Determination of intracellular pH using sensitive, clickable fluorescent probes

Bioorg Med Chem Lett. 2012 Apr 1;22(7):2440-3. doi: 10.1016/j.bmcl.2012.02.021. Epub 2012 Feb 16.

Abstract

We synthesized and evaluated a series of acidic fluorescent pH probes exhibiting robust pH dependence, high sensitivity and photostability, and excellent cell membrane permeability. Titration analyses indicated that probe 3 could increase its fluorescence intensity 800-fold between pH 8.0 and 4.1. Additionally, its pK(a) value is optimal for intracellular probing of acidic organelles. Fluorescent imaging of HepG2 and Hela cells further revealed that probe 3 demonstrates outstanding capacity for monitoring of intracellular [H(+)] levels. The easily accessible terminal alkyne/azido function groups of these probes offer the possibility of rapidly constructing sensor molecule libraries using 'click' chemistry.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Acids
  • Biosensing Techniques*
  • Cell Membrane Permeability
  • Cytoplasm / chemistry
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / chemistry
  • HeLa Cells
  • Hep G2 Cells
  • Humans
  • Hydrogen-Ion Concentration
  • Lactams / chemical synthesis*
  • Lactams / chemistry
  • Organelles / chemistry
  • Protons
  • Rhodamines / chemical synthesis*
  • Rhodamines / chemistry
  • Spectrometry, Fluorescence

Substances

  • Acids
  • Fluorescent Dyes
  • Lactams
  • Protons
  • Rhodamines