1. Synthesis of Firefly Luciferin Analogues and Evaluation of the Luminescent Properties
- Author
-
Shuji Ioka, Satoshi Iwano, Shojiro Maki, Shigeru Nishiyama, Koji Suzuki, Masaya Imoto, Atsushi Miyawaki, and Tsuyoshi Saitoh
- Subjects
Stereochemistry ,Mice, Transgenic ,Firefly luciferin ,Firefly Luciferin ,010402 general chemistry ,01 natural sciences ,Catalysis ,law.invention ,Mice ,Structure-Activity Relationship ,chemistry.chemical_compound ,Luciferases, Firefly ,law ,Animals ,Moiety ,Luciferase ,Benzothiazoles ,Chemiluminescence ,Luminescent Agents ,010405 organic chemistry ,Thiazoline ,Organic Chemistry ,General Chemistry ,Luciferin ,Adenosine Monophosphate ,0104 chemical sciences ,Spectrometry, Fluorescence ,Benzothiazole ,chemistry ,Luminescent Measurements ,Light emission - 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.
- Published
- 2016
- Full Text
- View/download PDF