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Modular Synthetic Approach to Silicon-Rhodamine Homologues and Analogues via Bis-aryllanthanum Reagents.

Alexey N Butkevich
Published in: Organic letters (2021)
A modular synthetic approach toward diverse analogues of the far-red fluorophore silicon-rhodamine (SiR), based on a regioselective double nucleophilic addition of aryllanthanum reagents to esters, anhydrides, and lactones, is proposed. The reaction has improved functional group tolerance and represents a unified strategy toward cell-permeant, spontaneously blinking, and photoactivatable SiR fluorescent labels. In tandem with Pd-catalyzed hydroxy- or aminocarbonylation, it serves a streamlined synthetic pathway to a series of validated live-cell-compatible fluorescent dyes.
Keyphrases
  • fluorescent probe
  • living cells
  • quantum dots
  • molecular docking
  • single cell
  • cell therapy
  • label free
  • room temperature
  • stem cells
  • ionic liquid
  • structure activity relationship
  • crystal structure