Synthesis of 7-aminocoumarin by Buchwald-Hartwig cross coupling for specific protein labeling in living cells

Chembiochem. 2011 Jan 3;12(1):65-70. doi: 10.1002/cbic.201000414.

Abstract

PRIME time: We report the synthesis of a pH-insensitive blue fluorophore, 7-aminocoumarin, by using palladium-catalyzed Buchwald–Hartwig cross coupling. 7-Aminocoumarin can be used to tag recombinant proteins on the cell surface and inside living cells through PRIME (probe incorporation mediated by enzymes), and unlike 7-hydroxycoumarin, can be visualized in acidic organelles such as endosomes.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Line
  • Cell Survival
  • Coumarins / chemical synthesis*
  • Coumarins / metabolism*
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / metabolism*
  • Humans
  • Molecular Imaging
  • Proteins / metabolism*
  • Staining and Labeling / methods*
  • Substrate Specificity

Substances

  • Coumarins
  • Fluorescent Dyes
  • Proteins
  • 7-aminocoumarin