Development of luciferin analogues bearing an amino group and their application as BRET donors

Hideo Takakura, Kiyoshi Sasakura, Tasuku Ueno, Yasuteru Urano, Takuya Terai, Kenjiro Hanaoka, Takashi Tsuboi, Tetsuo Nagano

Research output: Contribution to journalArticlepeer-review

52 Citations (Scopus)

Abstract

We systematically synthesized bioluminogenic substrates bearing an amino group on benzothiazole, quinoline, naphthalene, and coumarin scaffolds. They emit bioluminescence in various colors: red, orange, yellow, and green. An amino-substituted cou-marylluciferin derivative, coumarylami-noluciferin (CAL), showed the shortest bioluminescence wavelength among substrates reported so far. Further, the fluorescence of CAL did not exhibit solvatochromism, which suggests that its bioluminescence is not susceptible to environmental factors. We applied CAL as an energy-donor substrate for a bioluminescence resonance energy transfer (BRET) system with click beetle red luciferase (CBRluc), a mutant of firefly luciferase, as the energy-donor enzyme and yellow fluorescent protein (YFP) as the energy-acceptor fluorophore, and obtained a clearly bimodal bioluminescence spectrum. Stable bioluminescence that is not influenced by environmental factors is highly desirable for reliable measurements in biological assays.

Original languageEnglish
Pages (from-to)2053-2061
Number of pages9
JournalChemistry - An Asian Journal
Volume5
Issue number9
DOIs
Publication statusPublished - 2010 Sep 3
Externally publishedYes

Keywords

  • BRET
  • Energy transfer
  • Luciferin analogues
  • Luminescence
  • Solvatochromism

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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