Rapid-response and highly sensitive boronate derivative-based fluorescence probe for detecting H2O2 in living cells
- Rapid-response and highly sensitive boronate derivative-based fluorescence probe for detecting H2O2 in living cells
- 이강봉; 이연희; 남윤식; 김병찬; 한상수; Sung Jin Pai; Muthusamy Selvaraj; Kanagaraj Rajalakshmi
- Highly Sensitive Boronate Derivative; Fluorescence Probe for Detecting H2O2; Triphenylimidazoleoxadiazolephenyl boronate
- Issue Date
- Journal of Analytical Methods in Chemistry
- VOL 2019, NO 5174764-12
- Intracellular H2O2 monitoring is important and has driven researchers to pursue advancements for the rapid identification of H2O2, since H2O2 is short-lived in cell lines. An arylboronate derivative has been investigated as a chemospecific fluorescence recognition agent for H2O2. Triphenylimidazoleoxadiazolephenyl (TPIOP) boronate was contrived as a novel candidate for the rapid and sensitive recognition of H2O2. .e probe was conjugated using the TPIOP functional group acting as an excellent fluorescent enhancer. .e TPIOP group stimulated the polarization of C– B bond due to its extended π-conjugation, which included heteroatoms, and induced the production of rapid signal because of the highly polar C– B bond along with the corresponding boronate unit. While H2O2 reacts with TPIOP boronate, its nucleophilic addition to the boron generates a charged tetrahedral boronate complex, and then the C– B bond migrates toward one of the electrophilic peroxide oxygen atoms. .e resulting boronate ester is then hydrolyzed by water into a phenol, which significantly enhances fluorescence through aggregationinduced emission. .e TPIOP boronate probe responded to H2O2 rapidly, within 2 min, and exhibited high sensitivity with a limit of detection of 8nM and a 1000-fold selectivity in the presence of other reactive oxygen species. .erefore, the developed TPIOP boronate chemodosimeter was successfully utilized to visualize and quantify intracellular H2O2 from human breast cancer (MCF-7) cells, as well as gaseous and aqueous H2O2 from environmental samples using Whatman paper strips coated with TPIOP boronate.
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