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TPhP
ENVIRONMENTAL POLLUTION · 2019 · IF 5.714

Enhanced degradation of triphenyl phosphate (TPHP) in bioelectrochemical systems: Kinetics, pathway and degradation mechanisms

Rui Hou,Xiaoshan Luo,Chuangchuang Liu,Lihua Zhou,Junlin Wen,Yong Yuan

Triphenyl phosphate (TPHP) is one of the major organophosphate esters (OPEs) with increasing consumption. Considering its largely distribution and high toxicity in aquatic environment, it is important to explore an efficient treatment for TPHP. This study aimed to investigate the accelerated degradation of TPHP in a three-electrode single chamber bioelectrochemical system (BES). Significant increase of degradation efficiency of TPHP in the BES was observed compared with open circuit and abiotic controls. The one-order degradation rates of TPHP (1.5 mg L −1 ) were increased with elevating sodium acetate concentrations and showed the highest value (0.054 ± 0.010 h −1 ) in 1.0 g L −1 of sodium acetate. This result indicated bacterial metabolism of TPHP was enhanced by the application of micro-electrical field and addition acetate as co-substrates. TPHP could be degraded into diphenyl phosphate (DPHP), hydroxyl triphenyl phosphate (OH-TPHP) and three byproducts. DPHP was the most accumulated degradation product in BES, which accounted more than 35.5% of the initial TPHP. The composition of bacterial community in BES electrode was affected by the acclimation by TPHP, with the most dominant bacteria of Azospirillum , Petrimonas , Pseudomonas and Geobacter at the genera level. Moreover, it was found that the acute toxic effect of TPHP to Vibrio fischeri was largely removed after the treatment, which revealed that BES is a promising technology to remove TPHP threaten in aquatic environment.

研究领域: 环境工程 · 生物技术 · 微生物学 · 水处理
✓ 已验证 DOI PubMed 高影响因子
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ENVIRONMENT INTERNATIONAL · 2024 · IF 10.3

Rap1 and mTOR signaling pathways drive opposing immunotoxic effects of structurally similar aryl-OPFRs, TPHP and TOCP

Bilin Zhao,Shuang Zheng,Gaoxiang Yang,Zhijun He,Jiewei Deng,Lijuan Luo,Xinyan Li,Tiangang Luan

Aryl organophosphorus flame retardants (aryl-OPFRs), commonly used product additives with close ties to daily life, have been regrettably characterized by multiple well-defined toxicity risks. Triphenyl phosphate (TPHP) and tri-o-cresyl phosphate (TOCP), two structurally similar aryl-OPFRs, were observed in our previous study to exhibit contrasting immunotoxic effects on THP-1 macrophages, yet the underlying mechanisms remain unclear. This study sought to address the knowledge gap by integrating transcriptomic and metabolomic analyses to elucidate the intricate mechanisms. During individual omics analyses, we unfortunately only obtained highly similar results for both TPHP and TOCP, failing to identify the key reasons for their differences. These results revealed comparable disturbances induced by both compounds, including disruptions in nucleic acid synthesis and energy metabolism, blocking ADP to ATP conversion by reducing TCA cycle intermediates, consequently leading to ATP depletion. However, through integrative analysis, specific pathways affected by each compound were successfully identified, shedding light on their unique effects. TPHP reduced GTP levels necessary for Rap1 activation, thereby inhibiting phagocytosis and adhesion of THP-1 macrophages. Conversely, TOCP stimulated the mTOR signaling pathway, enhancing phosphorylation of downstream proteins S6K, RHOA, and PKC, consequently promoting immune responses. This study not only clarified the distinct immunotoxic mechanisms of TPHP and TOCP but also provided critical insights into how structural variations in aryl-OPFRs can lead to markedly different immune responses, thereby informing future risk assessments and regulatory strategies for these compounds.

