CHINESE JOURNAL OF CATALYSIS
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2019
·
IF 4.914
Zhi-Hua Zhou,Xiao Zhang,Yong-Fu Huang,Kai-Hong Chen,Liang-Nian He
Inexpensive and efficient Cu(I) catalysis is reported for the synthesis of α-hydroxy ketones from propargylic alcohols, CO 2 , and water via tandem carboxylative cyclization and nucleophilic addition reaction. Notably, hydration of propargylic alcohols can be carried out smoothly under atmospheric CO 2 pressure, generating a series of α-hydroxy ketones efficiently and selectively. This strategy shows great potential for the preparation of valuable α-hydroxy ketones by using CO 2 as a crucial cocatalyst under mild conditions.
研究领域:
有机化学
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催化化学
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DOI
高影响因子
ACS Sustainable Chemistry & Engineering
·
2016
·
IF 5.267
Yuling Zhao,Jikuan Qiu,Li Tian,Zhiyong Li,Maohong Fan,Jianji Wang
Carbon dioxide (CO2) is an abundant and renewable feedstock for the production of high-value chemicals. Herein, CuI and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) were employed as an efficient catalyst system to synthesize 2-oxazolidinones through the coupling reaction of CO2 and propargylic amines. It was found that this cost-competitive catalyst system could efficiently catalyze the reaction within only 4 h at atmospheric pressure CO2, and a wide range of substrates were suitable for this reaction. Various target products were obtained in excellent yields. Furthermore, the catalytic mechanism of the CuI/DBU system was investigated by using density functional theory. It was shown that copper(I) and DBU played synergistic roles in activating both the C≡C triple bond and the amino group of propargylic amines in the reaction.
研究领域:
有机化学
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催化化学
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产品关联
DOI
高影响因子
RSC Advances
·
2016
·Vol. 6
·期 35
·29638-29645
·
IF 3.289
Xin Ge,Xinzhi Chen,Chao Qian,Shaodong Zhou
Ullmann type C–N coupling reaction catalyzed by copper(I) with D-glucosamine derivatives as promoters was studied by means of combined experimental/theoretical investigation. The catalytic role of D-glucosamine was addressed. In contrast with previous speculations, the amino group may not count in the catalytic cycle in which the oxidative addition/reductive elimination mechanism works. Experimental results are in good agreement with theoretical findings. Extensive work indicates the wide applicability of the C–N coupling strategy exploited in this work.
研究领域:
有机化学
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催化化学
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药物化学
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计算化学
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合成方法学
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生物正交化学
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金属有机化学
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DOI
高影响因子
ORGANIC PROCESS RESEARCH & DEVELOPMENT
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2019
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IF 3.327
Xiaoyi Li,Bo Jin,Zhicheng Guo,Shijin Chu,Rufang Peng
The copper(I)-catalyzed 1,3-dipolar cycloaddition of azides and alkynes provides diverse building blocks for chemical synthesis, biochemistry, pharmaceutical industries, and materials science. To provide a good theoretical support for industrial amplification reaction, it is significant to study the catalytic properties and the corresponding kinetics of a given reaction. In this article, the reaction kinetics and thermodynamics of “click reaction” between benzyl azide and different alkynes were investigated by microcalorimetry. Benzyl azide and ethyl propiolate were used as model reactions. The effects of a variety of parameters were studied in a calorimeter to establish the kinetics and mechanism of the reaction under isothermal conditions. The activation energies for the reaction of benzyl azide with 4-nitrophenylacetylene, ethyl propiolate, and 3-butyn-2-one were 22.99 ± 0.13, 55.81 ± 0.74, and 56.75 ± 0.65 kJ mol–1, respectively. The difference of reaction kinetics of different alkynes was explained by the reaction mechanism combined with theoretical calculations, and the reaction is intrinsically kinetically controlled.
