Quantum yield improvement of red-light-emitting firefly luciferin analogues for in vivo bioluminescence imaging

Masahiro Kiyama, Satoshi Iwano, Satoshi Otsuka, Shijia W. Lu, Rika Obata, Atsushi Miyawaki, Takashi Hirano, Shojiro A. Maki

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

The dimethylamino group of AkaLumine ((4S)-2-[(1E,3E)-4-[4-(dimethylamino)phenyl]-1,3-butadien-1-yl]-4,5-dihydro-4-thiazolecarboxylic acid), a red-light-emitting firefly luciferin analogue, was replaced by cyclic amino groups (1-pyrrolidinyl, 1-piperidino, 1-azepanyl, and 4-morpholino) to give AkaLumine analogues exhibiting desirable bioluminescence with emission maxima in the red region (656–667 nm). In particular, a bioluminescence reaction of 1-pyrrolidinyl analogue with a recombinant Photinus pyralis luciferase showed a higher quantum yield than that with AkaLumine, giving an improved bioluminescence intensity. The 1-pyrrolidinyl analogue also showed the strongest luminescence in whole-body luciferase-expressing mice among the analogues, indicating that a quantum yield improvement of a luciferin analogue is effective to increase bioluminescence imaging intensity.

Original languageEnglish
Pages (from-to)652-660
Number of pages9
JournalTetrahedron
Volume74
Issue number6
DOIs
Publication statusPublished - 2018 Feb 8

Keywords

  • Bioluminescence imaging
  • Enzyme kinetics
  • Firefly luciferin
  • Quantum yield
  • Red-light-emitting

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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  • Cite this

    Kiyama, M., Iwano, S., Otsuka, S., Lu, S. W., Obata, R., Miyawaki, A., Hirano, T., & Maki, S. A. (2018). Quantum yield improvement of red-light-emitting firefly luciferin analogues for in vivo bioluminescence imaging. Tetrahedron, 74(6), 652-660. https://doi.org/10.1016/j.tet.2017.11.051