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Synthesis of Firefly Luciferin Analogues and Evaluation of the Luminescent Properties
Author(s) -
Ioka Shuji,
Saitoh Tsuyoshi,
Iwano Satoshi,
Suzuki Koji,
Maki Shojiro A.,
Miyawaki Atsushi,
Imoto Masaya,
Nishiyama Shigeru
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201600278
Subject(s) - luciferin , benzothiazole , moiety , bioluminescence , luciferase , chemistry , photoprotein , chemiluminescence , stereochemistry , combinatorial chemistry , biochemistry , organic chemistry , transfection , gene
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 ( λ max =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.