Expedient synthesis of electronically modified luciferins for bioluminescence imaging

David C. McCutcheon, Miranda A. Paley, Rachel C. Steinhardt, Jennifer A. Prescher

Research output: Contribution to journalArticle

69 Scopus citations

Abstract

Bioluminescence imaging with luciferase enzymes requires access to light-emitting, small-molecule luciferins. Here, we describe a rapid method to synthesize d-luciferin, the substrate for firefly luciferase (Fluc), along with a novel set of electronically modified analogues. Our procedure utilizes a relatively rare, but synthetically useful dithiazolium reagent to generate heteroaromatic scaffolds in a divergent fashion. Two of the luciferin analogues produced with this approach emit light with Fluc in vitro and in live cells. Collectively, our work increases the number of substrates that can be used for bioluminescence imaging and provides a general strategy for synthesizing new collections of luciferins.

Original languageEnglish (US)
Pages (from-to)7604-7607
Number of pages4
JournalJournal of the American Chemical Society
Volume134
Issue number18
DOIs
StatePublished - May 9 2012

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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