Differential Effect of Azetidine Substitution in Firefly Luciferin Analogues

Yuma Ikeda, Mariko Orioka, Takahiro Nomoto, Yuki Hiruta, Nobuhiro Nishiyama, Daniel Citterio

研究成果: Article査読

抄録

Replacing an N,N-dimethylamino group in a classical fluorophore with a four membered azetidine ring provides an improved luminescence quantum yield. Herein, we extended this strategy to bioluminescent firefly luciferin analogues and evaluated its general validity. For this purpose, four types of luciferin cores were employed, and a total of eight analogues were evaluated. Among these analogues, unexpectedly, only the benzothiazole core analogue benefited from an azetidine substitution and showed enhanced bioluminescence. In addition, fluorescence measurements revealed that an azetidine substitution improved the fluorescence quantum yield by 2.3-times compared to a N,N-dimethylamino group. These findings clarify the differential effects of azetidine substituents in luciferins and present one possible strategy for enhancing photon output in benzothiazole type luciferins through a synthetic approach.

本文言語English
ページ(範囲)3067-3074
ページ数8
ジャーナルChemBioChem
22
21
DOI
出版ステータスPublished - 2021 11月 3

ASJC Scopus subject areas

  • 生化学
  • 分子医療
  • 分子生物学
  • 有機化学

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