Details

Autor(en) / Beteiligte

• Li, Ling
• Wang, Shu
• Lan, Hongxia
• Gong, Guiyi
• Zhu, Yifan
• Tse, Yu Chung
• Wong, Keith Man‐Chung

Titel

Rhodol Derivatives as Selective Fluorescent Probes for the Detection of HgII Ions and the Bioimaging of Hypochlorous Acid

Ist Teil von

• ChemistryOpen (Weinheim), 2018-02, Vol.7 (2), p.136-143

Ort / Verlag

Weinheim: John Wiley & Sons, Inc

Erscheinungsjahr

2018

Link zum Volltext

Quelle

Wiley Online Library All Journals

Beschreibungen/Notizen

• 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. Get the picture: A series of rhodol derivatives with extended π conjugation are reported to give selective sensing properties. Those functionalized with a phenyl isothiocyanate group can serve as a fluorescent probe for bioimaging of endogenous HClO within HeLa cells.