Current Pharmaceutical Analysis
·
2023
·Vol. 19
·期 6
·511-520
·
IF 0.6
Zhang Mengmeng,Zou Qiaogen
Background: Atopic dermatitis (AD) is an allergic skin disease that can be inherited. Crisaborole is a specific drug developed to deal with this disease. The compounds of 4-(4- Bromo-3-formyl-phenoxy)-benzonitrile and 4-(4-(4-bromo-3-formylphenoxy)-3- formylphenoxy) benzonitrile
are the representative impurities in the synthesis of Crisaborole active pharmaceutical in gradient (API). Owing to the genotoxic impurities that could lead to cancer and gene mutations, it is necessary to develop a simple, efficient, sensitive, and accurate method to detect these impurities.
In this study, the 4-(4-Bromo-3-formyl-phenoxy)-benzonitrile and 4-(4-(4- bromo-3-formylphenoxy)-3-formylphenoxy)benzo- nitrile present in Crisaborole API were detected using UPLC-MS/MS. Methods: The separation was made on a ZORBAX Eclipse XDB-Pheny column (4.6 mm ×75mm, 3.5
μm) with the mobile phase of acetonitrile solution containing 0.1% trifluoroacetic acid (A) and water containing 0.1% formic acid (B) in gradient elution mode. Quantification was performed using positive ion electrospray ionization (ESI), and the contents of two compounds were determined
using the multiple reaction monitoring (MRM) modes. Results: The quantitative analytical method was fully validated with respect to linearity (r > 0.9998), sensitivity, precision, accuracy (the average recovery of two impurities was 84.1% to 90.7%), and robustness. Conclusion:
Three batches of samples were detected by UPLC-MS/MS, indicating that the proposed approach was applicable for the quality evaluation of Crisaborole.
研究领域:
药物分析
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皮肤病学
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毒理学
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DOI
高影响因子
ENVIRONMENTAL SCIENCE & TECHNOLOGY
·
2024
·
IF 10.8
Shaoyang Hu,Xiangxiang Li,Guangzhao Li,Zhigang Li,Falin He,Guang Tian,Xingchen Zhao,Rutao Liu
Recently, seven dihalohydroxybenzonitriles (diHHBNs) have been determined as concerning nitrogenous aromatic disinfection byproducts (DBPs) in drinking water. Herein, eight new monohalohydroxybenzonitriles (monoHHBNs), including 3-chloro-2-hydroxybenzonitrile, 5-chloro-2-hydroxybenzonitrile, 3-chloro-4-hydroxybenzonitrile, 3-bromo-2-hydroxybenzonitrile, 5-bromo-2-hydroxybenzonitrile, 3-bromo-4-hydroxybenzonitrile, 5-iodo-2-hydroxybenzonitrile, and 3-iodo-4-hydroxybenzonitrile, were detected and identified in drinking water for the first time. Thereafter, the relative concentration–cytotoxicity contribution of each HHBN was calculated based on the acquired occurrence level and cytotoxicity data in this study, the genome-scale cytotoxicity mechanism was explored, and a quantitative structure–activity relationship (QSAR) model was developed. Results indicated that new monoHHBNs were present in drinking water at concentrations of 0.04–1.83 ng/L and exhibited higher cytotoxicity than some other monohalogenated aromatic DBPs. Notably, monoHHBNs showed concentration–cytotoxicity contribution comparable to diHHBNs, which have been previously identified as potential toxicity drivers in drinking water. Transcriptomic analysis revealed immunotoxicity and genotoxicity as dominant cytotoxicity mechanisms for HHBNs in Chinese hamster ovary (CHO-K1) cells, with potential carcinogenic effects. The QSAR model suggested oxidative stress and cellular uptake efficiency as important factors for their cytotoxicity, highlighting the importance of potential iodinated HHBNs in drinking water, such as 3,5-diiodo-2-hydroxybenzonitrile, for future studies. These findings are meaningful for better understanding the health risk and toxicological significance of HHBNs in drinking water.
研究领域:
环境化学
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毒理学
·
基因组学
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水处理
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产品关联
DOI
PubMed
高影响因子
Catalysis Science & Technology
·
2025
·
IF 4.2
Chengyang Sun,Yong Guo,Xiaohui Liu,Yanqin Wang
The upcycling of C–C bond linked polyolefins has drawn wide attention in recent years and a lot of studies have been focused on the conversion of polyolefins to hydrocarbons, while the further valorization to more value-added products has barely been developed. In this work, we developed an efficient strategy to upgrade polystyrene (PS) plastics into a single N-containing product, benzonitrile, over a NiO/CeO2 catalyst via a one-pot, two-step process. The first step is the oxidative-amination of PS to a mixture of benzamide and benzonitrile and the second step is the dehydration of benzamide to benzonitrile; finally, a single N-containing product, benzonitrile with a 50.3% yield, was achieved. Mechanism studies via control experiments in the first oxidative-amination step showed that benzaldehyde was the important intermediate, which can undergo two parallel pathways generating benzamide and benzonitrile, respectively. Following the dehydration of benzamide to benzonitrile in the second step, benzonitrile was produced as the only product. This strategy can also be extended to real-life PS plastics and a high yield of benzonitrile was achieved. This novel study provides an efficient approach for upgrading waste plastics to a single high-value product.
