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Synthesis of Firefly Luciferin Analogues and Evaluation of the Luminescent Properties |
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| Authors: | Shuji Ioka Dr. Tsuyoshi Saitoh Dr. Satoshi Iwano Prof. Dr. Koji Suzuki Dr. Shojiro A. Maki Prof. Dr. Atsushi Miyawaki Prof. Dr. Masaya Imoto Prof. Dr. Shigeru Nishiyama |
| Affiliation: | 1. Department of Chemistry, Faculty of Science and Technology, Keio University, Yokohama, Japan;2. Department of Biosciences and Informatics, Faculty of Science and Technology, Keio University, Yokohama, Japan;3. International Institute for Integrative Sleep Medicine (WPI-IIS), University of Tsukuba, Ibaraki, Japan;4. Department of Engineering Science, The University of Electro-Communications, Tokyo, Japan;5. Laboratory for Cell Function Dynamics, Brain Science Institute, RIKEN, Saitama, Japan;6. Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Yokohama, Japan |
| Abstract: | Five new firefly luciferin ( 1 ) analogues were synthesized and their light emission properties were examined. Modifications of the thiazoline moiety in 1 were employed to produce analogues containing acyclic amino acid side chains ( 2 – 4 ) and heterocyclic rings derived from amino acids ( 5 and 6 ) linked to the benzothiazole moiety. Although methyl esters of all of the synthetic derivatives exhibited chemiluminescence activity, only carboluciferin ( 6 ), possessing a pyrroline‐substituted benzothiazole structure, had bioluminescence (BL) activity (λmax=547 nm). Results of bioluminescence studies with AMP‐carboluciferin (AMP=adenosine monophosphate) and AMP‐firefly luciferin showed that the nature of the thiazoline mimicking moiety affected the adenylation step of the luciferin–luciferase reaction required for production of potent BL. In addition, BL of 6 in living mice differed from that of 1 in that its luminescence decay rate was slower. |
| Keywords: | biological activity firefly luciferase luminescence structure– activity relationships synthesis design |