CAS / MDL: 67-63-0 67-56-1
研究领域: 毒理学 · 免疫学 · 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 · 2022 · IF 16.744

Complexation and reduction of soil iron minerals by natural polyphenols enhance persulfate activation for the remediation of triphenyl phosphate (TPHP)-contaminated soil

Xiaona Dong,Ruonan Feng,Xiaoxue Yang,Yuanming Jiang,Lulu Chen,Liwei Chen,Canlan Jiang,Tianming Cai

Peroxydisulfate-based in-situ chemical oxidation (PDS-ISCO) is a promising technology for soil remediation. The weak potential of soil constituents for PDS decomposition results in the low degradation efficiency of soil contaminants. Herein, we propose a new soil remediation strategy by accelerating the activation efficiency of PDS using chelating and reducing reagents (CRs) to complex and reduce soil Fe-minerals. Experimental results demonstrated that the introduction of tea polyphenols (TP) into soil-PDS system could effectively improve the reduction of Fe-minerals and the degradation of triphenyl phosphate (TPHP) in soil. With increasing TP concentration from 0 to 40 mM, the degradation efficiency of TPHP increased from 10.8% to 58.6% in an upland soil (T1 soil). TP could directly complex and reduce the solid-phase Fe-minerals, leading to a significant increase of Fe(II) content, especially the insoluble Fe(II) content, which could further induce the PDS activation. Results of radical quenching experiments, electron paramagnetic resonance (EPR) analysis, and kinetic solvent isotope effect (KSIE) evaluation showed that sulfate radicals (SO 4 •− , especially surface-bound SO 4 •− ), hydroxyl radicals (HO•, especially surface-bound HO•), and singlet oxygen ( 1 O 2 ) played major roles in TPHP degradation, with the estimated contributions of 39.03%, 43.99%, and 16.98%, respectively. The higher content of high active Fe fractions, such as amorphous Fe, the larger yields of Fe(II) species and TPHP degradation. Increased content of soil organic matter (SOM) and pH value from 2.5 to 8.0 may reduce TPHP degradation. The effects of inorganic anions and Mn-minerals, presented in natural soil, on TPHP degradation were very limited. Simulated in-situ soil remediation using soil column confirmed that this strategy is suitable for the large-scale remediation of contaminated soil.

研究领域: 环境科学 · 土壤化学 · 污染控制 · 化学工程
✓ 已验证 DOI 高影响因子
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ENVIRONMENTAL POLLUTION · 2026 · IF 7.2

Structural Analogs TOCP and TPHP Induce Immunotoxicity in Zebrafish through Divergent Disruption of Energy Metabolism

Xinyan Li,Dongmei Lai,Yao Yao,Jiewei Deng,Lijuan Luo,Xiaoping Liang,Tiangang Luan

Aryl organophosphate flame retardants (aryl-OPFRs), such as triphenyl phosphate (TPHP) and tris(2-methylphenyl) phosphate (TOCP), have been identified as ubiquitous environmental contaminants, but their immunotoxicity and underlying mechanisms in aquatic organisms remain largely unclear. This study investigated the immunomodulatory effects of two structurally analogous aryl-OPFRs using zebrafish larvae during the window of exclusively innate immunity, prior to the maturation of the adaptive immune system. Strikingly, they induced opposite immune responses: TOCP increased macrophage numbers and provoked inflammation, whereas TPHP decreased neutrophil and macrophage counts and suppressed inflammation. This divergence challenges the conventional structure-activity relationship paradigm. Both compounds ultimately compromised antibacterial capacity. To elucidate the mechanism, integrated transcriptomic and metabolomic analyses were performed, revealing that the opposing phenotypes were linked to differential regulation of energy-related pathways, including glycolysis and purine metabolism. Molecular docking predicted AMPK as a potential common target, while subsequent molecular dynamics simulations provided a critical dynamic perspective: TPHP rapidly dissociated from AMPK, whereas TOCP maintained a more persistent interaction. This differential binding stability offers a plausible mechanistic basis for their distinct immunometabolic reprogramming. Overall, these findings demonstrate that the structural analogs TOCP and TPHP induce divergent immunotoxicity in zebrafish, potentially mediated through a differential disruption of host energy metabolism during the early innate immune phase.

