Issue 40, 2017

Coelenterazine analogues emit red-shifted bioluminescence with NanoLuc

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

Supplementary files

Article information

Article type
Paper
Submitted
09 Aug 2017
Accepted
15 Sep 2017
First published
03 Oct 2017

Org. Biomol. Chem., 2017,15, 8559-8567

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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