Live-cell one- and two-photon uncaging of a far-red emitting acridinone fluorophore

J Am Chem Soc. 2010 Mar 3;132(8):2585-90. doi: 10.1021/ja9074562.


Total synthesis and photophysical properties of PENB-DDAO, a photoactivatable 1,3-dichloro-9,9-dimethyl-9H-acridin-2(7)-one (DDAO) derivative of a far-red emitting fluorophore, are described. The photoremovable group of the DDAO phenolic function comprises a donor/acceptor biphenyl platform which allows an efficient (> or = 95%) and rapid (< 15 micros time-range) release of the fluorescent signal and displays remarkable two-photon uncaging cross sections (delta(a) x Phi(u) = 3.7 GM at 740 nm). PENB-DDAO is cell permeable as demonstrated by the triggering of cytoplasmic red fluorescent signal in HeLa cells after one-photon irradiation (lambda(exc) around 360 nm) or by the generation of a red fluorescent signal in a delineated area of a single cell after two-photon photoactivation (lambda(exc) = 770 nm).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acridines / analysis*
  • Acridines / chemical synthesis
  • Acridines / metabolism
  • Cell Membrane Permeability
  • Fluorescent Dyes / analysis*
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / metabolism
  • HeLa Cells
  • Humans
  • Microscopy, Fluorescence / methods*
  • Models, Molecular
  • Photochemistry


  • Acridines
  • Fluorescent Dyes