A PEGylated fluorescent turn-on sensor for detecting fluoride ions in totally aqueous media and its imaging in live cells

Chemistry. 2013 Jan 14;19(3):936-42. doi: 10.1002/chem.201202732. Epub 2012 Nov 29.

Abstract

Owing to the considerable significance of fluoride anions for health and environmental issues, it is of great importance to develop methods that can rapidly, sensitively and selectively detect the fluoride anion in aqueous media and biological samples. Herein, we demonstrate a robust fluorescent turn-on sensor for detecting the fluoride ion in a totally aqueous solution. In this study, a biocompatible hydrophilic polymer poly(ethylene glycol) (PEG) is incorporated into the sensing system to ensure water solubility and to enhance biocompatibility. tert-Butyldiphenylsilyl (TBDPS) groups were then covalently introduced onto the fluorescein moiety, which effectively quenched the fluorescence of the sensor. Upon addition of fluoride ion, the selective fluoride-mediated cleavage of the Si-O bond leads to the recovery of the fluorescein moiety, resulting in a dramatic increase in fluorescence intensity under visible light excitation. The sensor is responsive and highly selective for the fluoride anion over other common anions; it also exhibits a very low detection limit of 19 ppb. In addition, this sensor is operative in some real samples such as running water, urine, and serum and can accurately detect fluoride ions in these samples. The cytotoxicity of the sensor was determined to be Grade I toxicity according to United States Pharmacopoeia and ISO 10993-5, suggesting the very low cytotoxicity of the sensor. Moreover, it was found that the senor could be readily internalized by both HeLa and L929 cells and the sensor could be utilized to track fluoride level changes inside the cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Line, Tumor
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • Fluorescent Dyes / pharmacokinetics
  • Fluorides / analysis*
  • HeLa Cells
  • Humans
  • Ions / analysis
  • Mice
  • Molecular Structure
  • Polyethylene Glycols / chemical synthesis
  • Polyethylene Glycols / chemistry*
  • Polyethylene Glycols / pharmacokinetics
  • Water / chemistry

Substances

  • Fluorescent Dyes
  • Ions
  • Water
  • Polyethylene Glycols
  • Fluorides