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Boronate-Based Fluorescence Probes for the Detection of Hydrogen Peroxide.


ABSTRACT: In this work, we synthesized a series of boronate ester fluorescence probes (E)-4,4,5,5-tetramethyl-2-(4-styrylphenyl)-1,3,2-dioxaborolane (STBPin), (E)-N,N-dimethyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)styryl)aniline (DSTBPin), (E)-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)styryl)benzonitrile (CSTBPin), (E)-2-(4-(4-methoxystyryl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (MSTBPin), (E)-N,N-dimethyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)styryl)naphthalen-1-amine (NDSTBPin), and N,N-dimethyl-4-(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)oxazol-5-yl)aniline (DAPOX-BPin) for the detection of hydrogen peroxide (H2O2). DSTBPin and MSTBPin displayed an "Off-On" fluorescence response towards H2O2, owing to the loss of the intramolecular charge transfer (ICT) excited state. Whereas, CSTBPin displayed a decrease in fluorescence intensity in the presence of H2O2 owing to the introduction of an ICT excited state. STBPin, on the other hand, produced a small fluorescence decrease, indicating the importance of an electron-withdrawing or electron-donating group in these systems. Unfortunately, the longer wavelength probe, NDSTBPin, displayed a decrease in fluorescence intensity. Oxazole-based probe DAPOX-BPin produced a "turn-on" response. Regrettably, DAPOX-BPin required large concentrations of H2O2 (>3?mm) to produce noticeable changes in fluorescence intensity and, therefore, no change in fluorescence was observed in the cell imaging experiments.

SUBMITTER: Lampard EV 

PROVIDER: S-EPMC5838387 | biostudies-literature | 2018 Mar

REPOSITORIES: biostudies-literature

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Boronate-Based Fluorescence Probes for the Detection of Hydrogen Peroxide.

Lampard Emma V EV   Sedgwick Adam C AC   Sun Xiaolong X   Filer Katherine L KL   Hewins Samantha C SC   Kim Gyoungmi G   Yoon Juyoung J   Bull Steven D SD   James Tony D TD  

ChemistryOpen 20180126 3


In this work, we synthesized a series of boronate ester fluorescence probes (<i>E</i>)-4,4,5,5-tetramethyl-2-(4-styrylphenyl)-1,3,2-dioxaborolane (<b>STBPin)</b>, (<i>E</i>)-<i>N</i>,<i>N</i>-dimethyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)styryl)aniline (<b>DSTBPin)</b>, (<i>E</i>)-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)styryl)benzonitrile (<b>CSTBPin)</b>, (<i>E</i>)-2-(4-(4-methoxystyryl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (<b>MSTBPin)</b>, (<i>E</i>)-<i>N</i  ...[more]

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