Pyridinium Analogues of Green Fluorescent Protein Chromophore: Fluorogenic Dyes with Large Solvent-Dependent Stokes Shift

J Phys Chem Lett. 2018 Apr 19;9(8):1958-1963. doi: 10.1021/acs.jpclett.8b00512. Epub 2018 Apr 5.

Abstract

Novel fluorogenic dyes based on the GFP chromophore are developed. The compounds contain a pyridinium ring instead of phenolate and feature large Stokes shifts and solvent-dependent variations in the fluorescence quantum yield. Electronic structure calculations explain the trends in solvatochromic behavior in terms of the increase of the dipole moment upon excited-state relaxation in polar solvents associated with the changes in bonding pattern in the excited state. A unique combination of such optical characteristics and lipophilic properties enables using one of the new dyes for imaging the membrane structure of endoplasmic reticulum. An extremely high photostability (due to a dynamic exchange between the free and absorbed states) and selectivity make this compound a promising label for this type of cellular organelles.

MeSH terms

  • Animals
  • Fluorescent Dyes / chemistry*
  • Green Fluorescent Proteins / chemistry*
  • HeLa Cells
  • Humans
  • Mice
  • Molecular Structure
  • NIH 3T3 Cells
  • Pyridinium Compounds / chemistry*
  • Quantum Theory
  • Solvents / chemistry

Substances

  • Fluorescent Dyes
  • Pyridinium Compounds
  • Solvents
  • Green Fluorescent Proteins