研究领域:
化学工程
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环境科学
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催化科学
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产品关联
DOI
高影响因子
JOURNAL OF ENVIRONMENTAL MANAGEMENT
·
2025
·
IF 8.4
Shaoyang Hu,Fangyuan Dong,Xiangxiang Li,Ning Sun,Xiaoyang Wang,Shuqi Guo,Yuntao Qi,Rutao Liu
Halohydroxybenzonitriles (HHBNs) were reported to exist in drinking water as an emerging group of nitrogen-containing aromatic disinfection byproducts (DBPs). The involvement of binding energy with catalase (CAT) as one of molecular descriptors in the quantitative structure-activity relationship model for HHBN cytotoxicity supported that oxidative stress is highly possible to be an essential cytotoxicity mechanism for HHBNs, and the disruption of cellular redox homeostasis may be partly attributed to their interactions towards CAT. However, the relevant evidence is lacking as yet. Thus, in this study, typical biomarkers for oxidative stress and damage in HHBN-treated cells were examined, and the binding interactions between HHBN and CAT were explored. Results indicated that upon exposure to 3,5-dibromo-2-hydroxybenzonitrile, the antioxidant system (e.g., CAT, superoxide dismutase, and glutathione) was disrupted, and excessive reactive oxygen species gave rise to oxidative DNA damage, which further resulted in cell apoptosis. Moreover, the binding interaction between CAT and 3,5-dibromo-2-hydroxybenzonitrile could change the structure and activity of CAT, with the formation of complexes primarily dependent on van der Waals forces and hydrogen bonding. A positive correlation was observed between HHBN cytotoxicity and inhibitory potency on the biological function of CAT, and some unidentified iodinated HHBNs warrant special attention in future owing to their potential high cytotoxicity. The above results contribute to a better understanding of the toxic mechanisms of emerging HHBN DBPs.
研究领域:
环境科学
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毒理学
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生物学
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产品关联
DOI
PubMed
高影响因子
JOURNAL OF ELECTROANALYTICAL CHEMISTRY
·
2022
·
IF 4.598
Youqun Chu,Xiaoping Zhang,Xinyu Liu,Hao Tang,Weitao Zhou,Kaiwen Li,Xin Liu,Zhaoyang Chen,Yinghong Zhu,Fengming Zhao
An efficient and mild iodide-mediated indirect electrooxidation method to prepare 2,6-dichlorobenzonitrile was developed. Cyclic voltammetry and potentiostatic electrolysis were carried out to investigate the feasibility of this approach for 2,6-dichlorobenzaldehyde. Unexpectedly, an increase in the synthetic efficiency was obtained when the solution contained chloride ions. The cyclic voltammetric results indicated that an interhalide species, namely [ICl 2 ] − , was formed during oxidation of the iodide ion in the solutions containing chloride ions; this result was in contrast to the expected formation of the less electrophilic I 2 . The strong electrophilicity of [ICl 2 ] − greatly enhanced the efficiency of the electrosynthetic approach to 2,6-dichlorobenzonitrile. Overall, this synthesis system provides a green and efficient route to 2,6-dichlorobenzonitrile, and hence, could be potentially applicable in the industrial preparation of aromatic nitriles.
研究领域:
有机化学
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电化学
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产品关联
DOI
高影响因子
DYES AND PIGMENTS
·
2019
·
IF 4.018
Xin-cen Lin,Nan Li,Wei-jing Zhang,Zhen-jie Huang,Qian Tang,Chengbin Gong,Xiang-kai Fu
In this study, the electrochromic behavior of benzonitrile compounds were investigated. For this, a series of benzonitrile compounds with different chemical structures were synthesized and their electrochemical properties were investigated by cyclic voltammetry . Electrochromic behavior of the benzonitrile derivatives were also investigated by constructing sandwich type electrochromic devices and recording the changes in the UV–vis spectra as a function of applied potential. The compounds exhibited excellent electrochromic properties such as a high optical contrast, low driving voltage , good switching stability, high coloration efficiency, and a fast response time. All five compounds had different colors (orange, yellow-green, reddish-brown, green, blue) and driving voltages that were highly dependent on their chemical structures. The results indicate that benzonitriles are good electrochromic materials and should be of interest for applications such as electrochromic smart windows , information displays, and optical storage devices.
