The Remarkable Effect of Halogen Substitution on the Membrane Transport of Fluorescent Molecules in Living Cells

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 int...

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Bibliographic Details
Published in:Angewandte Chemie 2018-07, Vol.130 (29), p.9127-9131
Main Authors: Ungati, Harinarayana, Govindaraj, Vijayakumar, Mugesh, Govindasamy
Format: Article
Language:English
Subjects:
Aufnahme in Zellen
Bonding strength
Cells (biology)
Chemistry
Fluorescent indicators
Fluoreszierende Moleküle
Halogene
Iodine
Mammalian cells
MCT8-Transporter
Molecular chains
Schilddrüsenhormone
Toxicity
Transport
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Summary: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. Halogen als Strategem: Durch Einführung von Halogensubstituenten in fluoreszierende Moleküle werden diese besser in Zellen aufgenommen. Darauf beruht eine Strategie zum Transport organischer Moleküle durch die Plasmamembran lebender Zellen.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201804128