Issue 12, 2013

Development of cell-impermeable coelenterazine derivatives


We describe the development of the first cell-membrane impermeable coelenterazine derivative (CoelPhos). CoelPhos was constructed by the alkylation of coelenterazine with a linker containing a terminal anionic phosphonate moiety. The bioluminescence activity of CoelPhos with Gaussia luciferase (GLuc) showed a significantly higher activity in comparison with Renilla luciferase. In imaging studies with living cells, outer membrane bound GLuc was clearly imaged with CoelPhos. On the other hand no signal could be detected with intracellularly localized GLuc, demonstrating the impermeability of this novel coelenterate substrate derivative. CoelPhos has potential utility as a new bioluminogenic tool for the monitoring of dynamic fusion events at the cell–surface interface.

Graphical abstract: Development of cell-impermeable coelenterazine derivatives

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Article information

Article type
Edge Article
16 Jul 2013
03 Sep 2013
First published
03 Sep 2013
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2013,4, 4395-4400

Development of cell-impermeable coelenterazine derivatives

E. Lindberg, S. Mizukami, K. Ibata, T. Fukano, A. Miyawaki and K. Kikuchi, Chem. Sci., 2013, 4, 4395 DOI: 10.1039/C3SC51985F

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