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

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13 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)9330-9337
Number of pages8
JournalChemistry - A European Journal
Volume22
Issue number27
DOIs
Publication statusPublished - 2016 Jan 1

Keywords

  • biological activity
  • firefly luciferase
  • luminescence
  • structure–activity relationships
  • synthesis design

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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    Ioka, S., Saitoh, T., Iwano, S., Suzuki, K., Maki, S. A., Miyawaki, A., Imoto, M., & Nishiyama, S. (2016). Synthesis of Firefly Luciferin Analogues and Evaluation of the Luminescent Properties. Chemistry - A European Journal, 22(27), 9330-9337. https://doi.org/10.1002/chem.201600278