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

Li, Ling1; Wang, Shu1; Lan, Hongxia2; Gong, Guiyi2; Zhu, Yifan1; Tse, Yu Chung2; Wong, Keith Man-Chung1

2018-02

10.1002/open.201700154

ChemistryOpen   影响因子和分区

2191-1363

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 570nm, 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 612nm, 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.

chemosensor fluorescence hypochlorous acid mercury rhodol

SCI ; EI

英语

第一 ; 通讯

Shenzhen Key Laboratory of Cell Microenvironment[ZDSYS20140509142721429]

Chemistry

Chemistry, Multidisciplinary

WOS:000426495300003

WILEY-V C H VERLAG GMBH

Web of Science

1.Southern Univ Sci & Technol, Dept Chem, 1088 Tangchang Blvd, Shenzhen 518055, Peoples R China
2.Southern Univ Sci & Technol, Dept Biol, Shenzhen Key Lab Cell Microenvironm, Guangdong Prov Key Lab Cell Microenvironm & Dis R, 1088 Tangchang Blvd, Shenzhen 518055, Peoples R China

Li, Ling,Wang, Shu,Lan, Hongxia,et al. Rhodol Derivatives as Selective Fluorescent Probes for the Detection of Hg-II Ions and the Bioimaging of Hypochlorous Acid[J]. ChemistryOpen,2018,7(2):136-143.

Li, Ling.,Wang, Shu.,Lan, Hongxia.,Gong, Guiyi.,Zhu, Yifan.,...&Wong, Keith Man-Chung.(2018).Rhodol Derivatives as Selective Fluorescent Probes for the Detection of Hg-II Ions and the Bioimaging of Hypochlorous Acid.ChemistryOpen,7(2),136-143.

Li, Ling,et al."Rhodol Derivatives as Selective Fluorescent Probes for the Detection of Hg-II Ions and the Bioimaging of Hypochlorous Acid".ChemistryOpen 7.2(2018):136-143.