@article{07c5185cf5bd4c30bad2ad0aef243735,
title = "Differential Effect of Azetidine Substitution in Firefly Luciferin Analogues",
abstract = "Replacing an N,N-dimethylamino group in a classical fluorophore with a four membered azetidine ring provides an improved luminescence quantum yield. Herein, we extended this strategy to bioluminescent firefly luciferin analogues and evaluated its general validity. For this purpose, four types of luciferin cores were employed, and a total of eight analogues were evaluated. Among these analogues, unexpectedly, only the benzothiazole core analogue benefited from an azetidine substitution and showed enhanced bioluminescence. In addition, fluorescence measurements revealed that an azetidine substitution improved the fluorescence quantum yield by 2.3-times compared to a N,N-dimethylamino group. These findings clarify the differential effects of azetidine substituents in luciferins and present one possible strategy for enhancing photon output in benzothiazole type luciferins through a synthetic approach.",
keywords = "enzyme catalysis, imaging agents, luciferins, luminescence, synthesis design",
author = "Yuma Ikeda and Mariko Orioka and Takahiro Nomoto and Yuki Hiruta and Nobuhiro Nishiyama and Daniel Citterio",
note = "Funding Information: This work was supported by a Grant‐in Aid for Scientific Research (A) (Grant No. 17H01215) to D.C., and Grant‐in‐Aid for JSPS Fellows for Young Scientist (Grant No. 19 J12615) from the Japan Society for the Promotion of Science (JSPS) to Y.I., and a Grant‐in‐Aid for Scientific Research on Innovative Areas “Singularity Biology (No. 8007)” (19H05429) from The Ministry of Education, Culture, Sports, Science, and Technology, Japan, to Y.H. We thank Dr. Kazuki Niwa, National Institute of Advanced Industrial Science and Technology (AIST) for bioluminescence quantum yield measurements. Funding Information: This work was supported by a Grant-in Aid for Scientific Research (A) (Grant No. 17H01215) to D.C., and Grant-in-Aid for JSPS Fellows for Young Scientist (Grant No. 19 J12615) from the Japan Society for the Promotion of Science (JSPS) to Y.I., and a Grant-in-Aid for Scientific Research on Innovative Areas “Singularity Biology (No. 8007)” (19H05429) from The Ministry of Education, Culture, Sports, Science, and Technology, Japan, to Y.H. We thank Dr. Kazuki Niwa, National Institute of Advanced Industrial Science and Technology (AIST) for bioluminescence quantum yield measurements. Publisher Copyright: {\textcopyright} 2021 Wiley-VCH GmbH",
year = "2021",
month = nov,
day = "3",
doi = "10.1002/cbic.202100310",
language = "English",
volume = "22",
pages = "3067--3074",
journal = "ChemBioChem",
issn = "1439-4227",
publisher = "Wiley-VCH Verlag",
number = "21",
}