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CHEMOSPHERE · 2017 · IF 4.208

Spectroscopic and molecular modeling approaches to investigate the interaction of bisphenol A, bisphenol F and their diglycidyl ethers with PPARα

Jie Zhang,Tiehua Zhang,Tianzhu Guan,Ping Ruan,Dayong Ren,Weichang Dai,Hansong Yu,Tiezhu Li

A fluorescence polarization (FP) assay for the simultaneous determination of bisphenol A (BPA), bisphenol F (BPF), bisphenol A diglycidyl ether (BADGE) and bisphenol F diglycidyl ether (BFDGE) was developed. The method was based on the competition between bisphenols (BPs) and fluorescein-labeled dexamethasone derivative (Dex-fl) for mouse peroxisome proliferator-activated receptor α ligand binding domain (mPPARα-LBD). A recombinant soluble protein derivative mPPARα-LBD* was prepared, then in vitro binding of 4 BPs to mPPARα-LBD* was investigated. Fluorescence polarization assay showed that these compounds exhibited different binding potencies with mPPARα-LBD*. Additionally, molecular dynamics simulations were performed to further understand the mechanism of BPs binding affinity for mPPARα-LBD*. Docking results elucidated that the driving forces for the binding of BPs to mPPARα-LBD* were predominantly dependent on hydrophobic and hydrogen-bonding interactions. Comparison of the calculated binding energies vs. experimental binding affinities yielded a good correlation (R 2  = 0.7258). The proposed method has potential for multi-residue detection of BPA, BPF, BADGE, and BFDGE.

研究领域: 生物化学 · 环境科学 · 毒理学
✓ 已验证 DOI PubMed 高影响因子
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ENVIRONMENTAL POLLUTION · 2020 · IF 6.793

Deposition, depletion, and potential bioaccumulation of bisphenol F in eggs of laying hens after consumption of contaminated feed

Zhiming Xiao,Ruiguo Wang,Decheng Suo,Shi Wang,Xiaomin Li,Shujun Dong,Tong Li,Xiaoou Su

Increasing concerns over bisphenol A (BPA) as an endocrine disrupting chemical (EDC) and its adverse effects on both humans and animals have led to the substitution by structural analogs, such as bisphenol F (BPF), in many application areas. Information regarding to the carry-over of this emerging chemical in farm animals is essential for legislation and risk assessment purposes. In this study, a large-scale number of animal experiments were designed to investigate the transfer of BPF from feed to eggs. One control and three experimental groups of laying hens (72 hens per group) were fed with basal diets and BPF-contaminated feed at concentration levels of 0.1, 0.5 and 2.5 mg kg −1 , respectively, for two weeks. The hens were then fed with BPF-free diets for a further four weeks. Eggs were collected daily, and separated into egg yolk and white for BPF analysis. The effects of different levels of BPF exposure on laying performance followed a non-monotonic dose-response curve, since low level BPF (0.1 mg kg −1 ) exposure did increase the laying rate, mean egg weight and daily feed intake, while high level BPF (2.5 mg kg −1 ) exposure showed a decreasing trend. BPF residues were detected in both egg yolks and whole eggs after two days of administration, and plateau phase was achieved within 9–18 days. There are clear linear dose-response relationships between the plateau BPF concentrations in feed and eggs. The residue of BPF was found mainly in egg yolks with conjugated form and depleted slowly (still detected 21 days after feeding the BPF-free diet of the high level group). Mean carry-over rate of 0.59% BPF from feed to eggs was obtained. Compared with the carry-over rates of PCBs and dioxins, BPF showed a relatively minor trend of bioaccumulation in eggs. To the best of our knowledge, this is the first report on the deposition, depletion, and bioaccumulation study of bisphenols in farm animals. The quantity of data can therefore be helpful in the frame of risk assessment, especially for a comprehensive estimation of consumer exposure to the residues of bisphenols.

CAS / MDL: 620-92-8
研究领域: 动物科学 · 环境科学 · 食品安全
✓ 已验证 产品关联 DOI PubMed 高影响因子
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ECOTOXICOLOGY AND ENVIRONMENTAL SAFETY · 2025 · IF 6.1

The developmental toxicity of bisphenol F exposure on the zebrafish larvae

Biyu Wu,Zirui Cheng,Xiang Li,Minxing Liang,Xue Wang,Duan Pi,Jiayi Liu,Huiling Li,Jun Zhao,Junjie Wang,Fang Liang,Xuegeng Wang

