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The Remarkable Effect of Halogen Substitution on the Membrane Transport of Fluorescent Molecules in Living Cells
Angewandte Chemie International Edition ( IF 16.6 ) Pub Date : 2018-06-20 , DOI: 10.1002/anie.201804128
Harinarayana Ungati 1 , Vijayakumar Govindaraj 1 , Govindasamy Mugesh 1
Affiliation  

Small‐molecule‐based fluorescent probes have become important tools in biology for sensing and imaging applications. However, the biological applications of many of the fluorescent molecules are hampered by low cellular uptake and high toxicity. In this paper, we show for the first time that the introduction of halogen atoms enhances the cellular uptake of fluorescent molecules and the nature of halogen atoms plays a crucial role in the plasma membrane transport in mammalian cells. The remarkably higher uptake of iodinated compounds compared to that of their chloro or bromo analogues suggests that the strong halogen bonding ability of iodine atoms may play an important role in the membrane transport. This study provides a novel strategy for the transport of fluorescent molecules across the plasma membrane in living cells.

中文翻译:

卤素取代对活细胞内荧光分子膜转运的显着影响

基于小分子的荧光探针已成为生物学中传感和成像应用的重要工具。但是,许多荧光分子的生物学应用受到低细胞摄取和高毒性的阻碍。在本文中,我们首次表明引入卤素原子可增强荧光分子的细胞吸收,并且卤素原子的性质在哺乳动物细胞的质膜运输中起着至关重要的作用。与它们的氯代或溴代类似物相比,碘代化合物的摄取显着更高,这表明碘原子的强卤素键合能力可能在膜运输中起重要作用。这项研究为活细胞中荧光分子跨质膜的运输提供了一种新的策略。
更新日期:2018-06-20
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