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FOOD CHEMISTRY · 2024 · IF 8.5

Effect of 4-methylbenzoquinone concentration on its covalent conjugates with β-lactoglobulin: Structural and functional properties

Jinshun Ye,Xiaotong Li,Zhenzhao Weng,Yuting Li,Xiaozhen Liu,Xiangying Yu,Fengyuan Liu,Jingkun Yan,Lin Li

This study examined the effect of quinone concentration on covalent interaction between β-lactoglobulin (β-Lg) and 4-methylbenzoquinone (4MBQ). β-Lg-4MBQ-0.2, β-Lg-4MBQ-0.4, and β-Lg-4MBQ-0.8 were prepared at 1:2, 1:1, and 2:1 M ratio of 4MBQ to β-Lg thiols, respectively. β-Lg-4MBQ-0.8 had the highest polyphenol content (19.04 ± 0.17 mg/g) and the lowest free sulfhydryl (17.12 ± 0.18 μmol/g) and amino group (181.28 ± 5.37 μmol/g) contents. Compared to β-Lg, β-Lg-4MBQ conjugates showed reduced α-helix (0.82–1.26 %) and increased β-sheet (1.17–1.50 %) content. β-Lg-4MBQ-0.8 and β-Lg-4MBQ-0.4 exhibited higher surface hydrophobicity and emulsifying properties than β-Lg-4MBQ-0.2 and β-Lg. Antioxidant activity (DPPH and ABTS scavenging) followed: β-Lg-4MBQ-0.8 (46.75 ± 0.17 % and 50.97 ± 0.51 %) > β-Lg-4MBQ-0.4 (39.50 ± 0.27 % and 46.63 ± 0.59 %) > β-Lg-4MBQ-0.2 (33.35 ± 0.71 % and 43.00 ± 0.39 %) > β-Lg (31.50 ± 0.56 % and 36.25 ± 0.90 %). β-Carotene emulsions stabilized by β-Lg-4MBQ-0.4 exhibited the highest stability. These findings provide insights into developing antioxidant emulsifiers.

CAS / MDL: 7235-40-7 452-86-8
研究领域: 食品科学 · 生物化学
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MOLECULES · 2024 ·Vol. 29 ·期 12 ·2856 · IF 4.2

A ng/L Level LC-MS Method Using Membrane SPE as Sampling Technology: Determination of Nine Halobenzoquinones in Potable Water

Qin Huang,Hua Zhou,Xianglun Wu,Jiaqi Jiang,Bingdong Zhan,Pinggu Wu

A promising method was established for the determination of nine halobenzoquinones (HBQs) in potable water by membrane solid-phase extraction (MSPE) pretreatment and the liquid chromatography–mass spectrometry (LC-MS) method. A 500 mL water sample was taken for enrichment by the SDB-RPS membrane, which was previously activated by methanol and ultrapure water. The sample was eluted with methanol and re-dissolved with the initial mobile phase after nitrogen blowing. Then, it was detected in negative ion mode using the working curve, and HBQs were quantified by the external standard method. The linearity was satisfactory in the concentration range of 4-1000 ng/L, with correlation coefficients of 0.9963~0.9994. The recoveries were 73.5~126.6% at three spiked levels, with relative standard deviations (RSDs) of 6.8~15.5%. The limits of detection (LOD, S/N = 3) values were 0.1~0.7 ng/L. The results demonstrate that the MSPE-LC-MS method is reliable, rapid, and sensitive for the simultaneous analysis of nine HBPs in potable water.

CAS / MDL: 64-18-6 34819-78-8
研究领域: 分析化学 · 环境科学
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JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY · 2020 ·Vol. 31 ·期 1 ·25-32 · IF 1.399

Determination of Catechol and Hydroquinone by Using Perilla frutescens Activated Carbon Modified Glassy Carbon Electrode

Meiqin,Zhu Jingjing,Fan Rongrong,Wang Yujie,Lv Zhaojun,Han Yongming,Peng Jun,Zheng Xinyu,Lin Ruiyu

High specific surface area activated carbon prepared by Perilla frutescens (PFHSAAC) was modified on the surface of the glassy carbon electrode (GCE) by drop-coating method to construct a PFHSAAC/GCE. The electrochemical properties of the modified electrode were investigated in detail by some electrochemical methods such as cyclic voltammetry (CV), differential pulse voltammetry (DPV) and electrochemical impedance spectroscopy (EIS). Experiment results show that the modified electrode has excellent redox activity and distinction capability toward the two isomers of catechol (CC) and hydroquinone (HQ). The separation of oxidation peak potential for HQ and CC of DPV is 112.8 mV. Under the optimal conditions, the oxidation peak currents of HQ and CC show good linear relationships with their concentrations in the ranges of 1.0 × 10-6-2.0 × 10-4 and 1.0 × 10-6-1.5 × 10-4 mol L-1, respectively. The limits of detection for HQ and CC are 3.57 × 10-7 and 4.23 × 10-7 mol L-1, respectively. The PFHSAAC/GCE exhibits good stability, repeatability and sensitivity. The developed method was used to determine HQ and CC in water samples with best results.

