Combined QSAR/QSPR, Molecular Docking, and Molecular Dynamics Study of Environmentally Friendly PBDEs with Improved Insulating Properties

Sicheng, Liu; Sun, Shijun

doi:10.1007/s40242-019-8353-9

Cited by 10 publications

(4 citation statements)

References 25 publications

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“…As per the results in Table 3 , the optimal principal component n of PAEs’ multi-effect CoMSIA model was 10, while the cross-validation coefficient q 2 was 0.616 (generally considered that when the value of q 2 > 0.5, the model has the credible predictive ability [ 38 , 39 ]). The non-cross-validation coefficient r 2 was 1.000 (>0.9), SEE was 0.008, and F was 507.314, indicating the greater fitting ability and robustness of the model [ 40 , 41 ]. The external test coefficient r 2 pred was 0.66 (>0.6), and SEP of the test set was 0.16, which specified the model also had well predictive ability [ 42 , 43 ] and the constructed CoMSIA model met the requirements [ 44 ].…”

Section: Resultsmentioning

confidence: 99%

A Modified 3D-QSAR Model Based on Ideal Point Method and Its Application in the Molecular Modification of Plasticizers with Flame Retardancy and Eco-Friendliness

Zhang

Zhao

2020

Polymers

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The addition of plasticizers makes plastics flammable, and thus, poses a potential risk to the environment. In previous researches, plasticizers with flame retardancy had been synthesized, but their eco-friendliness had not been tested or described. Thus, in this paper, eco-friendliness plasticizers with flame retardancy were designed based on phthalic acid esters (PAEs), which are known as common plasticizers and major plastic additives. For a comprehensive analysis, such as flammability, biotoxicity, and enrichment effects, 17 PAEs’ comprehensive evaluation values were calculated based on the ideal point method. Further, a multi-effect three-dimensional quantitative structure-activity relationship (3D-QSAR) model of PAEs’ flammability, biotoxicity and enrichment effects was constructed. Thus, 18 dimethyl phthalate (DMP) derivatives and 20 diallyl phthalate (DAP) derivatives were designed based on three-dimensional contour maps. Through evaluation of eco-friendliness and flammability, six eco-friendly PAE derivatives with flame retardancy were screened out. Based on contour maps analysis, it was confirmed that the introduction of large groups and hydrophobic groups was beneficial to the simultaneous improvement of PAEs’ comprehensive effects, and multiple effects. In addition, the group properties were correlated significantly with improved degrees of the comprehensive effects of corresponding PAE derivatives, confirming the feasibility of the comprehensive evaluation method and modified scheme.

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Section: Resultsmentioning

confidence: 99%

A Modified 3D-QSAR Model Based on Ideal Point Method and Its Application in the Molecular Modification of Plasticizers with Flame Retardancy and Eco-Friendliness

Zhang

Zhao

2020

Polymers

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“…The optimal principal component (n) of the comprehensive effect CoMSIA model is 6, and the cross-validation coefficient (q 2 ) is 0.747 (>0.5) ( Table 3 ), indicating that the prediction ability of the developed model has a certain degree of credibility. The non-cross validation coefficient (R 2 ) is 0.929 (>0.9), the standard deviation (SEE) is 0.100, and the F value is 26.209, indicating that the model exhibits good fitting ability and robustness [ 37 , 38 ]. The model has certain reliability and universality in the prediction of the PAEs’ comprehensive effect value with insulation, toxicity, and bioconcentration.…”

Section: Resultsmentioning

confidence: 99%

PAEs Derivatives’ Design for Insulation: Integrated In-Silico Methods, Functional Assessment and Environmentally Friendly Molecular Modification

