Brominated Luciferins Are Versatile Bioluminescent Probes

Rachel Steinhardt, Colin M. Rathbun, Brandon T. Krull, Jason M. Yu, Yuhang Yang, Brian D. Nguyen, Jake Kwon, David C. McCutcheon, Krysten A. Jones, Filipp Furche, Jennifer A. Prescher

Research output: Contribution to journalArticle

18 Scopus citations

Abstract

We report a set of brominated luciferins for bioluminescence imaging. These regioisomeric scaffolds were accessed by using a common synthetic route. All analogues produced light with firefly luciferase, although varying levels of emission were observed. Differences in photon output were analyzed by computation and photophysical measurements. The brightest brominated luciferin was further evaluated in cell and animal models. At low doses, the analogue outperformed the native substrate in cells. The remaining luciferins, although weak emitters with firefly luciferase, were inherently capable of light production and thus potential substrates for orthogonal mutant enzymes.

Original languageEnglish (US)
Pages (from-to)96-100
Number of pages5
JournalChemBioChem
Volume18
Issue number1
DOIs
StatePublished - Jan 3 2017
Externally publishedYes

Keywords

  • Appel's salt
  • bioluminescence
  • imaging
  • luciferase
  • luciferin

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Organic Chemistry

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  • Cite this

    Steinhardt, R., Rathbun, C. M., Krull, B. T., Yu, J. M., Yang, Y., Nguyen, B. D., Kwon, J., McCutcheon, D. C., Jones, K. A., Furche, F., & Prescher, J. A. (2017). Brominated Luciferins Are Versatile Bioluminescent Probes. ChemBioChem, 18(1), 96-100. https://doi.org/10.1002/cbic.201600564