New Red-Emitting Tetrazine-Phenoxazine Fluorogenic Labels for Live-Cell Intracellular Bioorthogonal Labeling Schemes

Gergely Knorr, Eszter Kozma, András Herner, Edward A. Lemke, P. Kele

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

The synthesis of a set of tetrazine-bearing fluorogenic dyes suitable for intracellular labeling of proteins in live cells is presented. The red excitability and emission properties ensure minimal autofluorescence, while through-bond energy-transfer-based fluorogenicity reduces nonspecific background fluorescence of unreacted dyes. The tetrazine motif efficiently quenches fluorescence of the phenoxazine core, which can be selectively turned on chemically upon bioorthogonal inverse-electron-demand Diels-Alder reaction with proteins modified genetically with strained trans-cyclooctenes.

Original languageEnglish
JournalChemistry - A European Journal
DOIs
Publication statusAccepted/In press - 2016

Keywords

  • Dyes/pigments
  • Energy transfer
  • Fluorescent probes
  • Imaging agents
  • Proteins

ASJC Scopus subject areas

  • Chemistry(all)

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