CAS / MDL: 123-31-9
研究领域: 分析化学 · 环境科学
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ANALYTICA CHIMICA ACTA · 2018 · IF 5.123

Conjugated polymer nanoparticles-based fluorescent biosensor for ultrasensitive detection of hydroquinone

Yuan Liu,Yu-Min Wang,Wu-Yang Zhu,Chong-Hua Zhang,Hao Tang,Jian-Hui Jiang

This work describes a simple and sensitive fluorescent method for detection of hydroquinone utilizing conjugated polymer nanoparticles (CPNs). The CPNs serve both as a catalyst to accelerate the conversion of hydroquinone to benzoquinone and a fluorescent probe . In the presence of hydroquinone, the fluorescence of CPNs can be effectively quenched by benzoquinone. The detection limit of hydroquinone was down to 5 nM and excellent selectivity toward possible interferences was obtained. This method was successfully applied for hydroquinone detection in lake water and satisfactory results were achieved.

CAS / MDL: 65-85-0
研究领域: 分析化学 · 环境科学 · 生物传感技术
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2021 · IF 4.098

Sensitive detection of glutathione through inhibiting quenching of copper nanoclusters fluorescence

Lan Li,Meiling Fu,Deyuan Yang,Yifeng Tu,Jilin Yan

A method for a sensitive fluorescence detection of glutathione was established. Glutathione-stabilized copper nanoclusters (CuNCs) were synthesized via a facile process. These CuNCs showed blue fluorescence with a peak around 450 nm. In the presence of p-benzoquinone (PBQ), the electron transfer from the copper nanoclusters to PBQ quenched the fluorescence of the CuNCs. Glutathione (GSH), as a reducing agent, formed a complex with PBQ. This formation inhibited the quenching from PBQ, and a restored fluorescence was obtained. This interaction provided a fluorescence enhancement for the measurement of GSH. Under the optimal condition, linear responses were obtained toward GSH in the ranges of 0.06–6.0 μM, with a limit of detection at 20 nM. This developed assay was easy in operation with high sensitivity and selectivity. The applicability was approved with successful glutathione measurements in real samples.

CAS / MDL: 70-18-8
研究领域: 分析化学 · 纳米技术 · 生物医学工程
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JOURNAL OF ORGANIC CHEMISTRY · 2023 · IF 3.6

Magnesium-Mediated Umpolung Carboxylation of p-Quinone Methides with CO2

Yunying Yan,Jianjun Hao,Fenfen Xie,Fen Han,Linhai Jing,Pan Han

Magnesium-mediated reductive carboxylation of p-QMs with CO2 via an Umpolung strategy has been developed, which can be used for the preparation of various aryl acetic acids. This protocol featured high atom economy, mild conditions, and operational simplicity. The creation of this Umpolung carboxylation of p-QMs will unprecedentedly extend the application of p-QMs to nucleophilic reagents.

研究领域: 有机化学 · 环境化学
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ANALYST · 2016 ·Vol. 141 ·期 15 ·4772-4781 · IF 4.033

Photoelectrocatalytic analysis and electrocatalytic determination of hydroquinone by using a Cu2O–reduced graphene oxide nanocomposite modified rotating ring-disk electrode

Hong Xie,Kaiyue Duan,Muyin Xue,Yongling Du,Chunming Wang

Reduced graphene oxide (rGO)-based Cu2O nanocomposites were prepared by a facile one-pot reaction process. The surface morphology, structure and chemical composition of Cu2O–rGO nanocomposites were characterized by transmission electron microscopy, X-ray photoelectron spectroscopy and X-ray diffraction. The Cu2O–rGO modified Pt rotating ring-disk electrode (RRDE) was successfully fabricated for the photoelectrocatalytic analysis of hydroquinone (HQ). The photoelectrochemical behaviors of HQ were investigated by the hydrodynamic differential pulse voltammetry technique, using the Cu2O–rGO modified Pt RRDE as the working electrode. The effects of pH values, rotation rates, illumination time and applied bias potential have been discussed. The possible electroactive intermediate product, namely hydroxyhydroquinone, was obtained through the photoelectrocatalytic degradation of HQ on the Cu2O–rGO modified Pt disk electrode, which was compulsively transported and could only be detected at the bare Pt ring electrode at around +0.02 V with an oxidation signal. We found that the peak current at +0.02 V had a good linear relationship with the HQ concentration in the range from 5.0 × 10−6 to 1.0 × 10−3 M, with a low limit of detection and excellent reproducibility. The present work has demonstrated that Cu2O–rGO nanocomposites have enhanced photoelectrocatalytic ability for the degradation of organic pollutants and this modified RRDE technique can be potentially applied for the in situ determination of organic pollutants.

