Development of cell-impermeable coelenterazine derivatives

Eric Lindberg, Shin Mizukami, Keiji Ibata, Takashi Fukano, Atsushi Miyawaki, Kazuya Kikuchi

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

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. This journal is

Original languageEnglish
Pages (from-to)4395-4400
Number of pages6
JournalChemical Science
Volume4
Issue number12
DOIs
Publication statusPublished - 2013 Dec

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Luciferases
Cell membranes
Derivatives
Renilla Luciferases
Bioluminescence
Organophosphonates
Alkylation
Fusion reactions
Imaging techniques
Monitoring
Substrates
coelenterazine

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Lindberg, E., Mizukami, S., Ibata, K., Fukano, T., Miyawaki, A., & Kikuchi, K. (2013). Development of cell-impermeable coelenterazine derivatives. Chemical Science, 4(12), 4395-4400. https://doi.org/10.1039/c3sc51985f

Development of cell-impermeable coelenterazine derivatives. / Lindberg, Eric; Mizukami, Shin; Ibata, Keiji; Fukano, Takashi; Miyawaki, Atsushi; Kikuchi, Kazuya.

In: Chemical Science, Vol. 4, No. 12, 12.2013, p. 4395-4400.

Research output: Contribution to journalArticle

Lindberg, E, Mizukami, S, Ibata, K, Fukano, T, Miyawaki, A & Kikuchi, K 2013, 'Development of cell-impermeable coelenterazine derivatives', Chemical Science, vol. 4, no. 12, pp. 4395-4400. https://doi.org/10.1039/c3sc51985f
Lindberg E, Mizukami S, Ibata K, Fukano T, Miyawaki A, Kikuchi K. Development of cell-impermeable coelenterazine derivatives. Chemical Science. 2013 Dec;4(12):4395-4400. https://doi.org/10.1039/c3sc51985f
Lindberg, Eric ; Mizukami, Shin ; Ibata, Keiji ; Fukano, Takashi ; Miyawaki, Atsushi ; Kikuchi, Kazuya. / Development of cell-impermeable coelenterazine derivatives. In: Chemical Science. 2013 ; Vol. 4, No. 12. pp. 4395-4400.
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