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 journalArticle

8 Citations (Scopus)

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 (H 2O 2). DSTBPin and MSTBPin displayed an “Off–On” fluorescence response towards H 2O 2, owing to the loss of the intramolecular charge transfer (ICT) excited state. Whereas, CSTBPin displayed a decrease in fluorescence intensity in the presence of H 2O 2 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 H 2O 2 (>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
Early online date26 Jan 2018
DOIs
Publication statusPublished - 1 Mar 2018

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Lampard, E. V., Sedgwick, A. C., Sun, X., Filer, K. L., Hewins, S. C., Kim, G., ... James, T. D. (2018). Boronate-Based Fluorescence Probes for the Detection of Hydrogen Peroxide. ChemistryOpen, 7(3), 262-265. https://doi.org/10.1002/open.201700189

Boronate-Based Fluorescence Probes for the Detection of Hydrogen Peroxide. / Lampard, Emma V.; Sedgwick, Adam C.; Sun, Xiaolong; Filer, Katherine L.; Hewins, Samantha C.; Kim, Gyoungmi; Yoon, Juyoung; Bull, Steven D.; James, Tony D.

In: ChemistryOpen, Vol. 7, No. 3, 01.03.2018, p. 262-265.

Research output: Contribution to journalArticle

Lampard, EV, Sedgwick, AC, Sun, X, Filer, KL, Hewins, SC, Kim, G, Yoon, J, Bull, SD & James, TD 2018, 'Boronate-Based Fluorescence Probes for the Detection of Hydrogen Peroxide', ChemistryOpen, vol. 7, no. 3, pp. 262-265. https://doi.org/10.1002/open.201700189
Lampard EV, Sedgwick AC, Sun X, Filer KL, Hewins SC, Kim G et al. Boronate-Based Fluorescence Probes for the Detection of Hydrogen Peroxide. ChemistryOpen. 2018 Mar 1;7(3):262-265. https://doi.org/10.1002/open.201700189
Lampard, Emma V. ; Sedgwick, Adam C. ; Sun, Xiaolong ; Filer, Katherine L. ; Hewins, Samantha C. ; Kim, Gyoungmi ; Yoon, Juyoung ; Bull, Steven D. ; James, Tony D. / Boronate-Based Fluorescence Probes for the Detection of Hydrogen Peroxide. In: ChemistryOpen. 2018 ; Vol. 7, No. 3. pp. 262-265.
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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 (H 2O 2). DSTBPin and MSTBPin displayed an “Off–On” fluorescence response towards H 2O 2, owing to the loss of the intramolecular charge transfer (ICT) excited state. Whereas, CSTBPin displayed a decrease in fluorescence intensity in the presence of H 2O 2 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 H 2O 2 (>3 mm) to produce noticeable changes in fluorescence intensity and, therefore, no change in fluorescence was observed in the cell imaging experiments.",
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AU - Hewins, Samantha C.

AU - Kim, Gyoungmi

AU - Yoon, Juyoung

AU - Bull, Steven D.

AU - James, Tony D.

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AB - 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 (H 2O 2). DSTBPin and MSTBPin displayed an “Off–On” fluorescence response towards H 2O 2, owing to the loss of the intramolecular charge transfer (ICT) excited state. Whereas, CSTBPin displayed a decrease in fluorescence intensity in the presence of H 2O 2 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 H 2O 2 (>3 mm) to produce noticeable changes in fluorescence intensity and, therefore, no change in fluorescence was observed in the cell imaging experiments.

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