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Design and Synthesis of a BODIPY‐Tetrazole Based “Off‐On” in‐Cell Fluorescence Reporter of Hydrogen Peroxide
Author(s) -
An Peng,
Lewandowski Tracey M.,
Lin Qing
Publication year - 2018
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201700656
Subject(s) - bodipy , tetrazole , hydrogen peroxide , chemistry , fluorescence , pyrazoline , bioorthogonal chemistry , hela , photochemistry , reactivity (psychology) , combinatorial chemistry , in vitro , stereochemistry , organic chemistry , biochemistry , click chemistry , medicine , physics , alternative medicine , pathology , quantum mechanics
BODIPY‐linked bithiophene‐tetrazoles were designed and synthesized for bioorthogonal photoclick reactions in vitro and in vivo. The reactivity of these tetrazoles toward dimethyl fumarate was found to depend on the BODIPY attachment site, with the meta ‐linked BODIPY–tetrazole being the most reactive. The resulting pyrazoline cycloadduct showed drastically reduced BODIPY fluorescence. However, BODIPY fluorescence recovered after treatment with hydrogen peroxide. This turn‐on effect was attributed to conversion from the pyrazoline to a pyrazole. Finally, we showed that this unique BODIPY–tetrazole off–on fluorescence probe can be used to detect hydrogen peroxide inside HeLa cells.