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A novel coumarin-based fluorescent probe with fine selectivity and sensitivity for hypochlorite and its application in cell imaging

Jin, Lei, Tan, Xiaoxue, Dai, Lihui, Zhao, Cong, Wang, Wenling, Wang, Qingming
Talanta 2019 v.202 pp. 190-197
anions, buffers, coumarin, density functional theory, detection limit, emissions factor, ethanol, fluorescence, fluorescent dyes, hydrogen peroxide, hydroxyl radicals, hypochlorites, image analysis, metal ions, oxidation, pH, singlet oxygen
It is necessary to develop simple and highly sensitive methods for the detection of hypochlorous acid (HOCl)/hypochlorite (ClO−) to ravel its relationship with disease. In this paper, a novel bio-compatible fluorescent (Z)-8-(hydrazonomethyl)-7-hydroxy-4-methyl-2H-chromen-2-one (probe 1b) based on coumarin was synthesized and used for detecting ClO− in PBS buffer (pH = 7.2, 10 mM, 60% C2H5OH). Probe 1b showed a remarkable fluorescence change from yellow to blue with the limit of detection as low as 2.4 × 10−9 M−1 when ClO− was added. The coexisted anions, metal ions and reactive oxygen species (•OH, 1O2, H2O2, KO2) showed any competitiveness towards ClO−. In response to ClO−, the fluorescence emission intensity of probe 1b was obviously enhanced within 20 s. The mechanism was confirmed by the ESI - MS and density functional theory calculations (DFT) to reveal that the coumarin lactone bonds C − O was cleavaged by oxidation of ClO−. What's more, probe 1b could be used in practical water samples and showed well recovery. Additionally, the cell imaging experiment was demonstrated that probe 1b could be effectively exploited to imaging exogenous ClO− in vitro.