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Issue 40, 2017
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Coelenterazine analogues emit red-shifted bioluminescence with NanoLuc

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Abstract

We report the synthesis and characterization of novel coelenterazine analogues that demonstrate a red-shift in their bioluminescent emission with NanoLuc luciferase. These coelenterazines can be tuned to shift the bioluminescent emission from blue light in the native system. In particular, direct attachment of an aryl moiety to the imidazopyrazinone core of furimazine at the C8 position provides a significant red-shift while maintaining reasonable light output. In addition, modification of the C6 aryl moiety provided additive red-shifts, and by combining the most promising modifications we report a coelenterazine with a maximum emission near 600 nm with NanoLuc. Finally, we show that this new bioluminescent system is capable of efficient BRET to far-red fluorophores. We anticipate these new principles of NanoLuc substrate design will impact applications that depend on shifting the colour of emission to the red, most notably in vivo bioluminescent imaging.

Graphical abstract: Coelenterazine analogues emit red-shifted bioluminescence with NanoLuc

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Publication details

The article was received on 09 Aug 2017, accepted on 15 Sep 2017 and first published on 03 Oct 2017


Article type: Paper
DOI: 10.1039/C7OB01985H
Citation: Org. Biomol. Chem., 2017,15, 8559-8567
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    Coelenterazine analogues emit red-shifted bioluminescence with NanoLuc

    A. Shakhmin, M. P. Hall, T. Machleidt, J. R. Walker, K. V. Wood and T. A. Kirkland, Org. Biomol. Chem., 2017, 15, 8559
    DOI: 10.1039/C7OB01985H

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