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.

Boronic acids as building blocks for the construction of therapeutically useful bioconjugates

“…Similar methodologies [63][64][65][66][67][68] were developed by other groups using different fluorescent dyes. [69][70][71][72][73][74][75][76][77][78] Following the same rationale, various self-immolative linkers triggered by H 2 O 2 were reported. Cohen and co-workers published various examples of BA-based linkers in which the conversion of the BA into phenol triggers a selfimmolative cascade (Fig.…”

Styryl Group, a Friend or Foe in Medicinal Chemistry

“…[185] The boronate ester moiety-containing fluorescent probe 212 detects hydrogen peroxide in buffer solutions (Figure 34a). [186] Hydrogen sulfide (H 2 S) is a cytotoxic biomolecule whose accumulation, even in trace quantities in the biological system, is associated with various pathological events. The styryl-linked isoxazole fluorescent probes 214-217 quantitatively detects H 2 S via reducing a nitro group into the amino group in an aqueous sodium sulfide medium (Figure 34b).…”

Cobalt Phosphide (Co2P) with Notable Electrocatalytic Activity Designed for Sensitive and Selective Enzymeless Bioanalysis of Hydrogen Peroxide

“…Developing accurate, sensitive, rapid and selective methods to detect the concentration of H 2 O 2 , a normal oxidative stress biomarker, will be undoubtedly beneficial to the early diagnosis. Up to now, a host of analytical methods such as spectroscopy [ 6 ], colorimetry [ 7 ], fluorescence [ 8 , 9 ] and electrochemical methods [ 10 – 12 ] have been applied in H 2 O 2 determination. Electrochemical method, especially amperometric test is gradually becoming one of the most simple and effective detection methods for H 2 O 2 biological analysis among diverse sensing methods due to its advantages such as high sensitivity, outstanding selectivity and low cost.…”