A red-emitting ratiometric fluorescent probe with large Stokes shift and emission peak shift for imaging hypochlorous acid in living cells and zebrafish. (January 2022)

• Record Type: Journal Article
• Authors: Zhang, Yan; Yang, Haiyan; Li, Mingxin; Gong, Shuai; Song, Jie; Wang, Zhonglong; Wang, Shifa
• Is Part Of: Dyes and pigments. Volume 197(2022)
• Publication Date: 2022-01
• Subjects: Nopinone -- Ratiometric probe -- HClO -- Bioimaging; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2021.109861
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: Hypochlorous acid (HClO) with strong oxidizing property holds an essential role in the resistance against offensive microorganisms in the inherent immune system of living organism. However, an excess of HClO can bring about oxidative stress and cellular damage, which are associated with many diseases. Herein, a novel nopinone-based ratiometric fluorescent probe BIDID (2-(4-(5, 5-dimethyl-4, 5, 6, 7-tetr-ahydro-1 H -4, 6-methanobenzo[ d ]imidazole-2-yl)benzylidene)-1 H -indene-1, 3(2 H )-dione) was rationally devised to track exogenous and endogenously generated HClO in vitro and vivo. BIDID itself featured an extremely large Stokes shift (241 nm) and exhibited a bright red emission at 641 nm. Upon treating with HClO, the CC bond of BIDID was exclusively broken, thereby resulting in the generation of compound BID (4-(5, 5-dimethyl-4, 5, 6, 7-tetrahydro-1 H -4, 6-methanobenzo[ d ]imidazole-2-yl)benzalde-hyde) with a remarkably hypochromatic-shifted emission at 501 nm. As expected, this probe was highly responsive to HClO with good selectivity, superior sensitivity, low limit of detection (13.2 nM), rapid response (within 0.5 min), and wide pH range (6–12). What's more, BIDID was applicable for validation of HClO on solid platform and in real water samples. Additionally, the confocal fluorescent images of HClO in vitro and in vivo demonstrated that BIDID can function as a reliable tool for studying HClO-related physiological and pathological processes. Graphical abstract: Image 1 Highlights: A novel ratiometric fluorescent probe BIDID with a large Stokes shift was constructed for tracking HClO from nopinone. The probe BIDID exhibited a remarkable emission peak shift in the detection of HClO. The probe BIDID could selectively sense HClO with low detection limit and fast response time. The probe BIDID was applied for monitoring exogenous and endogenous HClO in living cells and zebrafish.