Molecular Design of Environment-Friendly PAE Derivatives Based on 3D-QSAR Assisted with a Comprehensive Evaluation Method Combining Toxicity and Estrogen Activities

Li, Qing; Qiu, Youli; Liu, Yu

doi:10.1007/s11270-020-04574-2

Cited by 9 publications

(5 citation statements)

References 26 publications

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“…Most PAEs are used as plasticizers in the processing of polyvinyl chloride (PVC) [ 27 ]. Referring to Li et al [ 27 ], 17 kinds of PAEs from PVC plastics were selected as representatives, which consist of higher molecular weight molecules and lower molecular weight molecules, long side-chain molecules and short side-chain molecules, different structural molecules including ring, linear chain or branched chain. The flammability property of 17 kinds of PAEs was characterized by LOI.…”

Section: Methodsmentioning

confidence: 99%

“…For example, Vahabi et al [ 25 , 26 ] defined a simple universal dimensionless index for the first time, known as the flame retardancy index (FRI), which was useful for the comparative evaluation of the flame retardancy performance of thermoplastic systems regardless of the types of polymers and additives used. Li et al [ 27 ] evaluated molecules’ multi-effect comprehensively via a simplified formula method and standard deviation score method. In this paper, dimensionless processed activity data of the flammability, biological (fish) toxicity and enrichment effects of 17 PAEs were evaluated via mathematical methods (ideal point method), which further combined to calculate the multi-effect comprehensive evaluation values of 17 PAEs.…”

Section: Introductionmentioning

confidence: 99%

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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: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

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 model employed partial least squares (PLS) regression to establish a quantitative relationship between the three-dimensional structural features of FQ molecules and their degradation capabilities in advanced oxidation processes, followed by a validation of the model’s soundness [ 25 ]. The procedure involved the following steps: First, the leave-one-out (LOO) method was employed for cross-validation of the training set molecules to obtain the cross-validation coefficient q 2 (greater than 0.5) and the optimal number of principal components N. Next, non-cross-validation regression analysis was performed to secure the non-cross-validation coefficient r 2 (greater than 0.9), the standard error of estimation (SEE), and the test statistic F [ 26 ]. Finally, the test set underwent cross-validation to determine r 2 pred (greater than 0.6).…”

Section: Methodsmentioning

confidence: 99%

Identification and Mechanistic Analysis of Toxic Degradation Products in the Advanced Oxidation Pathways of Fluoroquinolone Antibiotics

Sun,

Wang,

et al. 2024

Toxics

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The degradation of fluoroquinolones (FQs) via advanced oxidation processes (AOPs) is a promising avenue, yet the complete mineralization of certain FQ molecules remains elusive, raising concerns about the formation of toxic by-products. This study delineates five primary AOP degradation pathways for 16 commercially available FQ molecules, inferred from existing literature. Density functional theory (DFT) was employed to calculate the bond dissociation energies within these pathways to elucidate the correlation between bond strength and molecular architecture. Subsequently, Comparative Molecular Similarity Index Analysis (CoMSIA) models were constructed for various degradation reactions, including piperazine ring cleavage, defluorination, hydroxylation, and piperazine ring hydroxylation. Three-dimensional contour maps generated from these models provide a deeper understanding of the interplay between FQ molecular structure and bond dissociation energy. Furthermore, toxicity predictions for 16 FQ molecules and their advanced oxidation intermediates, conducted using VEGA 1.2.3 software, indicate that degradation products from pathways P2 and P5 pose a heightened health risk relative to their parent compounds. Furthermore, the application of the Multwfn program to compute the Fukui function for FQ molecules discerns the disparity in degradation propensities, highlighting that N atoms with higher f0 values can augment the likelihood of piperazine ring cleavage. HOMO-LUMO distribution diagrams further confirm that methoxy substitution at the 1-position leads to a dilution of HOMOs on the piperazine ring and an increased energy gap for free radical reactions, diminishing the reactivity with hydroxyl radicals. This study elucidates the pivotal role of structural characteristics in FQ antibiotics for their degradation efficiency within AOPs and unveils the underlying mechanisms of bond dissociation energy disparities. The toxicity parameter predictions for FQ molecules and their intermediates offer unique perspectives and theoretical underpinnings for mitigating the use of high-risk FQs and for devising targeted degradation strategies to circumvent the generation of toxic intermediates in AOPs through molecular structure optimization.

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“…In the Minimize module, we selected the Powell conjugate gradient method and the Tripos molecular force field (max iterations: 10,000; min energy change: 0.005 kcal/mol) and loaded the Gasteiger-Huckel charge. The lowest energy conformations of the PAE molecules were obtained [36]. The training set: test set ratio was set at 3:1 [15], and from the 28 PAE molecules, 21 PAE molecules were randomly selected as the training set, 7 PAE molecules were chosen as the test set, and diisopentyl phthalate (DIPP) molecules were used as the template molecules.…”

Section: Construction Of the 3d-qsar Model For Comprehensive Effects ...mentioning

confidence: 99%

Molecular Design and Mechanism Analysis of Phthalic Acid Ester Substitutes: Improved Biodegradability in Processes of Sewage Treatment and Soil Remediation

Sun

Zuo

et al. 2022

Toxics

Self Cite

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Phthalic acid esters (PAEs) have the characteristics of environmental persistence. Therefore, improving the biodegradability of PAEs is the key to reducing the extent of ecological harm realized. Firstly, the scoring function values of PAEs docking with various degrading enzymes in sewage treatment were calculated. Based on this, a 3D-quantitative structure-activity relationship (3D-QSAR) model for PAE biodegradability was built, and 38 PAE substitutes were created. By predicting the endocrine-disrupting toxicity and functions of PAE substitutes, two types of PAE substitutes that are easily degraded by microorganisms, have low toxicity, and remain functional were successfully screened. Meanwhile, the differences in the mechanism of molecular degradation difference before and after PAE modification were analyzed based on the distribution characteristics of amino acid residues in the molecular docking complex. Finally, the photodegradability and microbial degradability of the PAE substitutes in the soil environment was evaluated. From the 3D-QSAR model design perspective, the modification mechanism of PAE substitutes suitable for sewage treatment and soil environment degradation was analyzed. We aim to improve the biodegradability of PAEs at the source and provide theoretical support for alleviating the environmental hazards of using PAEs.

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Molecular Design of Environment-Friendly PAE Derivatives Based on 3D-QSAR Assisted with a Comprehensive Evaluation Method Combining Toxicity and Estrogen Activities

Cited by 9 publications

References 26 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

Identification and Mechanistic Analysis of Toxic Degradation Products in the Advanced Oxidation Pathways of Fluoroquinolone Antibiotics

Molecular Design and Mechanism Analysis of Phthalic Acid Ester Substitutes: Improved Biodegradability in Processes of Sewage Treatment and Soil Remediation

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