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Development of Luciferin Analogues Bearing an Amino Group and Their Application as BRET Donors

  1. Hideo Takakura1,2,
  2. Kiyoshi Sasakura1,2,
  3. Tasuku Ueno Dr.1,2,
  4. Yasuteru Urano Prof. Dr.3,
  5. Takuya Terai1,2,
  6. Kenjiro Hanaoka Dr.1,2,
  7. Takashi Tsuboi Dr.4,
  8. Tetsuo Nagano Prof. Dr.1,2

Article first published online: 26 JUL 2010

DOI: 10.1002/asia.201000219

Issue

Chemistry – An Asian Journal

Chemistry – An Asian Journal

Volume 5, Issue 9, pages 2053–2061, September 3, 2010

Additional Information

How to Cite

Takakura, H., Sasakura, K., Ueno, T., Urano, Y., Terai, T., Hanaoka, K., Tsuboi, T. and Nagano, T. (2010), Development of Luciferin Analogues Bearing an Amino Group and Their Application as BRET Donors. Chem. Asian J., 5: 2053–2061. doi: 10.1002/asia.201000219

Author Information

  1. 1

    Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81) 3-5841-4855

  2. 2

    CREST Japan Science and Technology Agency, Honcho, Kawaguchi, Saitama 332-0012 (Japan)

  3. 3

    Graduate School of Medicine, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)

  4. 4

    Graduate School of Arts and Sciences, The University of Tokyo, 3-8-1 Komaba, Meguro-ku, Tokyo 153-8902 (Japan)

Publication History

  1. Issue published online: 30 AUG 2010
  2. Article first published online: 26 JUL 2010
  3. Manuscript Received: 23 MAR 2010

Funded by

  • Ministry of Education, Culture, Sports, Science and Technology of the Japan. Grant Numbers: 19205021, 20117003, 21750135, 20689001, 19890047, 21659024
  • Industrial Technology Development Organization

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Keywords:

  • energy transfer;
  • BRET;
  • luciferin analogues;
  • luminescence;
  • solvatochromism

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 coumarylluciferin derivative, coumarylaminoluciferin (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.

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