As a major substitute for the bisphenol A (BPA), the use of the bisphenol F (BPF) has increased dramatically in recent years. Growing evidence suggest that BPF shares numerous toxicological properties with BPA, raising the concerns about its potential impact on the health of organisms. However, the developmental toxicity of BPF remains poorly understood. In this study, we conducted a 5-day BPF exposure experiment on zebrafish ( Danio rerio ) from blastula stage at concentrations of 2, 20, 200, and 2000 µg/L. Our results demonstrated a significant increase in hatching rates across all treatment groups at 2 days post-fertilization (dpf). The esr1 was significantly upregulated at 2000 µg/L by 5 dpf, while no significant change was observed in ar . The frequency of operculum loss significantly increased at exposure concentrations of 20, 200, and 2000 µg/L, and a notable increase in notochord loss was observed at 2000 µg/L. To explore the underlying mechanisms, transcriptomic analysis was performed to identify differentially expressed genes (DEGs). GO and KEGG pathway enrichment analysis revealed that the toxic effects of BPF were closely associated with osteoclast differentiation, the FoxO signaling pathway, and the MAPK signaling pathway. These pathways influenced critical biological processes, including response to stimuli, animal organ morphogenesis, detoxification, and biomineralization. This study provides evidence that BPF exposure at environmentally relevant concentrations (2 µg/L) is harmful to hatching, concentrations above 20 µg/L exhibit estrogenic-disrupting activity and exert toxicological effects on the development of the head skeleton in zebrafish. These effects are particularly linked to disruptions in osteoclast differentiation.

CAS / MDL: 620-92-8
研究领域: 环境毒理学 · 分子生物学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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SCIENCE OF THE TOTAL ENVIRONMENT · 2025 · IF 8

Equipotent bisphenol S and bisphenol F with widely differing modes of action exhibit additive effects in immunotoxicity: insights based on intrinsic immunity, apoptosis and regeneration, and oxidative stress

Xincong Su,Li Kai,Xiaowen Han,Rongzhi Wang,Xiao Yang,Xuedong Wang,Jin Yan,Qiuhui Qian,Zejun Wang,Huili Wang

Bisphenol S (BPS) and Bisphenol F (BPF), as alternatives to bisphenol A (BPA), are recognized for their endocrine-disrupting properties, but their combined immune toxicity mechanisms remain poorly understood. This study systematically evaluates the individual and joint immune toxicity effects of BPS and BPF through ADMET predictions, transgenic zebrafish models, and molecular docking analyses. The results indicate that equal effect concentration BPS and BPF act through distinct immune pathways: BPS primarily targets macrophages to mediate immune responses, while BPF significantly stimulates neutrophil proliferation and induces a stronger inflammatory response through chemokine signaling. Molecular docking studies show that BPF binds more stably to pro-apoptotic protein Mapk8 and oxidative stress-related protein Hsp90aa1, leading to significantly higher levels of apoptosis and reactive oxygen species (ROS) compared to BPS. The similarity of modes of action (MOA)between BPS and BPF based on relevant immune indicators calculated and experimentally is about 0.3; this quantitative result also proves that modes of action differ widely. Nonetheless, most of the indicators showed superimposed effects in the combined experiments, and it is noteworthy that the oxidative stress indicators (SOD, MDA) showed synergistic effects, suggesting that BPS and BPF, which have very different modes of action, are able to be risk assessed using an additive model with respect to immunity, but may exhibit synergistic risks with respect to oxidative stress. This research demonstrates that BPS and BPF induce immune toxicity via different molecular targets and pathways and highlights the need to account for their synergistic effects in risk assessments. These findings provide important insights into the immune toxicity mechanisms of BPA substitutes and the potential risks of combined exposures.

研究领域: 环境科学 · 毒理学 · 分子生物学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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TALANTA · 2023 · IF 6.1

Large–size porous spherical 3D covalent organic framework for preconcentration of bisphenol F in water samples and orange juice

