The quality of the models was heavily dependent on an accurate representation of the bioactive conformations of the ligands, a specific conformation adapted to ligand–receptor interactions, which provided guidance on the design of new bioactive molecules . However, the insect RyRs remained unresolved in their full structures because of their large size, integral membrane protein nature, and dynamic properties.…”

Section: Introductionmentioning

confidence: 99%

3D-QSAR Combination with Molecular Dynamics Simulations to Effectively Design the Active Ryanodine Receptor Agonists against Spodoptera frugiperda

Yu,

Huang,

Cheng

et al. 2023

J. Agric. Food Chem.

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Computer-aided molecular modeling was applied to design a series of Spodoptera frugiperda RyR agonists. Comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) were used to generate 3D-QSAR models. MD simulations in the complex with S. frugiperda native, mutant RyR, and mammalian RyR1 under physiological conditions were used to validate the detailed binding mechanism. Binding free energy calculation by molecular mechanics generalized surface area (MM-GBSA) explained the role of key amino acid residues in ligand–receptor binding. Therefore, 14 new compounds were effectively designed and synthesized, and a bioassay indicated that compounds A-2 and A-3 showed comparable activity to that of chloranthraniliprole with LC50 values of 0.27, 0.18, and 0.20 mg L–1, respectively, against S. frugiperda. Most target compounds also displayed good activity against Mythinma separata at 0.1 mg L–1. Molecular docking and MM-GBSA calculations demonstrated that A-3 had a better binding capacity with native and mutant S. frugiperda RyRs.

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Bioactive conformation analysis of anthranilic diamide insecticides: DFT-based potential energy surface scanning and 3D-QSAR investigations

Cited by 10 publications

References 31 publications

Design, synthesis, and insecticidal activity of a novel series of flupyrimin analogs bearing 1-aryl-1H-pyrazol-4-yl subunits

Design, synthesis, and insecticidal activity of a novel series of flupyrimin analogs bearing 1-aryl-1H-pyrazol-4-yl subunits

Study on the Effect of Cations on the Surface Energy of Nano-SiO2 Particles for Oil/Gas Exploration and Development Based on the Density Functional Theory

3D-QSAR Combination with Molecular Dynamics Simulations to Effectively Design the Active Ryanodine Receptor Agonists against Spodoptera frugiperda

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