Boronate-Based Fluorescence Probes for the Detection of Hydrogen Peroxide

Emma V. Lampard, Adam C. Sedgwick, Xiaolong Sun, Katherine L. Filer, Samantha C. Hewins, Gyoungmi Kim, Juyoung Yoon, Steven D. Bull, Tony D. James

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

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.

Original languageEnglish
Pages (from-to)262-265
Number of pages4
JournalChemistryOpen
Volume7
Issue number3
DOIs
StatePublished - Mar 2018

Keywords

  • boronic acids
  • diagnostics
  • fluorescent probes
  • HO
  • intramolecular charge transfer (ICT)

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