Qiong He,Ying Chen,Yuyang Liu,Qiang Wang,Chiyang He,Shaorong Liu

Large–size spherical sorbents with particle size of 10–50 μm are widely applied in separation fields, however it is still a great challenge to synthesize such large–size spherical covalent organic framework (COF). In this work, a type of large–size porous 3D COF was size–controablly synthesized via a two–step strategy, in which a large–size porous 3D spherical polymer was prepared first through a Pickering emulsion polymerization using nano silica as the stabilizer, and subsequently it was converted into porous spherical 3D COF by a solvothermal method . The as–prepared porous spherical COF (COF–320 as a model) showed size–controllable uniform spherical morphology within 15–45 μm, large specific surface area, fine crystalline structure, and good chemical stability. When used as the sorbent for dispersive solid–phase extraction (d–SPE) of bisphenol F (BPF), the porous spherical COF–320 (15 μm) displayed high adsorption capacity ( Q max  = 335.6 mg/g), high enrichment factor (80 folds), and good reusability (at least five cycles). By coupling the d–SPE method to HPLC, a new analytical approach was developed and successfully applied to the determination of trace BPF in two water samples, an orange juice and a standard sample with recoveries of 96.0–102.2 % (RSD = 1.1–1.5 %), 95.7–97.4 % (RSD = 1.4–4.4 %) and 98.7 % (RSD = 2.3 %), respectively. The limit of detection (S/N = 3) and limit of quantification (S/N = 10) were 0.1 and 0.3 ng/mL, respectively. The new synthesis strategy opens a viable way to prepare large–size porous spherical COFs, and the developed analytical method can be potentially applied to sensitively detect the trace BPF in water samples and beverages.

CAS / MDL: 66-98-8
研究领域: 材料科学 · 分析化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES · 2023 ·Vol. 24 ·期 13 ·10898 · IF 5.6

Transcriptome Analysis of the Developmental Effects of Bisphenol F Exposure in Chinese Medaka (Oryzias sinensis)

Zhiying Liang,Yafen Guo,Duan Pi,Xiang Li,Bingying Li,Yongsi Huang,Xiaohong Song,Ramji Kumar Bhandari,Xuegeng Wang

Bisphenol F (BPF) has been used in the syntheses of polymers, which are widely used in coatings, varnishes, adhesives, and other plastics. During the past decades, BPF contamination in the aquatic environment has dramatically increased due to its release from manmade products. Concerns have driven much attention to whether it may adversely impact aquatic lives or human beings. The present study performed an acute toxic exposure experiment and a 15 d developmental exposure of BPF at environmental concentrations (20, 200, and 2000 ng/L) using Chinese medaka (Oryzias sinensis). In the acute toxic exposure, the LC50of BPF to Chinese medaka is 87.90 mg/L at 96 h. Developmental exposure induced a significant increase in the frequency of larvae with abnormalities in the 2000 ng/L BPF group compared to the control group. Transcriptomic analysis of the whole larvae revealed 565 up-regulated and 493 down-regulated genes in the 2000 ng/L BPF exposure group. Analysis of gene ontology and KEGG pathways enrichments indicated endocrine disorders to be associated with BPF-induced developmental toxicity. The present results suggest that BPF is developmentally toxic at 2000 ng/L concentration in Chinese medaka and causes endocrine-related aberrations in the transcriptional network of genes.Keywords:Bisphenol F;Chinese medaka;toxicity;developmental defects;endocrine disruptor

CAS / MDL: 620-92-8
研究领域: 环境科学 · 毒理学 · 分子生物学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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RSC Advances · 2014 ·Vol. 4 ·期 63 ·33466-33473 · IF 3.708

The efficient hydroxyalkylation of phenol with formaldehyde to bisphenol F over a thermoregulated phase-separable reaction system containing a water-soluble Brønsted acidic ionic liquid

Qing Wang,Zhi Min Wu,Yongfei Li,Ying Tan,Ning Liu,Yuejin Liu

The efficient hydroxyalkylation of phenol with formaldehyde to bisphenol F over a thermoregulated phase-separable reaction system containing a water-soluble Brønsted acidic ionic liquid was studied. The reaction system containing the water-soluble IL showed thermoregulated biphasic behavior with change of the alkyl chain length of IL, temperature and water amount. Four types of imidazolium-, ammonium-, phosphonium- and pyridinium-based water-soluble ionic liquids with different anions of dihydrogen phosphate [H2PO4]−, acetate [CH3COO]− and hydrogen sulfate [HSO4]− were used as both Brønsted acidic catalysts and thermoregulated solvents. Among them, [C6MIM][HSO4] gave a high yield of 80.5% and a selectivity of 96.9% for bisphenol F, and the optimal reaction conditions were stirring speed 450 rpm, phenol–formaldehyde ratio 6 : 1, IL catalyst molar concentration 12.5%, reaction temperature 90 °C and reaction time 1 h. [C6MIM][HSO4] could be recovered by simple decantation and could retain its original activity even after six recycling-uses [CnMIM][HSO4] with the alkyl chain length n = 6 found to be the most suitable for the synthesis of bisphenol F because of both the formation of a thermoregulated monophasic reaction system at 90 °C to enhance the reaction efficiency and as a thermoregulated phase-transition solvent to facilitate its recovery from the reaction system.