研究领域:
化学合成
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生物化学
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制药工业
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材料科学
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物理化学
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DOI
高影响因子
RSC Advances
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2015
·Vol. 5
·期 92
·75722-75727
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IF 3.84
Dou Wang,Chenchen Ge,Lin Wang,Xuerong Xing,Lingwen Zeng
Copper(II) ions (Cu2+) at a high concentration are harmful to human health. Herein a simple and enzyme-free lateral flow biosensor for the rapid detection of Cu2+ based on copper(I) ion (Cu+)-catalyzed click chemistry has been constructed for the first time. In the presence of sodium ascorbate, Cu2+ was reduced to Cu+, which could catalyze the cycloaddition between azide-DNA and alkyne/biotin-DNA in aqueous solution. The ligated DNA product could then be immobilized onto the test zone of the lateral flow biosensor to form a red band which could be unambiguously read by the naked eye. Taking advantage of the optical properties of gold nanoparticles (AuNPs) and high efficiency and selectivity of Cu+-catalyzed click chemistry, this assay enabled the visual detection of Cu2+ as low as 100 nM with excellent specificity. In comparison with conventional methods, this biosensor is more simple to operate and more cost-effective to use, and therefore has great potential in point-of-care diagnosis and environmental monitoring.
研究领域:
分析化学
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环境科学
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生物传感器
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材料科学
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产品关联
DOI
高影响因子
Journal of Materials Chemistry B
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2017
·Vol. 5
·期 11
·2078-2085
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IF 4.543
Xiangxiang Liu,Bowei Liu,Sijia Gao,Zhaocheng Wang,Ye Tian,Man Wu,Shidong Jiang,Zhongwei Niu
Plant viruses have been applied broadly in nanomedical applications profiting from their monodisperse structure, biocompatibility, easy modification, and non-pathogenicity in animals. Here we report a tobacco mosaic virus (TMV) based drug delivery system bearing carbohydrates as targeting ligands. Mannose (Man) and lactose (Lac) moieties were separately conjugated to the exterior surface of TMV (TMV-Man and TMV-Lac) through an efficient copper(I)-catalyzed azide–alkyne cycloaddition. Cisplatin (CDDP), an anticancer drug, was directly loaded into the TMV cavity (CDDP@TMV, CDDP@TMV-Man and CDDP@TMV-Lac) via a metal coordination bond. Through the specific recognition between carbohydrates and glycoproteins in cell membranes, these TMV based vectors show specificity in different cell lines: in the galectin-rich MCF-7 cell line, CDDP@TMV-Man shows enhanced endocytosis and apoptosis efficiency; in the asialoglycoprotein receptor (ASGPR)-overexpressing HepG2 cell line, CDDP@TMV-Lac shows superiority in endocytosis and apoptosis. This research provides a new strategy for tumor-targeted cisplatin delivery.
研究领域:
纳米医学
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药学
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病毒学
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癌症研究
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产品关联
DOI
PubMed
高影响因子
BIOTECHNOLOGY PROGRESS
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2012
·Vol. 28
·期 3
·856-861
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IF 2.34
Xiao-Yuan Li,Tai-Hang Li,Jin-Shan Guo,Ying Wei,Xia-Bin Jing,Xue-Si Chen,Yu-Bin Huang
Monomethyl poly(ethylene glycol) (mPEG)-modified bovine serum albumin (BSA) conjugates (BSA-mPEG) were obtained by the mild Cu(I)-mediated cycloaddition reaction of azided BSA (BSA-N 3 ) and alkyne-terminated mPEG. The structure and characteristics of BSA-mPEG conjugates were thoroughly investigated. There were about two PEG chains conjugated onto each BSA molecule as determined by matrix-assisted laser desorption/ionization time of flight (MALDI-TOF) analysis. The intrinsic nonspecific binding ability of BSA was used for adsorption and sustained release of both rifampicn and 5-fluorouracil (5-FU). The helical structures of BSA were preserved to a large extent after modification and drug adsorption on BSA was confirmed via circular dichroism spectroscopy. Drugs adsorbed onto the conjugated formulation to a lesser extent than on BSA due to mPEG modification. The in vitro release of both rifampicin and 5-FU, however, indicated that BSA-mPEG can function as a drug carrier. Overall, the click reaction provided a convenient tool for the pegylation of BSA. The biological activity of the BSA-mPEG conjugates, including the drug transportation capacity and biocompatibility, were largely retained. © 2012 American Institute of Chemical Engineers Biotechnol. Prog.,, 2012
研究领域:
药学
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化学
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生物技术
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药物递送系统
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产品关联
DOI
PubMed
高影响因子
MICROCHEMICAL JOURNAL
·
2024
·
IF 4.9
Xiao-Kang Fu,Si-Qi Han,Xiao-Bo Zhao,Jing-Yan Kang,Wei Ha,Yan-Ping Shi
