4.8 Article

An Ultrasensitive Cyclization-Based Fluorescent Probe for Imaging Native HOBr in Live Cells and Zebrafish

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 41, Pages 12751-12754

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201606285

Keywords

bioimaging; cyclization reactions; fluorescent probes; hypobromous acid

Funding

  1. 973 Program [2013CB933800]
  2. National Natural Science Foundation of China [21535004, 21227005, 21390411, 21275092, 21575081, 21507075]

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Bromine has been reported recently as being the 28(th) essential element for human health. HOBr, which is generated invivo from bromide, is a required factor in the formation of sulfilimine crosslinks in collagenIV. However, to date, no method for the specific detection of native HOBr invivo has been reported. Herein, we develop a simple small molecular probe for imaging HOBr based on a specific cyclization catalyzed by HOBr. The probe can be easily synthesized in high yield through a Suzuki cross-coupling reaction. The probe exhibits ultrahigh sensitivity at the picomole level, in addition to specificity for HOBr and real-time response. Importantly, without Br- stimulation, this probe reports native HOBr levels in HepG2 cells. Thus, the probe is a promising new tool for imaging endogenous HOBr and may provide a means for finding new physiological functions of HOBr in living organisms.

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