CAS / MDL: 1173020-30-8
✓ 已验证 产品关联 DOI PubMed 高影响因子
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SCIENCE OF THE TOTAL ENVIRONMENT · 2019 · IF 5.589

Degradation of triphenyl phosphate (TPhP) by CoFe2O4-activated peroxymonosulfate oxidation process: Kinetics, pathways, and mechanisms

Qingyun Song,Yiping Feng,Zhu Wang,Guoguang Liu,Wenying Lv

The aryl organophosphate flame retardant triphenyl phosphate (TPhP) has been frequently detected in environment and biota, and the potential risks of TPhP to aquatic organisms have also been demonstrated. The degradation of TPhP by CoFe 2 O 4 activated peroxymonosulfate (PMS) was studied in this work. At initial pH of 7.0, 10 μM TPhP could be removed by 99.5% with 0.25 g/L CoFe 2 O 4 and 0.5 mM PMS after 6 min oxidation, indicating the excellent performance of CoFe 2 O 4 activated PMS process on the treatment of TPhP. The influence of PMS and CoFe 2 O 4 dosage, initial pH, humic acid (HA), and anions (Cl − , NO 3 − , and HCO 3 − ) on TPhP degradation were investigated systematically. Results showed that the degradation of TPhP was enhanced with increasing PMS concentrations from 0.1 to 1 mM, while it reduced as CoFe 2 O 4 dosage increased. TPhP degradation efficiencies depended on solution pH with neutral pH showing the optimum degradation conditions. Recycling experiment indicated that the CoFe 2 O 4 nanoparticles (NPs) possessed high potential for reusability. The radical identification experiments were performed and SO 4 • − was confirmed as the dominant radicals in TPhP degradation, and activation mechanism of PMS by CoFe 2 O 4 NPs was hence explained. Humic acids (HA) (2–20 mg/L) as the representative organic natural matter existing in environment inhibited TPhP removal. Anions including Cl − , NO 3 − , and HCO 3 – all reduced TPhP degradation. In addition, TPhP degradation products were identified by liquid chromatography-mass spectrometry, and the degradation pathways of TPhP were proposed accordingly.

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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ENVIRONMENTAL SCIENCE & TECHNOLOGY · 2025 · IF 11.3

Opposing Visual Impairments Induced by Structurally Similar Organophosphate Flame Retardants TPHP and CDP in Zebrafish Larvae

Yiqun Song,Ting Xu,Hongchang Zhang,Shuangqing Hu,Sheng Wei,Miao Cao,Huan Wang,Daqiang Yin

Vision is the primary sensory function for most animals and is also a sensitive toxic target of environmental pollutants. A new class of organophosphate flame retardants (OPFRs) termed emerging OPFRs (eOPFRs) with limited toxicological information is rapidly developed into the substitutes of traditional OPFRs. In this study, we investigated the visual toxicity of triphenyl phosphate (TPHP, one traditional OPFR) and cresyl diphenyl phosphate (CDP, one emerging OPFR) on zebrafish larvae at environmentally relevant concentrations (3 and 30 nM). After 5 days of exposure, an opposite toxicity was found between the two OPFRs, manifested in the light perception and the gene expressions of visual opsins. CDP caused a weak reaction to light and overall inhibition of opsin expression (0.7- to 0.8-fold) in the larvae, while TPHP tended to stimulate these events (1.2- to 2.4-fold). Besides, we identified a key transcription factor, tbx2a, that was significantly disrupted in both OPFRs’ exposure. The differing ways in which both OPFRs bind to Tbx2a may be the reason behind their opposite effects. These findings provided new clues for the toxicological mechanisms of OPFRs and revisited the question regarding safe substitutes for those emerging contaminants.

