ExTzBox: A Glowing Cyclophane for Live-Cell Imaging

Journal of the American Chemical Society
Indranil RoyJ Fraser Stoddart

Abstract

The ideal fluorescent probe for live-cell imaging is bright and non-cytotoxic and can be delivered easily into the living cells in an efficient manner. The design of synthetic fluorophores having all three of these properties, however, has proved to be challenging. Here, we introduce a simple, yet effective, strategy based on well-established chemistry for designing a new class of fluorescent probes for live-cell imaging. A box-like hybrid cyclophane, namely ExTzBox·4X (6·4X, X = PF6-, Cl-), has been synthesized by connecting an extended viologen (ExBIPY) and a dipyridyl thiazolothiazole (TzBIPY) unit in an end-to-end fashion with two p-xylylene linkers. Photophysical studies show that 6·4Cl has a quantum yield ΦF = 1.00. Furthermore, unlike its ExBIPY2+ and TzBIPY2+ building units, 6·4Cl is non-cytotoxic to RAW 264.7 macrophages, even with a loading concentration as high as 100 μM, presumably on account of its rigid box-like structure which prevents its intercalation into DNA and may inhibit other interactions with it. After gaining an understanding of the toxicity profile of 6·4Cl, we employed it in live-cell imaging. Confocal microscopy has demonstrated that 64+ is taken up by the RAW 264.7 macrophages, allowing the cells to...Continue Reading

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Citations

Aug 15, 2018·Chemistry : a European Journal·Natasza SpruttaLechosław Latos-Grażyński
Jan 29, 2020·Acta Physiologica·Adrienne M AssmusLinda J Mullins
Jun 12, 2019·Chemical Science·Tianyu JiaoHao Li
Mar 28, 2020·Chemical Communications : Chem Comm·Tian TianWenping Hu
Mar 10, 2020·Chemical Communications : Chem Comm·Jie YuBen Zhong Tang
Nov 21, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Giovanni F CaramoriSérgio E Galembeck
Jan 26, 2021·Angewandte Chemie·Stephan HagspielHolger Braunschweig
Mar 30, 2021·Journal of the American Chemical Society·Indranil RoyJ Fraser Stoddart
Apr 3, 2020·Journal of the American Chemical Society·Amine GarciJ Fraser Stoddart
Sep 1, 2020·Journal of the American Chemical Society·Indranil RoyJ Fraser Stoddart
Sep 29, 2018·Journal of the American Chemical Society·Yi ShiJ Fraser Stoddart
Oct 4, 2019·Journal of the American Chemical Society·M Mustafa CetinJ Fraser Stoddart
Oct 30, 2019·Journal of the American Chemical Society·Nickolas A SayresmithMichael G Walter
Nov 13, 2020·Journal of the American Chemical Society·Xiao-Yang ChenJ Fraser Stoddart
Jul 2, 2019·Journal of the American Chemical Society·Indranil RoyJ Fraser Stoddart
Sep 16, 2021·Physical Chemistry Chemical Physics : PCCP·Tomomi Shimazaki, Masanori Tachikawa

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