Biological hydrogen peroxide detection with aryl boronate and benzil BODIPY-based fluorescent probes

•First study comparing the optical and sensing properties between the two reactive architectures against hydrogen peroxide.•Two new probes, peroxy BODIPY-1 (PB1) and nitrobenzoyl-BODIPY (NbzB) were developed.•Sensing properties such as biocompatibility, cell permeability, selectivity and photostabil...

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Published inSensors and actuators. B, Chemical Vol. 262; pp. 750 - 757
Main Authors Purdey, Malcolm S., McLennan, Hanna J., Sutton-McDowall, Melanie L., Drumm, Daniel W., Zhang, Xiaozhou, Capon, Patrick K., Heng, Sabrina, Thompson, Jeremy G., Abell, Andrew D.
Format Journal Article
LanguageEnglish
Published Lausanne Elsevier B.V 01.06.2018
Elsevier Science Ltd
Subjects
Aromatic compounds
Benzil
BODIPY
Boron
Cattle
Fluorescence
Fluorescent indicators
Fluorescent sensor
Hydrogen peroxide
Oxidative stress
Reactive oxygen species
Selectivity
Studies
Fluorescent sensor
BODIPY
Reactive oxygen species
Hydrogen peroxide
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Summary:•First study comparing the optical and sensing properties between the two reactive architectures against hydrogen peroxide.•Two new probes, peroxy BODIPY-1 (PB1) and nitrobenzoyl-BODIPY (NbzB) were developed.•Sensing properties such as biocompatibility, cell permeability, selectivity and photostability were detailed.•Sensing experiments in bovine oocytes were carried out as the first step towards detecting H2O2 associated with an increased incidence of DNA damage in developing embryos. The detection of hydrogen peroxide (H2O2) using fluorescent probes is critical to the study of oxidative stress in biological environments. Two important sensing architectures for detecting H2O2, aryl boronates and benzils, are compared here using novel boron-dipyrromethene (BODIPY) fluorescent probes. The aryl boronate PeroxyBODIPY-1 (PB1) and benzil-based nitrobenzoylBODIPY (NbzB) were synthesised from a common BODIPY intermediate in order to compare sensitivity and selectivity to H2O2. The aryl boronate PB1 gives the highest change in fluorescence on reaction with H2O2 while the benzil NbzB exhibits exclusive selectivity for H2O2 over other reactive oxygen species (ROS). Both proved to be cell-permeable, with PB1 being able to detect H2O2 in denuded bovine oocytes. The strengths of these aryl boronate and benzil probes can now be exploited concurrently to elucidate biological mechanisms of H2O2 production and oxidative stress.
ISSN:0925-4005
1873-3077
DOI:10.1016/j.snb.2018.01.198