Synthesis of Firefly Luciferin Analogues and Evaluation of the Luminescent Properties

Shuji Ioka, Tsuyoshi Saitoh, Satoshi Iwano, Koji Suzuki, Shojiro A. Maki, Atsushi Miyawaki, Masaya Imoto, Shigeru Nishiyama

研究成果: Article査読

15 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)9330-9337
ページ数8
ジャーナルChemistry - A European Journal
22
27
DOI
出版ステータスPublished - 2016 6 27

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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