Zhang

Zhao

2022

IJERPH

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As a common substance in production and life, phthalic acid esters (PAEs), the main component of plastics, have brought more and more serious problems to the environment. This study normalized the insulation, toxicity, and bioconcentration data of 13 PAEs to eliminate the dimensional coefficients of each index, and then used the comprehensive index method to calculate the comprehensive effect value of PAEs with three properties. The comprehensive effect value was used as the data source to construct the 3D-QSAR model of PAE molecular comprehensive effect. The DAP was selected as the target molecule, the distribution of each force field in the three-dimensional equipotential map was analyzed, and 30 molecular modification schemes were created. The constructed single-effect models of insulation, toxicity, and bioconcentration of PAEs and the scoring function module of DS software were used to evaluate the stability and environmental friendliness of PAE derivative molecules. Four PAE derivatives were screened for increased comprehensive effects, enhanced insulation, and reduced toxicity and bioconcentration. By calculating the binding energy of the target molecule and the derivative molecule with the degrading enzyme under different applied electric fields, it was found that the binding energy of DAP-1-NO2-2-CH2C6H5 decreases more than DAP does when there is an applied electric field, indicating that the degradation ability of degrading enzymes on PAE derivative molecules is reduced, which indirectly proves that the insulation is enhanced. The innovation of this paper lies in the insulation, toxicity, and bioenrichment data of PAEs being processed by mathematical method for the first time, and PAEs with high insulation, low toxicity, and low bioconcentration were designed by building a comprehensive model.

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“…Other performance metrices evaluated were the standard error of estimate and Fischer's value which were 0.067 and 192.02 and 0.015 and 1528.55 for CoMFA and CoMSIA1 models respectively. Furthermore, the non-cross validation coefficients were all greater than 0.90, indicating strong adaptability and robustness of the developed models [31,32]. The correlation between the predicted value and the actual value of training set and test set r2 were 0.9896 and 0.9997 in CoMFA (Figure 3F), and correlation between the predicted value and the actual value of training set and test set r2 were 0.9996 and 0.9997 in CoMSIA1, indicating that the model had good predictive ability.…”

Section: Ld 50 3d-qsarmentioning

confidence: 92%

Effects of Phthalate Esters (PAEs) on Cell Viability and Nrf2 of HepG2 and 3D-QSAR Studies

Liu

Huang

Xiao

et al. 2021

Toxics

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Phthalate esters (PAEs) are a widespread environmental pollutant, and their ecological and environmental health risks have gradually attracted attention. To reveal the toxicity characteristics of these compounds, ten PAEs were selected as research objects to establish a cell model. CCK-8 was used to determine cell viability, Western blots were used to determine the content of Nrf2 in HepG2, and the LD50 collected for the 13 PAEs administered to rats. On this basis, 3D-QSAR models of IC50, LD50 and Nrf2 were established. The experimental results showed that as the time of PAEs exposure increased (24, 48 and 72 h), cell viability gradually decreased. The test concentration (62.5 /125/250 μM) of PAEs exposed for 48 h could significantly increase the content of Nrf2, and the 1000 μM PAEs could inhibit the content of Nrf2. The model is relatively stable and predicts well that the introduction of large and hydrophobic groups may significantly affect the toxic effects of PAEs on cells. The present study provided a potential tool for predicting the LD50 and Nrf2 of new PAEs, and provide a reference for the design of new less toxic PAEs in the future.

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Combined QSAR/QSPR, Molecular Docking, and Molecular Dynamics Study of Environmentally Friendly PBDEs with Improved Insulating Properties

Cited by 10 publications

References 25 publications

A Modified 3D-QSAR Model Based on Ideal Point Method and Its Application in the Molecular Modification of Plasticizers with Flame Retardancy and Eco-Friendliness

A Modified 3D-QSAR Model Based on Ideal Point Method and Its Application in the Molecular Modification of Plasticizers with Flame Retardancy and Eco-Friendliness

PAEs Derivatives’ Design for Insulation: Integrated In-Silico Methods, Functional Assessment and Environmentally Friendly Molecular Modification

Effects of Phthalate Esters (PAEs) on Cell Viability and Nrf2 of HepG2 and 3D-QSAR Studies

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