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首页> 外文期刊>The Journal of Organic Chemistry >Anion Transporters Based on Noncovalent Balance including Anion-pi, Hydrogen, and Halogen Bonding
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Anion Transporters Based on Noncovalent Balance including Anion-pi, Hydrogen, and Halogen Bonding

机译：基于非共价平衡的阴离子运输器，包括阴离子 - PI，氢气和卤素键合

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摘要

Anion transmembrane transport mediated by novel noncovalent interactions is of central interest in supramolecular chemistry. In this work, a series of oxacalix[2]arene[2]triazine-derived transporters 1 and 2 bearing anion-pi-, hydrogen-, and halogen-bonding sites in rational proximity were designed and synthesized by a one-pot strategy starting from gallic acid ester derivatives and mono- or di-halogen-substituted triazines. 1H NMR titrations demonstrated efficient binding of 1 and 2 toward Cl and Br in solution, giving association constants in the range of 10(2)-10(4) M-1. Cooperation of anion-pi, hydrogen, and halogen bonding was revealed as a driving force for anion binding by single-crystal structures of two complexes and density functional theory calculations. Fluorescence assays indicated that compounds 1 are efficient chloride transporters with effective concentrations (EC50) falling in the range of 3.17.4 mu M and following an order of 1a > 1b > 1c > 1d. The contribution of halogen bonding and cooperative noncovalent bonds to ion transport was then discussed. Significantly, transporters 1 exhibit high anticancer activity. In the presence of 1 and KCl (60 mM), the cell survival of HCT116 reduces to 11.924.9% with IC50 values in the range of 52.366.4 mu M
机译：由新型非共价相互作用介导的阴离子跨膜运输是对超分子化学的核心感兴趣。在这项工作中，通过一个单锅策略开始设计和合成理性接近的一系列氧化鼠[2]芳烯[2]芳烯[2]三嗪衍生的转运蛋白，致力于理性接近的氢气和卤素键合位点来自Gallic酸酯衍生物和单卤素取代的三嗪。 1H NMR滴定证明了在溶液中的1和2的有效结合，在溶液中，给出了10（2）-10（4）m-1的关联常数。阴离子-PI，氢气和卤素键合的合作被揭示为由两个复合物的单晶结构的阴离子结合的驱动力和密度官能理论计算。荧光测定表明，化合物1是有效浓度（EC50）的有效氯化物转运蛋白，其范围为3.17.4μm，并按照1a> 1b> 1c> 1d的顺序。然后讨论了卤素键合和合作非共价键对离子转运的贡献。显着地，转运蛋白1表现出高抗癌活动。在1和KCl（60mM）的存在下，HCT116的细胞存活率在10.924.9％的IC 50值中减少到52.366.4 mu m的范围内

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  • 来源
    《The Journal of Organic Chemistry》 |2019年第14期|共11页
  • 作者

    Huang Wen-Long; Wang Xu-Dong; Li Sen; Zhang Rui; Ao Yu-Fei; Tang Jun; Wang Qi-Qiang; Wang De-Xian;

  • 作者单位

    Chinese Acad Sci Inst Chem CAS Key Lab Mol Recognit &

    Funct Beijing Natl Lab Mol Sci Beijing 100190 Peoples R China;

    Chinese Acad Sci Inst Chem CAS Key Lab Mol Recognit &

    Funct Beijing Natl Lab Mol Sci Beijing 100190 Peoples R China;

    Chinese Acad Sci Inst Chem CAS Key Lab Mol Recognit &

    Funct Beijing Natl Lab Mol Sci Beijing 100190 Peoples R China;

    China Agr Univ State Key Lab Agrobiotechnol Beijing 100193 Peoples R China;

    Chinese Acad Sci Inst Chem CAS Key Lab Mol Recognit &

    Funct Beijing Natl Lab Mol Sci Beijing 100190 Peoples R China;

    China Agr Univ State Key Lab Agrobiotechnol Beijing 100193 Peoples R China;

    Chinese Acad Sci Inst Chem CAS Key Lab Mol Recognit &

    Funct Beijing Natl Lab Mol Sci Beijing 100190 Peoples R China;

    Chinese Acad Sci Inst Chem CAS Key Lab Mol Recognit &

    Funct Beijing Natl Lab Mol Sci Beijing 100190 Peoples R China;

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  • 正文语种 eng
  • 中图分类 有机化学;
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