Hymecromone naphthoquinone ethers as probes for hydrogen sulfide detection. (December 2021)

• Record Type: Journal Article
• Authors: Słowiński, Daniel; Świerczyńska, Małgorzata; Grzelakowska, Aleksandra; Szala, Marcin; Kolińska, Jolanta; Romański, Jarosław; Podsiadły, Radosław
• Is Part Of: Dyes and pigments. Volume 196(2022)
• Publication Date: 2021-12
• Subjects: Dual-mode detections -- Coumarin-derived probe -- Hydrogen sulfide -- Fluorescent probe -- Colorimetric probe; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2021.109765
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: Hydrogen sulfide (H2 S), as one of the important gasotransmitters, plays an essential role in a many physiological and pathological processes. Commonly used methods for real-time detection and quantification of H2 S are rather complicated. This report presents a simple fluorescence and colorimetry dual-mode assay based on ethers (Nq-Cm and Nq-2Cm ) derived from hymecromone (7-hydroxy-4-methylcoumarin, Cm ) and naphthoquinone (Nq ). In these compounds an electron-deficient naphthoquinone unit was used as a suitable reagent for nucleophilic aromatic substitution (SN Ar) reaction. Thiolysis of Nq-Cm and Nq-2Cm at physiological pH releases Cm and causes an significant fluorescence enhancement at 448 nm (with excitation at 320 nm). At the same time, the resulting naphthoquinone derivative Nq-2SH causes the solution a purple color, which allows naked-eye detection. Thus Nq-Cm and Nq-2Cm are colorimetrically selective for H2 S. The efficacy of the Nq-Cm and Nq-2Cm were demonstrated in buffer with associated submicromolar detection limit as low as 130 nM and 150 nM, respectively. Presented results suggest that both probes are excellent quantitative detection tool for H2 S. Graphical abstract: Image 1 Highlights: A simple fluorescent probes (Nq-Cm and Nq-2Cm ) based on the coumarin-naphthoquinone framework were developed. Electron deficient naphthoquinone unit was selected for the first time to promote the nucleophilic substitution reaction. The probes show good stability, high sensitivity, fast response to H2 S and remarkable fluorescent turn on enhancement. Mono- and bis-hymecromone naphthoquinone ethers produce one and two equivalents of coumarin, respectively. The probes could be also used to colorimetric detection H2 S and distinguish between common biothiols (L-Cys, GSH, NAC).