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CuAAC反应
RESEARCH ON CHEMICAL INTERMEDIATES · 2025 · IF 3.5

Copper immobilized on glycine-functionalized poly(vinyl chlolide): low cost, highly active, recyclable catalyst at part-per million level for CuAAC reaction in water

Zeng Fang,Zhang Shuyao,Lin Ting,Li Yiqun,Xiao Meng

A novel Cu catalyst immobilized on glycine-functionalized poly(vinyl chloride) (Cu@Gly-PVC) was synthesized conveniently. The as-prepared catalyst was fully characterized by FTIR, SEM, EDS, elemental mapping, XPS, TGA, ICP, and EA analysis. The Cu(II) ions were uniformly distributed on the as-prepared Gly-PVC matrix via coordinated by carboxylic groups in a bidentate bridging pattern. This catalyst can be used at ppm levels in water for alkyne–azide cycloadditions (CuAAC) reactions, producing high yields of 1,2,3-triazoles. The present methodology offers several merits such as low catalyst loading, high catalytic activity, excellent yields, short reaction times, environmentally friendly reactions, simple operations, and compatibility of wide range of substrates. Furthermore, the catalyst can be easily isolated from the reaction mixture through simple filtration and retains remarkable reusability and catalytic activity even after four consecutive reaction cycles. Graphical abstract

CAS / MDL: 100-44-7
研究领域: 有机化学 · 材料科学 · 绿色化学
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ANALYTICA CHIMICA ACTA · 2021 · IF 6.558

Single nanoparticle identification coupled with auto-identify algorithm for rapid and accurate detection of L-histidine

Shuting Chen,Weijia Wang,Shaohua Xu,Caili Fu,Shuyi Ji,Fang Luo,Cuiying Lin,Bin Qiu,Zhenyu Lin

In this work, an auto-identify sensor was constructed for rapid and high-precision detection of L-histidine. The proposed strategy is based on the auto-identify algorithm and the aggregation of alkynyl and azide functionalized gold nanoparticles induced by the Cu + catalyzed azides and alkynes cycloaddition (CuAAC) reaction. Specially, the color of scattering light spots for the aggregated gold nanoparticle (AuNPs) caused by CuAAC reaction was quite different from that of the monomers . However, L-histidine can bind to Cu 2+ and inhibits the production of Cu + , hence preventing the aggregation of AuNPs. Therefore, there is a distinct change of color as the addition of L-histidine under dark-field microscopy. Then, L-histidine can be quantitatively detected by combining the color change with the Meanshift algorithm accurately and automatically. Such proposed method has been successfully applied for the detection of L-histidine in serum sample with satisfying result.

研究领域: 分析化学 · 纳米技术 · 生物化学
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BIOORGANIC CHEMISTRY · 2024 · IF 4.5

A CuSO4/Bicinchoninic acid/Reducing sugar based stable and non-ROS catalyst system for the CuAAC reaction in bioanalysis

Yuchen Wang,Shi-Chao Lu,Hui Wen,Chunyue Zhao,Yanfei Jiang,Huaqing Cui

The limitations of commonly used sodium ascorbate-based catalyst system for copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction include excess production of reactive oxygen species and rapid catalyst deactivation. In this study instead of using a highly active reducing agent, such as, sodium ascorbate, we chose reducing sugar as a mild reducing agent to build up the catalyst system for CuAAC reaction. Interestingly, the bicinchoninic acid (BCA) assay system containing reducing sugar satisfies the essential elements of the catalyst system for CuAAC reaction. We found that CuSO 4 /BCA/Reducing sugar system can catalyze the CuAAC reaction but with low yield. Rational analyses of various parameters in CuSO 4 /BCA/Glucose catalyst system suggested storage at room temperature might enhance the catalytic activity, which was proven to be the case. Importantly, the system remains stable at room temperature and minimal H 2 O 2 was detected. Notably, our study showed that the coordination between the slow reduction of Cu(I) by reducing sugar and the selective chelation of Cu(I) by BCA is key to developing this system. The CuSO 4 /BCA/Reducing sugar catalyst system was successfully applied to various CuAAC reaction based bioanalyses, and it is suitable for the CuAAC reaction based bioanalyses that are sensitive to ROS or request long reaction time.

研究领域: 化学 · 生物化学 · 分析化学 · 催化
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JOURNAL OF INORGANIC BIOCHEMISTRY · 2022 · IF 4.336

Unlocking the potential of iridium and ruthenium arene complexes as anti-tumor and anti-metastasis chemotherapeutic agents

Mengdi Lv,Xiaoting Qian,Shijie Li,Jie Gong,Qun Wang,Yong Qian,Zhi Su,Xuling Xue,Hong-Ke Liu

It is a major challenge to design novel multifunctional metal-based chemotherapeutic agents for anti-tumor and anti-metastasis applications. Two complexes ( OA-Ir and OA-Ru ) were synthesized via CuAAC (copper-catalyzed azide-alkyne cycloaddition) reaction from nontoxic Ir - N 3 or Ru - N 3 species and low toxic alkynyl precursor OA-Alkyne, and exhibited satisfactory anti-tumor and anti-metastasis pharmacological effects . Conjugation of Oleanolic acid (OA) and metal-arene species significantly enhanced the cytotoxicity in A2780 cells compared to the precursors through mitochondrial-induced autophagy pathway. Moreover, the two complexes could inhibit the cell metastasis and invasion through damage of actin dynamics and down-regulation of MMP2/MMP9 proteins. Combination of two precursors improved the lipophilicity and biocompatibility, simultaneously enhanced the cell uptake and the mitochondrial accumulation of metal-arene complexes, which caused mitochondrial membrane potential damage, oxidative phosphorylation , ATP depletion and autophagy. Besides, OA-Ir and OA-Ru displayed excellent activity to disintegrate the 3D multicellular tumor spheroids , showing potential for the treatment of solid tumors. This work provides a new way for developing novel metal-based complexes via CuAAC reaction for simultaneously inhibiting tumor proliferation and metastasis.

研究领域: 化学 · 药理学 · 癌症研究 · 材料科学
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