CAS / MDL: 115-86-6 26444-49-5
研究领域: 环境毒理学 · 发育生物学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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CHEMOSPHERE · 2022 · IF 8.943

Efficient removal of organophosphate esters by ligand functionalized MIL-101 (Fe): Modulated adsorption and DFT calculations

Sheng Fan,Xinru Lu,Haoliang Li,Xiaodong Du,Xiaoyu Huang,Yao Ma,Juan Wang,Xueqin Tao,Zhi Dang,Guining Lu

Organophosphate esters (OPEs) are a new class of flame retardants present in diverse waters. The study focused on the removal of aqueous OPEs using functionalized MIL-101(Fe), which was a representative of the metal-organic frameworks (MOFs). Adsorption kinetics of tris(2-chloroethyl) phosphate (TCEP), tributyl phosphate (TnBP), and triphenyl phosphate (TPhP) were investigated. Additionally, TCEP was selected as the model contaminant to study the adsorption isotherms, thermodynamics, and effect of solution matrix properties. Adsorption mechanisms obtained from the experiments were confirmed using density functional theory (DFT) calculations. Adsorption kinetics indicated that functionalized MOFs provided a significant enhancement to the removal of TCEP. The maximum adsorption capacities q m of MIL-101(Fe), MIL-101(Fe)–NH 2 , MIL-101(Fe)–OH, and MIL-101(Fe)–CH 3 at 298 K for TCEP were 76.040, 282.940, 119.680, and 181.274 μmol/g, respectively. By comparing the adsorption behavior of functionalized MOFs, MIL-101(Fe)–NH 2 was proved to be most efficient for TCEP removal . Based on the adsorption experiments and DFT calculations, TCEP removal was dominated by physical adsorption. The van der Waals (vdW) interactions and hydrogen bonding were assumed to be involved in the adsorption. This work proves that appropriate ligand functionalization is promising for the removal of aqueous OPEs, which also provides a new insight for the control of OPEs pollution.

研究领域: 环境科学 · 材料科学 · 化学工程
✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF HAZARDOUS MATERIALS · 2022 · IF 14.224

Triphenyl phosphate induced reproductive toxicity through the JNK signaling pathway in Caenorhabditis elegans

Chongli Shi,Chen Wang,Lingjun Zeng,Yi Peng,Yeyong Li,Haibin Hao,Yang Zheng,Chao Chen,Haibo Chen,Jin Zhang,Minghui Xiang,Yuan Huang,Hui Li

Triphenyl phosphate (TPHP) is a widely used aryl organophosphate flame retardant (OPFR) that has attracted attention due to its frequent detection in the environment and living organisms. To date, the reproductive toxicity of TPHP has been investigated in organisms, but its molecular mechanisms are not fully understood. Caenorhabditis elegans ( C. elegans ) is the ideal animal for the study of reproductive toxicity following environmental pollutants, with short generation times, intact reproductive structures, and hermaphroditic fertilization. This study aimed to explore the reproductive dysfunction and molecular mechanisms induced by TPHP exposure in C. elegans . Specifically, exposure to TPHP resulted in a reduction in the number of eggs laid and developing embryos in utero, an increase in the number of apoptotic gonadal cells, and germ cell cycle arrest. The JNK signaling pathway is a potential pathway inducing reproductive toxicity following TPHP exposure based on transcriptome sequencing (RNA-seq). Moreover, TPHP exposure induced down-regulation of vhp-1 and kgb-2 gene transcription levels, and the knockout of vhp-1 and kgb-2 in the mutant strains exhibited more severe toxicity in apoptotic gonad cells, embryos, and eggs developing in utero, suggesting that vhp-1 and kgb-2 genes play a crucial role in TPHP-induced reproductive toxicity. Our data provide convergent evidence showing that TPHP exposure results in reproductive dysfunction through the JNK signaling pathway and improve our understanding of the ecotoxicity and toxicological mechanisms of aryl-OPFRs.

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