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 journal › Article

5 Citations (Scopus)

Abstract

The dimethylamino group of AkaLumine ((4. S)-2-[(1. E,3. E)-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
JournalTetrahedron
DOIs
Publication statusAccepted/In press - 2017 Jan 1

Fingerprint

lissamine rhodamine B
Firefly Luciferin
Bioluminescence
Morpholinos
Quantum yield
Luminescence
Luciferases
Imaging techniques
Light
Acids
Photinus luciferase

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Kiyama, M., Iwano, S., Otsuka, S., Lu, S. W., Obata, R., Miyawaki, A., ... Maki, S. A. (Accepted/In press). Quantum yield improvement of red-light-emitting firefly luciferin analogues for in vivo bioluminescence imaging. Tetrahedron. https://doi.org/10.1016/j.tet.2017.11.051

Quantum yield improvement of red-light-emitting firefly luciferin analogues for in vivo bioluminescence imaging. / Kiyama, Masahiro; Iwano, Satoshi; Otsuka, Satoshi; Lu, Shijia W.; Obata, Rika; Miyawaki, Atsushi; Hirano, Takashi; Maki, Shojiro A.

In: Tetrahedron, 01.01.2017.

Research output: Contribution to journal › Article

Kiyama, M, Iwano, S, Otsuka, S, Lu, SW, Obata, R, Miyawaki, A, Hirano, T & Maki, SA 2017, 'Quantum yield improvement of red-light-emitting firefly luciferin analogues for in vivo bioluminescence imaging', Tetrahedron. https://doi.org/10.1016/j.tet.2017.11.051
Kiyama M, Iwano S, Otsuka S, Lu SW, Obata R, Miyawaki A et al. Quantum yield improvement of red-light-emitting firefly luciferin analogues for in vivo bioluminescence imaging. Tetrahedron. 2017 Jan 1. https://doi.org/10.1016/j.tet.2017.11.051
Kiyama, Masahiro ; Iwano, Satoshi ; Otsuka, Satoshi ; Lu, Shijia W. ; Obata, Rika ; Miyawaki, Atsushi ; Hirano, Takashi ; Maki, Shojiro A. / Quantum yield improvement of red-light-emitting firefly luciferin analogues for in vivo bioluminescence imaging. In: Tetrahedron. 2017.
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abstract = "The dimethylamino group of AkaLumine ((4. S)-2-[(1. E,3. E)-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.",
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AU - Otsuka, Satoshi

AU - Lu, Shijia W.

AU - Obata, Rika

AU - Miyawaki, Atsushi

AU - Hirano, Takashi

AU - Maki, Shojiro A.

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N2 - The dimethylamino group of AkaLumine ((4. S)-2-[(1. E,3. E)-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.

AB - The dimethylamino group of AkaLumine ((4. S)-2-[(1. E,3. E)-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.

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KW - Quantum yield

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