Design and Synthesis of an Alkynyl Luciferin Analogue for Bioluminescence Imaging

Rachel C. Steinhardt, Jessica M. O'Neill, Colin M. Rathbun, David C. McCutcheon, Miranda A. Paley, Jennifer A. Prescher

Research output: Contribution to journalArticle

21 Scopus citations

Abstract

Herein, the synthesis and characterization of an alkyne-modified luciferin is reported. This bioluminescent probe was accessed using C-H activation methodology and was found to be stable in solution and capable of light production with firefly luciferase. The luciferin analogue was also cell permeant and emitted more redshifted light than d-luciferin, the native luciferase substrate. Based on these features, the alkynyl luciferin will be useful for a variety of imaging applications.

Original languageEnglish (US)
Pages (from-to)3671-3675
Number of pages5
JournalChemistry - A European Journal
Volume22
Issue number11
DOIs
StatePublished - Mar 7 2016

Keywords

  • C-H activation
  • Sonogashira coupling
  • bioluminescence imaging
  • luciferase
  • luciferin

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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    Steinhardt, R. C., O'Neill, J. M., Rathbun, C. M., McCutcheon, D. C., Paley, M. A., & Prescher, J. A. (2016). Design and Synthesis of an Alkynyl Luciferin Analogue for Bioluminescence Imaging. Chemistry - A European Journal, 22(11), 3671-3675. https://doi.org/10.1002/chem.201503944