Steroid hormone residues in food are a significant sources of endocrine disrupting chemicals (EDCs) that can adversely affect public health. However, the current analytical methods for determining steroid hormones using liquid chromatography-tandem mass spectrometry (LC-MS/MS) can be challenging due to the poor ionization efficiency of steroid hormones and the matrix effect of complex food samples. Herein, based on Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction and stable isotope labeling (SIL) technique, a novel pair of chemoselective probes ABI / d 5 -ABI was precisely designed and synthesized. This pair of probes comprises a H/D isotope tag, a linker, a reactive site azido group (N 3 ) and a MS tag (imidazolium salt). The probe ABI was employed to label ethynyl-containing steroid hormones in real samples and d 5 -ABI was applied to label standards, respectively, followed by mixing the two labeled samples for high performance (HP)LC-MS/MS analysis. It was found that the ionization efficiencies of target analytes were increased by 17–4532 folds after ABI labeling. More importantly, the heavy labeled samples serving as internal standards (ISs) can effectively compensate matrix effect during HPLC-MS/MS analysis. Finally, the proposed SIL-HPLC-MS/MS method was successfully used to highly sensitive determine four synthetic steroid hormones in food samples (milk, pork and egg). Furthermore, the good detection limits (0.015–0.020 ng/mL), satisfactory recoveries (75.7–122.9 %), and precisions (RSDs less than 9.2 %) were obtained. Hence, the established method not only provides new insights in designing SIL probes for determination of ethynyl-containing analytes within complex matrix, but also extends the application of CuAAC reaction in the field of food chemistry.
研究领域:
分析化学
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食品科学
·
质谱技术
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产品关联
DOI
高影响因子
TALANTA
·
2017
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IF 4.162
Yanzhe Li,Zhe Sheng,Chuanlei Zhu,Wei Yin,Changhu Chu
Crown ether is a type of typical macrocyclic polyether compounds, which can produce strong interactions with cationic species, such as metal ions and protonated amines due to its cavity structure and the strong electronegative effect of heteroatoms on the crown ether ring. In this paper, a type of silica based crown ether stationary phase was prepared by covalently bonding dibenzo-18-crown 6-ether (DBCE) on silica gel via copper (I) catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC). The tetraazido DBCE was rapidly prepared by bromomethylation and subsequent azido substitution of DBCE. Finally, this key intermediate was covalently bonded to silica beads by click chemistry to get click-DBCE. Its structure was confirmed by FT-IR and elemental analysis, and the structures of all related intermediates were confirmed by NMR, IR and MS spectra. The crown ether based stationary phase showed good chromatography characteristics and column efficiency (up to 43,553 plates m -1 theoretical plate number is obtained in the case of fluoranthene) under reverse phase liquid chromatographic (RPLC) model. The primary chromatographic evaluation showed that click-DBCE displayed better chromatography efficiency than commercial C18 stationary phase (THERMO BDS HYPERSIL), when they were applied in the separation of regio-isomers of benzene, polycyclic aromatic hydrocarbons (PAHs) and macrolide pharmaceuticals. Furthermore, this stationary phase could also be used to separate fullerenes under normal phase mode, and in this case, 1-chloronaphthalene was suitable additive for improving chromatographic separation ability.
研究领域:
分析化学
·
材料科学
·
色谱学
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产品关联
DOI
PubMed
高影响因子
CHEMICAL ENGINEERING JOURNAL
·
2022
·
IF 16.744
Sa Wang,Shuqing Yang,Zhuolin Cui,Xueyan Liu,Yu Yang,Tao Wang,Wenjuan Ma,Yubin Zhou,Ruizheng Liang,Dan Yan,Huizhi Chen
Precise activation of therapeutic molecules in tumor tissues is the key step to ensure targeted antitumor performance and reduce adverse effects towards normal tissues and organs. Although the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC), i.e., bioorthogonal chemistry, has been used for the rapid synthesis of anticancer drugs in cells, it remains a great challenge to realize precise in vivo drug synthesis in tumor sites for precise cancer treatment. In this work, we first report the in-situ activation of CuAl-layered double hydroxide (CuAl-LDH) nanosheets to realize Cu(I)-catalyzed bioorthogonal chemistry in vivo in tumor microenvironment (TME) for precise chemotherapy and chemodynamic therapy (CDT). The Cu(II) ions in the biocompatible CuAl-LDH nanosheets can be in-situ reduced to Cu(I) ions partially by the overexpressed glutathione in TME. The generated Cu(I) can serve as a catalyst to catalyze the CuAAC reaction between alkyne and azide in TME, thus realizing in vivo drug synthesis for precise chemotherapy. Meanwhile, the generated Cu(I) can catalyze the Fenton-like reaction to generate toxic hydroxyl radicals (⋅OH) from H 2 O 2 in TME for CDT. Therefore, CuAl-LDHs can be used for the targeted synergistic chemotherapy and CDT to achieve highly precise and efficient elimination of cancer cells in vitro and inhibition of tumors in vivo .
