Rhodol Derivatives as Selective Fluorescent Probes for the Detection of Hg(II) Ions and the Bioimaging of Hypochlorous Acid.

Rhodol Derivatives as Selective Fluorescent Probes for the Detection of Hg(II) Ions and the Bioimaging of Hypochlorous Acid.
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Rhodol 衍生物作为选择性荧光探针用于检测 Hg-II 离子和次氯酸的生物成像

DOI:
10.1002/open.201700154
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发表时间:
2018-03
期刊:
影响因子:
2.3
通讯作者:
Wong KM
Wong KM
中科院分区:
化学3区
文献类型:
--
作者:
Li L;Wang S;Lan H;Gong G;Zhu Y;Tse YC;Wong KM

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Two sensors, 1 with a spirolactone group and 2 with a spirolactam group containing a phenyl isothiocyanate moiety, based on rhodol, were designed and synthesized in order to obtain materials with excellent optical properties for the detection of environmentally and biologically important Hg2+ and hypochlorous acid (HClO) ions. The crystal structure of 1 revealed two moieties, a rhodamine‐like portion with a spirolactone and a fluorescein‐like portion without a spirolactone. In the absence of analyte, 1 produced an optical output with a maximum absorption and emission at 475 and 570 nm, respectively, which was attributed to the fluorescein‐like moiety without a spirolactone. In contrast, the rhodamine‐like moiety containing a spirolactone was activated by the addition of H+ or Hg2+ ions, and 1 yielded new absorption and emission peaks at 530 and 612 nm, respectively. Further functionalization with a phenyl isothiocyanate group afforded 2, a fluorescent probe for HClO. High selectivity and sensitivity towards the hypochlorite ion were anticipated, owing to the stoichiometric and irreversible formation of a thiosemicarbazide group, which led to dramatic fluorescence responses. With good functionality at physiological pH, probe 2 was successfully used to image HClO in HeLa cells.
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