研究领域: 环境科学 · 分析化学
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TOXICOLOGY · 2016 · IF 3.817

Tetrachlorobenzoquinone induces Nrf2 activation via rapid Bach1 nuclear export/ubiquitination and JNK-P62 signaling

Chuanyang Su,Qiong Shi,Xiufang Song,Juanli Fu,Zixuan Liu,Yawen Wang,Yuxin Wang,Xiaomin Xia,Erqun Song,Yang Song

Our previous studies demonstrated that tetrachlorobenzoquinone (TCBQ), an active metabolite of pentachlorophenol, has effects on the generation of reactive oxygen species (ROS) and oxidative stress in vitro and in vivo . Nuclear factor erythroid-derived 2-like 2 (Nrf2) is a cellular sensor of electrophilic or oxidative stress that regulates the expression of antioxidant enzymes and defensive proteins. We have illustrated that TCBQ activates Nrf2 signaling by promoting the formation of the Kelch-like ECH-associated protein 1 (Keap1) cross-linking dimer and the formation of an ubiquitination switch from Nrf2 to Keap1. The activation of Nrf2 by TCBQ may serve as an adaptive response to a TCBQ-induced oxidative insult. BTB and CNC homolog 1 (Bach1) compete with Nrf2, leading to the negative regulation of the antioxidant response element (ARE). In this report, we propose that TCBQ induces the dynamic inactivation of Bach1. We observed a rapid nuclear efflux of Bach1 and an accumulation of Nrf2 in nuclei upon TCBQ treatment that precedes the binding of Nrf2 with ARE. We found that the nuclear export of Bach1 is dependent on its chromosomal region maintenance 1 (Crm1) interaction and tyrosine phosphorylation. Although TCBQ induces the ubiquitination of Bach1, TCBQ also increases the mRNA and protein levels of Bach1, returning Bach1 to normal levels. Moreover, we found that TCBQ-induced activation of Nrf2 involves c-Jun N-terminal kinase (JNK)-P62 signaling.

CAS / MDL: 118-75-2
研究领域: 分子生物学 · 细胞信号传导 · 毒理学 · 氧化应激
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Energy & Environmental Science · 2024 · IF 32.4

Non-conjugated linkage enabling a quinone-based cathode material with long cycle life and high energy density for aqueous zinc batteries

Lu Lin,Zhiqing Xue,Tong Qiu,Jiaqi Zhu,Guoli Zhang,Hongtu Zhan,Kuo Wang,Xiaoqi Sun

Small-molecule quinones are promising cathode materials for aqueous zinc batteries with high theoretical capacity and desirable voltage. However, they usually exhibit high solubility in aqueous electrolytes, resulting in the loss of active material and a short cycle life. An efficient solution is to introduce linkages for benzoquinones (BQs) to enlarge molecular size; nevertheless, at the same time this adds dead weight, and the usually extended conjugation leads to the decreased redox potential of carbonyl groups. Herein, we present a phenyl cross-linked tri-p-benzoquinone (Ph-tri-BQ) cathode material for aqueous zinc batteries. Its solubility is greatly reduced to below 0.002% of the solubility for BQ. Besides, the weak electron-donation property and weight of the phenyl linkage are further shared by three BQs. Therefore, Ph-tri-BQ achieves a high capacity of 402 mA h g−1 with a 1.03 V discharge voltage plateau at 0.2 A g−1. Upon a 500 times increase in current density to 100 A g−1, the cathode still retains 221 mA h g−1 capacity at 0.91 V discharge voltage together with an ultra-long lifespan of 150 000 cycles. The energy storage mechanism is identified as the redox reactions on carbonyl sites with Zn2+/H+ co-storage.

