Molecular design strategies for near-infrared ratiometric fluorescent probes based on the unique spectral properties of aminocyanines

Chemistry. 2009 Sep 14;15(36):9191-200. doi: 10.1002/chem.200900035.

Abstract

In spite of the wide availability of various near-infrared (NIR) fluorophores as labeling reagents, there are few functional NIR fluorescent probes for which change in the absorption and/or fluorescence spectra upon specific reaction with biomolecules is seen. The widely used photoinduced electron-transfer mechanism is unsuitable for NIR fluorophores, such as tricarbocyanines, because their long excitation wavelength results in a small singlet excitation energy. We have reported the unique spectral properties of amine-substituted tricarbocyanines, which were utilized to develop two design strategies. One approach was based on control of the absorption wavelength by using the difference in electron-donating ability before and after a specific reaction with a biomolecule, and the other approach was based on control of the fluorescence intensity by modulating the Förster resonance energy-transfer efficiency through a change in the overlap integral that arises from the change in absorption under acidic conditions. These strategies were validated by obtaining tricarbocyanine-based ratiometric NIR fluorescent probes for esterase and for pH level.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbocyanines / chemistry*
  • Esterases / metabolism
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • Hydrogen-Ion Concentration
  • Molecular Structure
  • Spectroscopy, Near-Infrared

Substances

  • Carbocyanines
  • Fluorescent Dyes
  • Esterases