研究领域:
材料科学
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电化学
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DOI
高影响因子
RESEARCH ON CHEMICAL INTERMEDIATES
·
2022
·Vol. 48
·期 10
·4105-4118
·
IF 3.134
Tang Wanjun,Liu Yunyi,Ding Shuang,Zhao Dongmei,Li Tingcheng,Xie Guangyong
MoV 2 O 8 micro-cuboids were environment-friendly prepared via a facile one-step solvothermal route followed by thermal treatment with vanadium pentoxide and ammonium molybdate as raw materials without using harmful solvents or surfactants. Characterization by XRD, FTIR, XPS, SEM and TEM showed that MoV 2 O 8 formed a layered structure by the stacking of nanosheets and assumed a micro-cuboid shape with a thickness of 150∓30 nm, a width of 350∓110 nm and a length of 680∓18 nm. For the first time, the catalytic properties of MoV 2 O 8 micro-cuboids were investigated for the gas-phase ammoxidation of p -chlorotoluene (PCT) to p -chlorobenzonitrile (PCBN). The as-prepared catalyst exhibited high activity and selectivity in the ammoxidation of PCT to PCBN, with a near 100% conversion and 83.6% yield.
Graphical abstract
研究领域:
材料化学
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催化化学
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纳米材料
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绿色合成
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有机反应工程
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DOI
高影响因子
LWT-FOOD SCIENCE AND TECHNOLOGY
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2024
·
IF 6
Peipei Xu,Qingling Nie,Runbing Huang,Jing Shi,Junjie Ren,Ruiyun You,Hengfang Wang,Yan Yang,Yudong Lu
Camellia oil (CAO) is a high-quality edible vegetable oil, commonly known as “Oriental olive oil," with medical value and biological activity, but easily adulterated. Currently, we developed a method that combines Surface Enhanced Raman Spectroscopy (SERS) with machine learning for the effective identification of camellia oil. SERS is essential in this context because it significantly enhances the sensitivity and specificity of the detection process, allowing for the identification of even minor adulterations that traditional methods may overlook. We employed SERS spectra of both pure and adulterated camellia oil on an NPAg sheet coated with 4-thiobenzonitrile (4MBN) at a concentration of 0.02% for the machine learning analysis. The utilization of 4MBN for signal generation within the Raman silent region further enhances the stability of spectral acquisition and ensures more accurate results. The k nearest neighbors (KNN) model exhibited superior performance, achieving a test set accuracy of 97.24%. Consequently, the NPAg sheet@ [email protected] %ER strategy, designed to amplify compositional differences in edible oils, emerges as an effective tool for rapidly verifying the authenticity of such oils.
研究领域:
食品科学
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分析化学
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生物医学工程
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产品关联
DOI
高影响因子
ChemistrySelect
·
2025
·Vol. 10
·期 13
·e202500936
·
IF 2
Xiangkang Han,Juan Xia,Lingfeng Gao,Shichen Wang,Haoqi Zhan,Zhibin Han,Zeyu Wang,Xu Sun,Qin Wei
Graphical The NiFeB hydroxide (NiFeB(OH)) with nanosheet structure is fabricated via the hydrothermal reaction. Benefitted from the incorporation of electron-deficient boron (B), the formation of high-valence nickel active centers is promoted, facilitating the electrocatalytic oxidation of benzylamine. The oxidation product is benzonitrile with no by-products generated, with the Faraday efficiency being 94.15%. Considering the slow kinetics of oxygen evolution reaction (OER) and the need for high potential, organic electro oxidation, which is more prone to occur at low potential, is adopted to replace OER process. The research method combined with hydrogen evolution reaction (HER) has gradually become the mainstream direction for the synergistic production of hydrogen and high value-added organic products. In this work, the NiFeB hydroxide (NiFeB(OH)) nanosheet was prepared. Benefited from the incorporation of electron-deficient boron (B), the NiFeB(OH) catalyst exhibited excellent catalytic activity for the electrooxidation of benzylamine (BA), with benzonitrile (BN) being successfully fabricated. The experiment further proves that the conversion from BA to BN not only has high selectivity (100%) and Faraday efficiency (94.15%), but also excellent stability, which can achieve long-term operation. The excellent catalyst studied in this work provides new ideas and methods for the efficient production of benzonitrile, an organic intermediate.