CAS / MDL: 107099-99-0 626-39-1
研究领域: 材料科学 · 电化学 · 能源存储
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CHEMICAL RESEARCH IN TOXICOLOGY · 2024 · IF 3.7

Chlorobenzoquinones Aggravate RSL3-Induced Ferroptosis in ROS-Dependent Manner

Xiuhao Yu,Shaokun Chen,Hailin Wang

Chlorobenzoquinones (CBQs) are a class of emerging water disinfection byproducts that pose significant risks to public health. In this study, we found that three CBQs (tetrachloro-1,4-benzoquinone, 2,5-dichloro-1,4-benzoquinone, and 2-chloro-1,4-benzoquinone) can significantly aggravate cell death caused by Ras-selective lethal small molecule 3 (RSL3). Further study showed that the cell death caused by CBQs, either alone or in combination with RSL3, was related to iron accumulation and GPX4 inactivation, suggesting the occurrence of ferroptosis. Furthermore, reactive oxygen species are found to play a potential key role in mediating the toxicity of CBQs in CBQs and RSL3-induced ferroptosis. These findings will be helpful in understanding the toxic mechanism of CBQs to mammalian cells.

CAS / MDL: 118-75-2
研究领域: 毒理学 · 细胞生物学 · 环境科学 · 公共卫生
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ENVIRONMENT INTERNATIONAL · 2024 · IF 10.3

Metabolite identification of emerging disinfection byproduct dibromo-benzoquinone in vivo and in vitro: Multi-strategy mass-spectrometry annotation and toxicity characterization

Meijiao Zhou,Yichao Qian,Mine Du,Jun Wang,Jinhua Li,Wei Wang

Halobenzoquinones (HBQs) are emerging disinfection byproducts (DBPs) of high toxicity and also are shared active toxic intermediates of multiple halogenated organic pollutants. Due to the strong oxidizing property and electrophilicity, HBQs exhibit extremely diverse metabolism pathways in organisms. The identification of toxic-decisive metabolites is pivotal, albeit challenging, for understanding the toxicity mechanisms of HBQs. We employed dibromo-benzoquinone (DBBQ) as a representative HBQ, and established a systematic analytical strategy using high-resolution mass spectrometry, which collectively coupled suspect screening (SS), mass defect filtering (MDF), product ion filtering (PIF), isotopic signature filtering (ISF), and molecular networking (MN). As a result, 20 biotransformation products of DBBQ were identified in vivo and in vitro , involving metabolism reactions such as hydroxylation, methylation, methoxylation, acetylation, sulfonation, glucuronidation, glutathionylation, dimerization, and conjugation with amino acids or fatty acids. Quantitative structure-activity relationship (QSAR) analysis and cytotoxicity experiments consistently demonstrated the significantly high toxicity of the fatty acid conjugate compared to the parent compound DBBQ and other metabolites, pinpointing the important role of the fatty acid conjugation in determining the metabolism and toxicity of HBQs. The research conducted a comprehensive evaluation of the metabolism of a typical HBQ with the combination of multiple analytical and toxicity characterization methods, therefore screen out the most important metabolism pathway of HBQs.

CAS / MDL: 64-18-6
研究领域: 环境科学 · 毒理学 · 分析化学
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JOURNAL OF POWER SOURCES · 2019 · IF 7.467

Synthesis of 1,4-benzoquinone dimer as a high-capacity (501 mA h g−1) and high-energy-density (>1000 Wh kg−1) organic cathode for organic Li-Ion full batteries

Zeyi Yao,Wu Tang,Xinxin Wang,Chuan Wang,Chuluo Yang,Cong Fan

The organic cathodes with high specific capacity are highly desirable to fabricate high-specific-energy-density organic Li-ion full cells. Herein, we initially propose the long-term plan for the systematic synthesis of the oligomer family of 1,4-benzoquinone (BQ), which can possess theoretical specific capacity above 500 mA h g −1 . As a start, the dimer of 1,4-benzoquinone (2,2′-bis-(1,4-benzoquinone), BBQ) is synthesized, which can realize the specific capacity of 501 mA h g −1 and the average discharge potential of ~2.5 V (vs. Li + /Li). Even facing the dissolution problem, BBQ can deliver average specific capacities of ~190 mA h g −1 during 3000 cycles at 500 mA g −1 and ~120 mA h g −1 during 8000 cycles at 2 A g −1 in Li-ion half cells. Afterwards, the all-organic Li-ion full cells are fabricated by using the reduced state (Li 4 TP) of lithium terephthalate (Li 2 TP) as the starting anode and BBQ as the starting cathode. Delightfully, the resulting Li 4 TP-BBQ Li-ion full cells can realize the specific capacity of 316 mA h g −1 cathode in the 1st cycle (500 mA g −1 ). Meanwhile, average specific capacities of ~98 mA h g −1 during 1000 cycles can be fulfilled (500 mA g −1 ). The results of the Li 4 TP-BBQ Li-ion full cells are among the best all-organic Li-ion full batteries reported to date.

研究领域: 材料科学 · 电化学 · 能源存储
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