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

Angewandte Chemie
Harinarayana UngatiGovindasamy Mugesh

Abstract

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.

References

Jul 23, 2003·The Journal of Biological Chemistry·Edith C H FriesemaTheo J Visser
Apr 15, 2004·The Journal of Biological Chemistry·Therese EneqvistA Elisabeth Sauer-Eriksson
Oct 19, 2005·Journal of Computer-aided Molecular Design·Igor V TetkoVolodymyr V Prokopenko
Oct 3, 2006·Journal of Molecular Modeling·Peter PolitzerJane S Murray
Jul 25, 2008·Angewandte Chemie·Pierangelo MetrangoloGiancarlo Terraneo
Jun 9, 2009·Endocrine Reviews·Evanthia Diamanti-KandarakisAndrea C Gore
Mar 17, 2012·Angewandte Chemie·Michael Schäferling
Apr 3, 2012·Expert Opinion on Drug Discovery·Yunxiang LuWeiliang Zhu
Apr 4, 2013·Accounts of Chemical Research·Andreas Vargas JentzschStefan Matile
Apr 4, 2014·Topics in Current Chemistry·Andreas Vargas Jentzsch, Stefan Matile
Sep 24, 2014·Accounts of Chemical Research·Sudesh T ManjareDavid G Churchill
Oct 30, 2014·Angewandte Chemie·Joris BeldMichael D Burkart
May 20, 2015·Journal of the American Chemical Society·Jun Jacob HuDan Yang
May 27, 2016·Angewandte Chemie·Santanu MondalGovindasamy Mugesh
Nov 20, 2016·Annual Review of Physiology·Elizabeth A SpechtAmy E Palmer
May 2, 2017·Journal of the American Chemical Society·Li WuDaniel T Chiu
May 10, 2017·Proceedings of the National Academy of Sciences of the United States of America·Qian ChenZhuang Liu
May 22, 2017·Current Opinion in Chemical Biology·Kevin J BruemmerChristopher J Chang
Jun 10, 2017·Chemical Reviews·Wenhu ZhouJuewen Liu
Jun 24, 2017·Nature Reviews. Cancer·Miles A Miller, Ralph Weissleder
Nov 16, 2017·Proceedings of the National Academy of Sciences of the United States of America·Allegra T AronChristopher J Chang
Dec 25, 2017·Current Opinion in Chemical Biology·Ziyang HaoPeng R Chen

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Citations

Jan 4, 2019·Chemistry : a European Journal·Harinarayana UngatiGovindasamy Mugesh
Feb 6, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Yunxi YeJinlou Gu
May 28, 2019·Expert Opinion on Drug Discovery·Paulo J CostaDiogo Vila-Viçosa
Apr 17, 2020·Chemical Communications : Chem Comm·Gilles BergerFranck Meyer
Jun 20, 2019·Chemistry : a European Journal·Vijayakumar GovindarajGovindasamy Mugesh
Mar 10, 2021·Journal of the American Chemical Society·Rafael Santana NunesPaulo J Costa
Aug 1, 2019·The Journal of Physical Chemistry. a·Sophia Bazzi, Robin Santra

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