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Synthesis of a Far-Red Photoactivatable Silicon-Containing Rhodamine for Super-Resolution Microscopy.

Jonathan B GrimmTeresa KleinBenjamin G KopekGleb ShtengelHarald F HessMarkus SauerLuke D Lavis
Published in: Angewandte Chemie (International ed. in English) (2015)
The rhodamine system is a flexible framework for building small-molecule fluorescent probes. Changing N-substitution patterns and replacing the xanthene oxygen with a dimethylsilicon moiety can shift the absorption and fluorescence emission maxima of rhodamine dyes to longer wavelengths. Acylation of the rhodamine nitrogen atoms forces the molecule to adopt a nonfluorescent lactone form, providing a convenient method to make fluorogenic compounds. Herein, we take advantage of all of these structural manipulations and describe a novel photoactivatable fluorophore based on a Si-containing analogue of Q-rhodamine. This probe is the first example of a "caged" Si-rhodamine, exhibits higher photon counts compared to established localization microscopy dyes, and is sufficiently red-shifted to allow multicolor imaging. The dye is a useful label for super-resolution imaging and constitutes a new scaffold for far-red fluorogenic molecules.
Keyphrases
  • fluorescent probe
  • living cells
  • high resolution
  • small molecule
  • single molecule
  • high throughput
  • optical coherence tomography
  • room temperature
  • quantum dots
  • mass spectrometry
  • label free
  • flow cytometry
  • solid state