Environmental Conversion Path Inference of New Designed Fluoroquinolones and Their Potential Environmental Risk

Zhang, Wenhui; Sun, Ruihao; Zhao, Xiaohui; Liu, Yu

doi:10.1007/s00244-019-00672-3

Cited by 6 publications

(2 citation statements)

References 50 publications

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“…Zhang et al reported using molecular metabolic stability and genotoxicity as indices for the functional evaluation of FQs derivatives [106]. Both Zhang et al and Hou et al reported using the HQSAR model for the genotoxicity of quinolones toward Salmonella typhimurium for predicting the negative logarithm lowest observed effect concentration (pLOEC) values, which were then used for characterizing bacterial genotoxicity [59,107].…”

Section: Evaluation Of the Functional Properties Of Nor Derivativesmentioning

confidence: 99%

Strategies to Control Human Health Risks Arising from Antibiotics in the Environment: Molecular Modification of QNs for Enhanced Plant–Microbial Synergistic Degradation

Sun

Zhao

2021

IJERPH

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In the present work, a comprehensive screening and evaluation system was established to improve the plant–microbial synergistic degradation effects of QNs. The study included the construction of a 3D-QSAR model, the molecular modification, environmental friendliness and functional evaluation of drugs, degradation pathway simulation, and human health risk assessment. Molecular dynamics was applied to quantify the binding capacity of QNs toward the plant degradation enzyme (peroxidase) and microbial degradation enzymes (manganese peroxidase, lignin peroxidase, and laccase). The fuzzy comprehensive evaluation method was used in combination with the weighted average method for normalization and assigning equal weights to the plant and microbial degradation effect values of the QNs. Considering the synergistic degradation effect value as the dependent variable and the molecular information of the QNs as the independent variable, a 3D-QSAR model was constructed for the plant–microbial synergistic degradation effect of QNs. The constructed model was then employed to conduct the molecular modification, environmental friendliness and functional evaluation, degradation pathway simulation, and human health risk assessment of transformation products using pharmacokinetics and toxicokinetics. The results revealed that the synergistic degradation effect 3D-QSAR (CoMSIA) model exhibited good internal and external prediction ability, fitting ability, stability, and no overfitting phenomenon. Norfloxacin (NOR) was used as the target molecule in the molecular modification. A total of 35 NOR derivatives with enhanced plant–microbial synergistic degradation effect (1.32–21.51%) were designed by introducing small-volume, strongly electronegative, and hydrophobic hydrogen bond receptor groups into the active group of the norfloxacin structure. The environment-friendliness and the functionality of NOR were evaluated prior to and after the modification, which revealed seven environment-friendly FQs derivatives exhibiting moderate improvement in stability and bactericidal efficacy. The simulation of the NOR plant and microbial degradation pathways prior to and after the modification and the calculation of the reaction energy barrier revealed Pathway A (D-17 to D-17-2) and Pathway B (D-17 to D-17-4) as the most prone degradation pathways in plants and Pathway A (D-17 to D-17-1) and Pathway B (D-17 to D-17-4) as the most prone degradation pathways in microorganisms. This demonstrated that the degradation of the modified NOR derivatives was significantly enhanced, with the hydroxylation and piperazine ring substitution reaction playing an important role in the degradation process. Finally, the parameters, including hepatotoxicity, mutagenicity, and rodent carcinogenicity, among others, predicted using the pharmacokinetics and toxicokinetics analyses revealed a significant reduction in the human health risk associated with the modified NOR, along with a considerable reduction in the toxicity of its transformation products, implying that the human health risk associated with the transformation products was reduced remarkably. The present study provides a theoretical basis for novel ideas and evaluation programs for improving the plant–microbial synergistic degradation of the QNs antibiotics for source control and drug design, thereby reducing the residues of these antibiotics and the associated hazard in the complex plant–soil environment, ultimately decreasing the potential risks to human health.

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Section: Evaluation Of the Functional Properties Of Nor Derivativesmentioning

confidence: 99%

Strategies to Control Human Health Risks Arising from Antibiotics in the Environment: Molecular Modification of QNs for Enhanced Plant–Microbial Synergistic Degradation

Sun

Zhao

2021

IJERPH

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“…To evaluate the potential risks of novel fluoroquinolone derivatives, Zhang et al (2020) used an established hologram quantitative structure–activity relationship model to study the genotoxicity of these derivatives following natural or artificial transformation processes, such as biological metabolism (Zhao et al 2018a), photodegradation (Zhao et al 2018b), microbial degradation (Wetzstein et al 1998), and chlorination disinfection (Yin 2012). Although both phthalates and fluoroquinolones are common new pollutants in the water environment, due to their differences in properties there are some differences between the environmental transformation paths of phthalates and fluoroquinolones.…”

Section: Introductionmentioning

confidence: 99%

Investigation of the Potential Environmental Risks of Phthalate Derivatives Designed To Be Environmentally Friendly

Zhang

Sun

Hou

et al. 2020

Enviro Toxic and Chemistry

Self Cite

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Phthalate derivatives with low estrogenic activity, high infrared spectrum signals, high Raman characteristic vibration spectrum, high fluorescence intensity, and high ultraviolet sensitivity were selected as precursors from our previous studies, so that the changes in their toxicity and estrogenic activity during biological metabolism, ozone oxidation, photocatalytic degradation, photodegradation, and microbial degradation could be studied.The transformation pathways of these derivatives were simulated, and the reaction energy barriers were calculated. To determine the potential environmental risks of these phthalate derivatives, the pharmacophore models of biotoxicity and estrogen activity of phthalates were used to predict the biotoxicity and estrogen activity of the transformed products. The results showed an increase in the biotoxicity and estrogen activity of the biometabolites, ozonation products, photocatalytic degradation products, and microbial degradation products; the only products that did not follow this trend were the photodegradation products. Notably, the pathways that produced more potentially toxic compounds were the less favorable paths. Our results indicate that the transformation products of the designed environmentally friendly phthalate derivatives potentially pose environmental risks. To avoid such risks, the environmental transformation pathway of these derivatives should be simulated to screen for environmentally friendly phthalate molecules. Environ Toxicol Chem 2020;39:1138–1148. © 2020 SETAC

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QuEChERS Approach for the Analysis of Three Fluoroquinolone Antibiotics in Wastewater: Concentration Profiles and Ecological Risk in Two Nigerian Hospital Wastewater Treatment Plants

Ajibola

Amoniyan

Ekoja

et al. 2020

Arch Environ Contam Toxicol

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Environmental Conversion Path Inference of New Designed Fluoroquinolones and Their Potential Environmental Risk

Cited by 6 publications

References 50 publications

Strategies to Control Human Health Risks Arising from Antibiotics in the Environment: Molecular Modification of QNs for Enhanced Plant–Microbial Synergistic Degradation

Strategies to Control Human Health Risks Arising from Antibiotics in the Environment: Molecular Modification of QNs for Enhanced Plant–Microbial Synergistic Degradation

Investigation of the Potential Environmental Risks of Phthalate Derivatives Designed To Be Environmentally Friendly

QuEChERS Approach for the Analysis of Three Fluoroquinolone Antibiotics in Wastewater: Concentration Profiles and Ecological Risk in Two Nigerian Hospital Wastewater Treatment Plants

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