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Chemistry. 2016 Mar 7;22(11):3671-5. doi: 10.1002/chem.201503944. Epub 2016 Jan 19.

Design and Synthesis of an Alkynyl Luciferin Analogue for Bioluminescence Imaging.

Author information

1
Department of Chemistry, University of California, Irvine, Irvine, CA, USA.
2
Department of Chemistry, University of California, Irvine, Irvine, CA, USA. jpresche@uci.edu.
3
Department of Molecular Biology & Biochemistry, University of California, Irvine, Irvine, CA, USA. jpresche@uci.edu.
4
Department of Pharmaceutical Sciences, University of California, Irvine, Irvine, CA, USA. jpresche@uci.edu.

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.

KEYWORDS:

C−H activation; Sonogashira coupling; bioluminescence imaging; luciferase; luciferin

PMID:
26784889
PMCID:
PMC4868354
DOI:
10.1002/chem.201503944
[Indexed for MEDLINE]
Free PMC Article

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