CAS / MDL: 616-47-7
研究领域: 化学工程 · 催化反应
✓ 已验证 产品关联 DOI 高影响因子
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Journal of Cleaner Production · 2024 · IF 9.7

Carbon vacancies and spatial confinement effects of VC-FCN0.3 prepared by spatial self-corrosion strategy achieved eco-friendly photocatalytic degradation to bisphenol F

Min Wang,Guanghua Lu,Runren Jiang,Tianjian Dang,Yufang Chen,Jianchao Liu,Zhenhua Yan,Jun Hou

The widespread use of bisphenol F (BPF) as the commonly used alternative to bisphenol A (BPA) in the industry and its hazardous effects on ecological system and human health have attracted widespread attention. In this study, V C -FCN 0.3 hollow nanotube structure with confinement space effects and combined carbon vacancies was constructed by the spatial self-corrosion strategy, which effectively addressed the inherent limitations of conventional carbon nitride and achieved 100% removal rate of BPF within 2 h under visible light. Carbon vacancies not only accelerated the transfer of photogenerated carriers, but also enhanced the adsorption and activation of oxygen that accelerating the production of ·O 2 − , the main active species in this system. In addition, the special spatial structure shortened the mass transfer distance between the target pollutants and the active species. What's more, V C -FCN 0.3 showed excellent, stable, and eco-friendly photocatalytic degradation of bisphenol F over a wide pH range and in five water matrices, contributing effectively to the solution of purification of wastewater containing bisphenol analogues.

CAS / MDL: 620-92-8 108-78-1
研究领域: 环境科学 · 材料科学 · 化学工程
✓ 已验证 产品关联 DOI 高影响因子
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ECOTOXICOLOGY AND ENVIRONMENTAL SAFETY · 2025 · IF 6.1

Tetramethyl bisphenol F exposure induces human ovarian granulosa cell senescence and mouse ovarian damage by regulating ESRRB signalling

Huiyu Fan,Chunming Li,Yifei Lv,Tongyun Qi,Yizhou Huang,Linjuan Ma,Yibing Lan,Peiqiong Chen,Zheng Lou,Jianhong Zhou

Tetramethyl bisphenol F (TMBPF), regarded as a promising alternative to bisphenol A (BPA) across multiple industries, is now incorporated into polymer coatings for metal cans used in food and beverage packaging. Recent research has highlighted possible health risks associated with TMBPF, yet its impact on ovarian function and the mechanisms involved remain inadequately understood. This study provides a thorough evaluation of TMBPF's effects on granulosa cells (GCs) and uncovers its transgenerational influence on female reproductive health. We exposed pregnant CD1 mice to TMBPF at doses of 50 μg/kg/day or 200 μg/kg/day from gestational day 7 (GD7) through postnatal day 21 (PND21). Our findings indicated that maternal exposure to TMBPF adversely affects the reproductive system of the F1 generation by elevating the levels of E2, FSH, and LH, reducing the ovarian index, and increasing the number of collagen fibers in the ovarian stroma. The human granulosa-like tumor cell line KGN was employed as an experimental model to assess the toxic effects of TMBPF on GCs. The findings revealed that sublethal concentrations of TMBPF induced mitochondrial dysfunction, cellular senescence, and disrupted redox homeostasis in GCs in vitro. Our transcriptome sequencing analyses indicated that ESRRB upregulation might play a critical role in TMBPF-induced cellular senescence. Additionally, TMBPF exposure induced KGN cells senescence and senescent cell accumulation in F1 mouse ovaries by promoting ESRRB/p21 signalling. Collectively, our results indicate that TMBPF disrupts hormone levels in the ovaries, accelerates GCs senescence and promotes ovarian fibrosis, adversely affecting ovarian function in offspring. This study provides new insights into the potential effects of TMBPF exposure on the reproductive system and the related mechanisms.

CAS / MDL: 8001-30-7
研究领域: 生殖生物学 · 毒理学 · 分子生物学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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CHEMICAL ENGINEERING JOURNAL · 2020 · IF 10.652

Rapid microwave synthesis of Fe3O4-PVP@ZIF-67 as highly effective peroxymonosulfate catalyst for degradation of bisphenol F and its mechanism analysis

