A novel acidic pH fluorescent probe based on a benzothiazole derivative

Spectrochim Acta A Mol Biomol Spectrosc. 2017 Apr 15:177:6-13. doi: 10.1016/j.saa.2017.01.024. Epub 2017 Jan 12.

Abstract

A novel acidic pH fluorescent probe 1 based on a benzothiazole derivative has been designed, synthesized and developed. The linear response range covers the acidic pH range from 3.44 to 6.46, which is valuable for pH researches in acidic environment. The evaluated pKa value of the probe 1 is 4.23. The fluorescence enhancement of the studied probe 1 with an increase in hydrogen ions concentration is based on the hindering of enhanced photo-induced electron transfer (PET) process. Moreover, the pH sensor possesses a highly selective response to H+ in the presence of metal ions, anions and other bioactive small molecules which would be interfere with its fluorescent pH response. Furthermore, the probe 1 responds to acidic pH with short response time that was less than 1min. The probe 1 has been successfully applied to confocal fluorescence imaging in live HeLa cells and can selectively stain lysosomes. All of such good properties prove it can be used to monitoring pH fluctuations in acidic environment with high sensitivity, pH dependence and short response time.

Keywords: Acidic pH fluorescent probe; Benzothiazole derivative; Cell imaging; Enhanced PET process.

MeSH terms

  • Benzothiazoles / chemical synthesis
  • Benzothiazoles / chemistry*
  • Carbon-13 Magnetic Resonance Spectroscopy
  • Cell Death
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • HeLa Cells
  • Humans
  • Hydrogen-Ion Concentration
  • Osmolar Concentration
  • Proton Magnetic Resonance Spectroscopy
  • Spectrometry, Fluorescence
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrophotometry, Ultraviolet

Substances

  • Benzothiazoles
  • Fluorescent Dyes
  • benzothiazole