研究领域:
电催化
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材料科学
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有机合成
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产品关联
DOI
高影响因子
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
·
2023
·
IF 4.4
Li Gao,Yang Liu,Mengyao Zhang,Xinyi Zhao,Yuai Duan,Tianyu Han
We report in this study a photochromic benzonitrile Schiff base, ( E )-4-((2-hydroxy-4-methoxybenzylidene)amino)benzonitrile ( HMBAB ). The molecular design, synthesis, aggregation-induced emission (AIE) as well as the quantum chemical calculations were outlined. In particular, HMBAB would undergo a reversible tautomerism in response to UV exposure, exhibiting remarkable changes in both absorption and emission: the compound shows yellow color and green-yellow luminescence; after UV exposure, the changes into orange-red while the luminescence is dramatically quenched, accompanied by a large bathochromic-shift. In addition, the photochromic state can be fully recovered via thermal treatment. Such reversible dual-channel photochromism was investigated using UV–vis reflectance spectroscopy and colorimeter, wherein a gradient change with time and a high fatigue resistance in cycle use was recorded. The photochromism is quantified by well-established RGB and Lab color space, in which the color change can be accurately analyzed by the chromatic aberration (Δ E* Lab ). Sensitivity test gives a two-stage linear relation between Δ E* Lab and UV intensity, by which a limit of detection (LOD) as low as 67 μW/cm 2 is obtained. HMBAB was further fabricated into a paper-based wearable sensor, capable of being integrated into a chest card or a bracelet. It exhibits various degrees of color change in different sunlight environments, which can be readily observed by naked eyes, providing an early warning for high-dose UV radiations.
研究领域:
材料科学
·
化学
·
生物医学工程
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DOI
PubMed
高影响因子
WATER RESEARCH
·
2022
·
IF 13.4
Shaoyang Hu,Han Yeong Kaw,Lizhong Zhu,Wei Wang
Halogenated aromatic disinfection byproducts (DBPs) exhibited similar total organic halogen levels in chlorinated drinking water samples as compared with aliphatic ones, and they predominantly accounted for the overall toxicity of the samples. Among the reported halogenated aromatic DBPs, halonitrophenols (HNPs) have received particular attention in recent years due to the relatively high risk in drinking water. In this study, a new group of halogenated aromatic DBPs were detected and then proposed to be halohydroxybenzonitriles (HHBNs) by employing the ultra-performance liquid chromatography/tandem mass spectrometers. Thereafter, the specific HHBN species in drinking water were theoretically speculated and then thoroughly identified with standard compounds. Their occurrence in drinking water was investigated, their cytotoxicity was evaluated, and their stability in the presence of chlorine was assessed. Seven newly identified HHBNs, including 3,5-dichloro-4-hydroxybenzonitrile, 3,5-dichloro-2-hydroxybenzonitrile, 5-bromo-3-chloro-4-hydroxybenzonitrile, 5-bromo-3-chloro-2-hydroxybenzonitrile, 3,5-dibromo-4-hydroxybenzonitrile, 3,5-dibromo-2-hydroxybenzonitrile, and 3,5-diiodo-4-hydroxybenzonitrile, showed 100% detection frequency in the collected drinking water samples with concentrations up to 36 ng/L. HHBNs exhibited significantly higher cytotoxicity in Chinese hamster ovary cells than regulated DBPs (e.g., trihalomethanes and haloacetic acids), which might be contributed by their cellular uptake efficiency and nucleophilicity. The seven HHBNs were proved to undergo transformation during chlorination following pseudo-first-order decay with half-lives in the range of 9–63 h. More importantly, in comparison to HNPs, which showed relatively high toxicity and strong stability among the halogenated aromatic DBPs, HHBNs presented comparable concentration-cytotoxicity contribution (50%) and slightly weaker stability (43%), suggesting that HHBNs should be a new group of DBPs of concern in drinking water.
研究领域:
环境科学
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毒理学
·
公共卫生
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DOI
PubMed
高影响因子
JOURNAL OF CATALYSIS
·
2025
·
IF 6.5
Weidong Liu,Jianguo Liu
Benzylamine production from the hydrogenation of nitrile is attractive, but most of the catalysts are complicated and costly. In this paper, a simple synthesis of self-nitrogen-doped carbon-supported nickel biobased sustainable catalyst (Ni-JKS-600) for benzylamine hydrogenation with benzonitrile has been reported. The catalyst has high specific surface area, abundant micro-mesoporous structure and nickel hydrogenation active site. By optimizing the reaction conditions, a mild reaction condition (120 ℃, 2 MPa H 2 , 3 h) was determined, and it was found that the solvent had a significant effect on the selectivity of benzylamine, and the selectivity of benzylamine could reach 97.08 % when ammonia methanol was used as the solvent. Ni-JKS-600 catalyst is superior to precious metal catalysts (Ru, Pt, Ir, Pd) in aniline selectivity, and is comparable to Raney nickel catalyst, which shows its potential application in industrial production of amines. The catalyst uses cheap and widely available chitin as carbon and nitrogen source, and has the characteristics of green economy with simple preparation method and low cost. It is expected to replace precious metal catalyst for efficient production of benzylamine in the future.
研究领域:
催化化学
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绿色化学
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产品关联
DOI
高影响因子
危险品化学品经营许可证（带存储）