Jianan Cui,Tingting Liu,Qian Zhang,Ting Wang,Xiaohong Hou

Various metal-based heterogeneous catalysts activated peroxymonosulfate for organic pollutants degradation are increasingly recognized as an environmentally important sewage treatment technology. In this study, polyvinyl pyrrolidone (PVP) modified Fe 3 O 4 loaded ZIF-67 magnetic catalyst with transition metal cobalt ion was prepared for the first time by microwave-assisted solvothermal (MS) method within 30 min to activate peroxymonosulfate. The microwave synthesis process changed the time-consuming shortcoming of conventional method. The catalytic activity of the synthesized Fe 3 O 4 -PVP@ZIF-67 was assessed on bisphenol F (BPF) removal. The result showed 99.8% BPF was removed under the conditions of catalyst content of 0.15 g·L −1 , PMS content of 0.3 mM, and pH without adjustment in 60 min. And the Fe 3 O 4 -PVP@ZIF-67/PMS system exhibited a quality catalytic performance when the solution pH of BPF varied from 3 to 11. Compared with humic acid (HA), inorganic anions (Cl − , H 2 PO 4 − , SO 4 2− , HCO 3 − , and CO 3 2− ) showed slight effect to the degradation system. The quenching experiment verified that the main active substance in this system was SO 4 − •. Based on the degradation intermediates identified by gas chromatography-mass spectrometer (GC–MS), the main degradation pathways were proposed for the degradation of BPF. Overall, Fe 3 O 4 -PVP@ZIF-67 as PMS activator is promising catalyst for sulfate radical-based wastewater treatment.

研究领域: 环境科学 · 化学工程 · 材料科学
✓ 已验证 DOI 高影响因子
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INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH · 2015 · IF 2.587

Hydroxyalkylation of Phenol with Formaldehyde to Bisphenol F Catalyzed by Keggin Phosphotungstic Acid Encapsulated in Metal–Organic Frameworks MIL-100(Fe or Cr) and MIL-101(Fe or Cr)

Meng Chen,Jiaqi Yan,Ying Tan,Yongfei Li,Zhimin Wu,Langsheng Pan,Yuejin Liu

Hydroxyalkylation of phenol with formaldehyde to bisphenol F was investigated over the metal–organic frameworks of MIL-100(Fe or Cr) and MIL-101(Fe or Cr) encapsulated with Keggin phosphotungstic acid (PTA). PTA@MIL-100(Fe or Cr)(β) and PTA@MIL-101(Fe or Cr)(β) with different β values (the molar ratio of W/M, where M = Fe or Cr) were prepared and characterized by XRD, BET, FT-IR, TG, SEM, TEM, and ICP. The research results showed that PTA@MIL-100(Fe or Cr)(β) had a higher catalytic activity than PTA@MIL-101(Fe or Cr)(β). PTA@MIL-100(Fe)(0.4) was the most effective among the studied catalysts and had excellent reusability. A 92.12% product yield and 93.01% selectivity for bisphenol F could be obtained over the PTA@MIL-100(Fe)(0.40) catalyst. The effects of the reaction time, reaction temperature, catalyst concentration, and phenol/formaldehyde molar ratio on the reaction performance were also investigated. A plausible mechanism for hydroxyalkylation of phenol with formaldehyde to bisphenol F was proposed.

CAS / MDL: 100-21-0 554-95-0
研究领域: 化学工程 · 催化科学
✓ 已验证 产品关联 DOI 高影响因子
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MOLECULES · 2024 ·Vol. 29 ·期 23 ·5545 · IF 4.2

Rapid Degradation of Bisphenol F Using Magnetically Separable Bimetallic Biochar Composite Activated by Peroxymonosulfate

Hui Liang,Ruijuan Li,Tongjin Liu,Rumei Li,Yuxiao Zhu,Feng Fang

Peroxymonosulfate (PMS)-based advanced oxidation processes have shown potential for the removal of organic contaminants; however, the preparation of catalysts with high degradation efficiencies and rapid reaction rates remains a challenge. In this study, we have successfully synthesized CoFe bimetallic modified corn cob-derived biochar (CoFe/BC) for the activation of PMS, achieving the rapid and efficient degradation of bisphenol F (BPF). The synthesized CoFe/BC catalyst demonstrated excellent catalytic performance, achieving over 99% removal within 3 min and exhibiting a removal rate of 90.0% after five cycles. This could be attributed to the cyclic transformation of Co and Fe, which sustained rapid PMS activation for BPF degradation, and Co0/Fe0played a significant role in the cyclic transformation. Furthermore, the electron paramagnetic resonance tests confirmed that •SO4−and •OH were the primary reactive oxygen species, while •O2−played a minor role in BPF degradation. This study highlights the high degradation efficiency, rapid reaction rate, excellent magnetic separation properties, and exceptional reusability of CoFe/BC catalysts for BPF removal, providing valuable insights for practical wastewater treatment.

研究领域: 环境科学 · 化学工程
✓ 已验证 产品关联 DOI PubMed 高影响因子
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