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Poly-histidine grafting leading to fishbone-like architectures

机译：多组氨酸嫁接导致鱼骨样架构

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摘要

A small series of Morita-Baylis-Hillman adduct (MBHA) derivatives was synthesized and made to react with imidazole, N-acetylhistidine, and N-acetylhexahistidine as models of poly-histidine derivatives. Intriguingly, the reaction of MBHA derivatives 1a and b with imidazole in acetonitrile-phosphate buffered saline (PBS) gave the imidazolium salt biadducts 3a and b as the main reaction products. These results were confirmed by experiments performed with N-acetylhistidine and 1b and suggested the possible occurrence of these structures in the products of poly-histidine labeling with MBHA derivatives 1a and b. These compounds were then transformed into the corresponding water-soluble derivatives 1c-e by introducing oligo(ethylene glycol) chains and their reactivity was evaluated in preliminary experiments with imidazole and then with N-acetylhexahistidine in PBS. The structure of polymeric materials Ac-His-6-MBHA-1d and Ac-His-6-MBHA-1e obtained using ten-fold excesses of compounds 1d and e was investigated using mass spectrometry, NMR spectroscopy, and photophysical studies, which suggested the presence of biadduct residues in both polymeric materials. These results provide the basis for the preparation of fishbone-like polymer brushes, the characterization of their properties, and the exploration of their potential applications in different fields of science such as in vivo fluorogenic labeling, fluorescence microscopy, protein PEGylation, up to the production of smart materials and biosensors.
机译：合成了一小编Morita-Baylis-Hillman加合物（MBHA）衍生物，并使其与咪唑，N-乙酰氨基氨氨酸和N-乙酰烷基氨基和N-乙酰基烷基氨基反应为多组织衍生物的模型。有趣的是，MBHA衍生物1a和b与咪唑在乙腈 - 磷酸盐缓冲盐水（PBS）中的反应使咪唑鎓盐Biadducts 3a和B作为主要反应产物。这些结果通过用N-乙酰基氨基和1B进行的实验证实，并表明在MBHA衍生物1a和b的多组氨酸标记产物中可能出现这些结构。然后通过引入寡核苷酸（乙二醇）链将这些化合物转化到相应的水溶性衍生物1C-E中，并在用咪唑中的初步实验中评价它们的反应性，然后用PBS中的N-乙酰萘氨基氨基。使用质谱法，NMR光谱和光药研究研究了使用10倍过量的化合物1D和E获得的聚合物材料AC-HIS-6-MBHA-1D和AC-HIS-6-MBHA-1E的结构两种聚合物材料中的Biadduct残基的存在。这些结果为制备鱼肉状聚合物刷子，其性质表征的基础，以及在不同科学领域的潜在应用的探索，如体内荧光标记，荧光显微镜，蛋白质聚乙二醇，达到生产智能材料和生物传感器。

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  • 来源
    《RSC Advances》 |2018年第16期|共19页
  • 作者

    Razzano Vincenzo; Paolino Marco; Reale Annalisa; Giuliani Germano; Donati Alessandro; Giorgi Gianluca; Artusi Roberto; Caselli Gianfranco; Visintin Michela; Makovec Francesco; Battiato Salvatore; Samperi Filippo; Villafiorita-Monteleone Francesca; Botta Chiara; Cappelli Andrea;

  • 作者单位

    Univ Siena Dipartimento Biotecnol Chim &

    Farm European Res Ctr Drug Discovery &

    Dev Via A Moro 2 I-53100 Siena Italy;

    Univ Siena Dipartimento Biotecnol Chim &

    Farm European Res Ctr Drug Discovery &

    Dev Via A Moro 2 I-53100 Siena Italy;

    Univ Siena Dipartimento Biotecnol Chim &

    Farm European Res Ctr Drug Discovery &

    Dev Via A Moro 2 I-53100 Siena Italy;

    Univ Siena Dipartimento Biotecnol Chim &

    Farm European Res Ctr Drug Discovery &

    Dev Via A Moro 2 I-53100 Siena Italy;

    Univ Siena Dipartimento Biotecnol Chim &

    Farm European Res Ctr Drug Discovery &

    Dev Via A Moro 2 I-53100 Siena Italy;

    Univ Siena Dipartimento Biotecnol Chim &

    Farm European Res Ctr Drug Discovery &

    Dev Via A Moro 2 I-53100 Siena Italy;

    Rottapharm Biotech SpA Via Valosa Sopra 9 I-20900 Monza Italy;

    Rottapharm Biotech SpA Via Valosa Sopra 9 I-20900 Monza Italy;

    Rottapharm Biotech SpA Via Valosa Sopra 9 I-20900 Monza Italy;

    Rottapharm Biotech SpA Via Valosa Sopra 9 I-20900 Monza Italy;

    CNR IPCB UOS Catania Via Gaifami 18 I-95126 Catania Italy;

    CNR IPCB UOS Catania Via Gaifami 18 I-95126 Catania Italy;

    CNR Ist Studio Macromol Via A Corti 12 I-20133 Milan Italy;

    CNR Ist Studio Macromol Via A Corti 12 I-20133 Milan Italy;

    Univ Siena Dipartimento Biotecnol Chim &

    Farm European Res Ctr Drug Discovery &

    Dev Via A Moro 2 I-53100 Siena Italy;

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