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Synthesis, characterization and biological evaluation of cationic porphyrin-terpyridine derivatives

机译：阳离子卟啉 - 萜烯衍生物的合成，表征及生物学评价

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摘要

A simple access to a new series of cationic porphyrin-terpyridine derivatives is described. The key step to obtain the required neutral precursors as major products involved a Krohnke type approach. The methodology allowed also the isolation of the respective benzoporphyrins and porphyrin-chalcone type derivatives, and in one case a new 2-(2,4-terpyridin-6-yl)-porphyrin. The quaternization of the pyridyl groups was performed in the presence of the adequate alkyl iodide affording the dicationic derivatives in excellent yields. All the new conjugates were fully characterised and it was found that the cationic isomers can be efficiently differentiated by ESI-MS, as their behaviour can be intensively studied by mass spectrometry. The new methylated cationic porphyrin-terpyridine derivatives demonstrate an ability to generate singlet oxygen and their efficacy to photoinactivate bioluminescent Gram-negative E. coli was evaluated. A reduction in the bioluminescence signal, up to 5.4 log, was obtained with the most efficient photosensitiser.
机译：描述了对新系列阳离子卟啉 - 萜烯衍生物的简单进入。获得所需中性前体作为主要产品的关键步骤涉及Krohnke型方法。该方法还允许各个苯并卟啉和卟啉 - 查耳酮型衍生物的分离，并且在一种情况下一个新的2-（2,4-三联吡啶-6-基） - 卟啉。在适当的烷基碘的存在下进行吡啶基的季铵化，得到优异的产率。所有新的缀合物都完全表征，发现阳离子异构体可以通过ESI-MS有效地分化，因为它们的行为可以通过质谱法集中研究。新的甲基化的阳离子卟啉 - 三联吡啶衍生物证明产生单线态氧和它们的效力，以photoinactivate生物发光革兰氏阴性大肠杆菌进行评价的能力。使用最有效的光敏性仪获得增强生物发光信号，最高可达5.4个对数。

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  • 来源
    《RSC Advances》 |2016年第112期|共12页
  • 作者

    Moura Nuno M. M.; Ramos Catarina I. V.; Linhares Ines; Santos Sergio M.; Faustino M. Amparo F.; Almeida Adelaide; Cavaleiro Jose A. S.; Amado Francisco M. L.; Lodeiro Carlos; Neves M. Graca P. M. S.;

  • 作者单位

    Univ Aveiro Dept Chem QOPNA Organ Chem Lab P-3810193 Aveiro Portugal;

    Univ Aveiro Dept Chem QOPNA Mass Spectrometry Lab P-3810193 Aveiro Portugal;

    Univ Aveiro CESAM Dept Biol P-3810193 Aveiro Portugal;

    Univ Aveiro Dept Chem CICECO P-3810193 Aveiro Portugal;

    Univ Aveiro Dept Chem QOPNA Organ Chem Lab P-3810193 Aveiro Portugal;

    Univ Aveiro CESAM Dept Biol P-3810193 Aveiro Portugal;

    Univ Aveiro Dept Chem QOPNA Organ Chem Lab P-3810193 Aveiro Portugal;

    Univ Aveiro Dept Chem QOPNA Mass Spectrometry Lab P-3810193 Aveiro Portugal;

    Univ Nova Lisboa Fac Ciencias &

    Tecnol Dept Quim BIOSCOPE Res Team UCIBIO REQUIMTE P-2829516 Caparica Portugal;

    Univ Aveiro Dept Chem QOPNA Organ Chem Lab P-3810193 Aveiro Portugal;

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  • 正文语种 eng
  • 中图分类 化学;
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