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- Title
Synthesis of Firefly Luciferin Analogues and Evaluation of the Luminescent Properties.
- Authors
Ioka, Shuji; Saitoh, Tsuyoshi; Iwano, Satoshi; Suzuki, Koji; Maki, Shojiro A.; Miyawaki, Atsushi; Imoto, Masaya; Nishiyama, Shigeru
- 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.
- Subjects
AMINO acids; BIOLUMINESCENCE; ADENOSINE monophosphate; THIAZOLINES; ESTERS
- Publication
Chemistry - A European Journal, 2016, Vol 22, Issue 27, p9330
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201600278