研究领域:
纳米技术
·
癌症治疗
·
生物化学
·
材料科学
✓ 已验证
产品关联
DOI
高影响因子
ANALYTICAL CHEMISTRY
·
2021
·
IF 6.986
Xianlong Zhang,Yongning Wu,Juhong Chen,Yan Yang,Guoliang Li
The copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) click reaction has drawn increasing attention in the field of analytical science. However, the poor stability of Cu(I) usually hinders not only the simplicity of the click reaction but also its applications in precise analyses. Therefore, the development of a nanocatalyst containing stable Cu(I) is of great significance for broadening the application of CuAAC-based assays. Herein, inspired by the active center structure of natural multicopper oxidases (MCOs), we successfully prepared a novel nanocatalyst containing abundant stable Cu(I) as an artificial “clickase” (namely, CCN) by using glutathione to stabilize Cu(I). The stability and enzyme-like catalytic activity in the CuAAC reaction of the prepared CCN clickase were studied, and the catalytic mechanism of the CCN clickase-mediated CuAAC reaction between 3-azide-7-hydroxycoumarin (Azide 1) and propargyl alcohol (Alkyne 2) was also revealed. Compared with the existing solid CuO nanocatalysts used in CuAAC-based assays, CCN clickases exhibited plenty of superior properties (including high stability, excellent catalytic activity, no requirements of dissolution and reducing agents/radical initiator during the detection, well-defined porosities benefiting the substrate diffusion, and good biocompatibility), which can greatly increase the reaction efficiency and shorten the detection time. Encouraged by these remarkable performances, CCN clickases were used as labels to establish a new catalytic click fluorescence immunoassay for foodborne pathogens. Notably, the proposed CCN clickase-based immunoassay exhibited high analytical performances for the quantification of Salmonella enteritidis in the linear range of 102–106 CFU/mL with a limit of detection as low as 11 CFU/mL. The developed method has also been used in the determination of S. enteritidis in food samples, showing its great potential in the detection of foodborne pathogens.
研究领域:
分析化学
·
纳米技术
·
免疫学
·
食品安全
✓ 已验证
DOI
PubMed
高影响因子
Polymer Chemistry
·
2019
·Vol. 11
·期 6
·1198-1210
·
IF 4.76
Junnan He,Nan Zheng,Dan Xie,Yubin Zheng,Wangze Song
Multicomponent polymerization (MCP), as a powerful synthetic tool, has been widely utilized to prepare diverse functional polymers for optical, electronic, and biomedical applications. Here, a Cu(I)-catalyzed MCP toward biodegradable polymers with diverse responsiveness in tumor microenvironments (TMEs) is developed using diynes, sulfonyl azides and a series of TME-responsive, cleavable diols. The resulting polymers showed high molecular weights (up to 12000 g mol−1) and high yields (up to 96%). The biodegradable polymers displayed excellent degradation performance in various simulated TMEs (reactive oxygen species, high reducing reagent, and low pH). One typical photosensitizer, tetraphenyl porphyrin (TPP), was conjugated to the side chains of the polymers for potential application in photodynamic therapy (PDT). The TPP-polymer conjugates displayed enhanced fluorescence intensity and higher singlet oxygen quantum yield than the TPP monomer due to the controlled conjugation efficiency and the unique MCP structure, which provided a complementary strategy to limit the undesired aggregation-caused-quenching (ACQ) effect of PDT.
研究领域:
聚合物化学
·
生物医学工程
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材料科学
·
癌症治疗
✓ 已验证
产品关联
DOI
高影响因子
危险品化学品经营许可证（带存储）