TY - JOUR
T1 - Quantum yield improvement of red-light-emitting firefly luciferin analogues for in vivo bioluminescence imaging
AU - Kiyama, Masahiro
AU - Iwano, Satoshi
AU - Otsuka, Satoshi
AU - Lu, Shijia W.
AU - Obata, Rika
AU - Miyawaki, Atsushi
AU - Hirano, Takashi
AU - Maki, Shojiro A.
N1 - Funding Information:
This work was supported by Grant-in-Aid for Scientific Research on Innovative Areas “Resonance Bio” (No. 15H05948 ) to S. A. M. from the Ministry of Education, Culture, Sports, Science and Technology , and Adaptable & Seamless Technology Transfer Program through Target-driven R&D (A-Step) (No. AS2614119N ) to S. A. M. from the Japan Science and Technology Agency . We thank the Information Technology Center of UEC for technical assistance in computing DFT calculations.
Publisher Copyright:
© 2017
PY - 2018/2/8
Y1 - 2018/2/8
N2 - 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.
AB - 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.
KW - Bioluminescence imaging
KW - Enzyme kinetics
KW - Firefly luciferin
KW - Quantum yield
KW - Red-light-emitting
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U2 - 10.1016/j.tet.2017.11.051
DO - 10.1016/j.tet.2017.11.051
M3 - Article
AN - SCOPUS:85039749111
VL - 74
SP - 652
EP - 660
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 6
ER -