The development of 1,3-diphenylisobenzofuran as a highly selective probe for the detection and quantitative determination of hydrogen peroxide

Krzysztof Żamojć , Magdalena Zdrowowicz , Paweł Błażej Rudnicki-Velasquez , Karol Krzymiński , Bartłomiej Zaborowski , Paweł Niedziałkowski , Dagmara Jacewicz , Lech Chmurzyński

Abstract

1,3-Diphenylisobenzofuran (DPBF) has been developed as a selective probe for the detection and quantitative determination of hydrogen peroxide in samples containing different reactive nitrogen and oxygen species (RNOS). DPBF is a fluorescent probe which, for almost 20 years, was believed to react in a highly specific manner toward some reactive oxygen species (ROS) such as singlet oxygen and hydroxy, alkyloxy or alkylperoxy radicals. Under the action of these individuals DPBF has been rapidly transformed to 1,2-dibenzoylbenzene (DBB). In order to check if DPBF can act as a unique indicator of the total amount of different RNOS, as well as oxidative stress caused by an overproduction of these individuals, a series of experiments was carried out, in which DPBF reacted with peroxynitrite anion, superoxide anion, hydrogen peroxide, hypochlorite anion, and anions commonly present under biological conditions, namely nitrite and nitrate. In all cases, except for hydrogen peroxide, the product of the reaction is DBB. Only under the action of H2O2 9-hydroxyanthracen-10(9H)-one (oxanthrone) is formed. This product has been identified with the use of fluorescence spectroscopy, NMR spectroscopy, high performance liquid chromatography coupled with mass spectrometry, infrared spectroscopy, elemental analysis, and cyclic voltammetry (CV). A linear relationship was found between a decrease in the fluorescence intensity of DPBF and the concentration of hydrogen peroxide in the range of concentrations of 0.196–3.941 mM. DPBF responds to hydrogen peroxide in a very specific way with the limits of detection and quantitation of 88 and 122.8 μM, respectively. The kinetics of the reaction between DBBF and H2O2 was also studied.
Author Krzysztof Żamojć (FCh / DGICh / LPCC)
Krzysztof Żamojć,,
- Laboratory of Physicochemistry of Coordination Complexes
, Magdalena Zdrowowicz (FCh / DPCh / LBS)
Magdalena Zdrowowicz,,
- Laboratory of Biological Sensitizers
, Paweł Błażej Rudnicki-Velasquez (FCh / DPCh / LLR)
Paweł Błażej Rudnicki-Velasquez,,
- Laboratory of Luminescence Research
, Karol Krzymiński (FCh / DPCh / LLR)
Karol Krzymiński,,
- Laboratory of Luminescence Research
, Bartłomiej Zaborowski (FCh / DTCh / LSP)
Bartłomiej Zaborowski,,
- Laboratory of Simulation of Polymers
, Paweł Niedziałkowski (FCh / DACh / LSCh)
Paweł Niedziałkowski,,
- Laboratory of Supramolecular Chemistry
, Dagmara Jacewicz (FCh / DGICh / LPCC)
Dagmara Jacewicz,,
- Laboratory of Physicochemistry of Coordination Complexes
, Lech Chmurzyński (FCh / DGICh / LPCC)
Lech Chmurzyński,,
- Laboratory of Physicochemistry of Coordination Complexes
Journal seriesFree Radical Research, ISSN 1071-5762, (A 25 pkt)
Issue year2017
Vol51
No1
Pages38-46
Publication size in sheets0.5
Keywords in English1,3-diphenylisobenzofuran, hydrogen peroxide, fluorescence spectroscopy, high performance liquid chromatography coupled with mass spectrometry, selectivity, limit of detection and quantitation
DOIDOI:10.1080/10715762.2016.1262541
Languageen angielski
Score (nominal)25
ScoreMinisterial score = 25.0, 20-12-2017, ArticleFromJournal
Ministerial score (2013-2016) = 25.0, 20-12-2017, ArticleFromJournal
Publication indicators WoS Impact Factor: 2016 = 3.188 (2) - 2016=3.017 (5)
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