title: The development of 1,3-diphenylisobenzofuran as a highly selective probe for the detection and quantitative determination of hydrogen peroxide.
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 H2O29-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 H2O2was also studied.
authors.affiliation: a Faculty of Chemistry , University of Gdansk , Gdansk , Poland.
authors.forename: Krzysztof
authors.initials: K
authors.lastname: Żamojć
authors.affiliation: a Faculty of Chemistry , University of Gdansk , Gdansk , Poland.
authors.forename: Magdalena
authors.initials: M
authors.lastname: Zdrowowicz
authors.affiliation: a Faculty of Chemistry , University of Gdansk , Gdansk , Poland.
authors.forename: Paweł Błażej
authors.initials: PB
authors.lastname: Rudnicki-Velasquez
authors.affiliation: a Faculty of Chemistry , University of Gdansk , Gdansk , Poland.
authors.forename: Karol
authors.initials: K
authors.lastname: Krzymiński
authors.affiliation: a Faculty of Chemistry , University of Gdansk , Gdansk , Poland.
authors.forename: Bartłomiej
authors.initials: B
authors.lastname: Zaborowski
authors.affiliation: a Faculty of Chemistry , University of Gdansk , Gdansk , Poland.
authors.forename: Paweł
authors.initials: P
authors.lastname: Niedziałkowski
authors.affiliation: a Faculty of Chemistry , University of Gdansk , Gdansk , Poland.
authors.forename: Dagmara
authors.initials: D
authors.lastname: Jacewicz
authors.affiliation: a Faculty of Chemistry , University of Gdansk , Gdansk , Poland.
authors.forename: Lech
authors.initials: L
authors.lastname: Chmurzyński
mesh_terms: D001572:Benzofurans / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D005456:Fluorescent Dyes / Q000737:chemistry*; D006861:Hydrogen Peroxide / Q000032:analysis* / Q000737:chemistry; D057230:Limit of Detection; D026361:Reactive Nitrogen Species / Q000737:chemistry
chemical_list: D001572:Benzofurans; D005456:Fluorescent Dyes; D026361:Reactive Nitrogen Species; C011238:1,3-diphenylisobenzofuran; D006861:Hydrogen Peroxide
keywords: 1,3-diphenylisobenzofuran; fluorescence spectroscopy; high performance liquid chromatography coupled with mass spectrometry; hydrogen peroxide; limit of detection and quantitation; selectivity