Skip to main content
SpringerLink
Log in

Lighting up bioluminescence with coelenterazine: strategies and applications

  • Perspective
  • Published:
Photochemical & Photobiological Sciences Aims and scope Submit manuscript

Abstract

Bioluminescence-based techniques, such as bioluminescence imaging, BRET and dual-luciferase reporter assay systems, have been widely used to examine a myriad of biological processes. Coelenterazine (CTZ), a luciferin or light-producing compound found in bioluminescent organisms, has sparked great curiosity and interest in searching for analogues with improved photochemical properties. This review summarizes the current development of coelenterazine analogues, their bioluminescence properties, and the rational design of caged coelenterazine towards biotargets, as well as their applications in bioassays. It should be emphasized that the design of caged luciferins can provide valuable insight into detailed molecular processes in organisms and will be a trend in the development of bioluminescent molecules.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Notes and references

  1. S. H. Haddock, M. A. Moline, J. F. Case, Annu. Rev. Mar. Sci., 2010, 2, 443–493.

    Article  Google Scholar 

  2. J. W. Hastings, K. H. Nealson, Annu. Rev. Microbiol., 1977, 31, 549–595.

    Article  CAS  PubMed  Google Scholar 

  3. S. M. Marques, J. C. Esteves da Silva, IUBMB Life, 2009, 61, 6–17.

    Article  CAS  PubMed  Google Scholar 

  4. J. Li, L. Chen, L. Du, M. Li, Chem. Soc. Rev., 2013, 42, 662–676.

    Article  CAS  PubMed  Google Scholar 

  5. E. A. Meighen, FASEB J., 1993, 7, 1016–1022.

    Article  CAS  PubMed  Google Scholar 

  6. O. Shimomura, Bioluminescence: Chemical Principles and Methods, World Scientific Publishing Co. Pte. Ltd, 2006.

    Book  Google Scholar 

  7. M. J. Cormier, J. Biol. Chem., 1962, 237, 2032–2037.

    Article  CAS  PubMed  Google Scholar 

  8. M. J. Cormier, Light and life, Johns Hopkins Press, Baltimore, 1961.

    Google Scholar 

  9. O. Shimomura, F. H. Johnson, Y. Saiga, J. Cell. Comp. Physiol., 1962, 59, 223–239.

    Article  CAS  PubMed  Google Scholar 

  10. O. Shimomura, F. H. Johnson, Y. Saiga, J. Cell. Comp. Physiol., 1963, 62, 1–8.

    Article  CAS  PubMed  Google Scholar 

  11. O. Shimomura, F. H. Johnson, Biochemistry, 1972, 11, 1602–1608.

    Article  CAS  PubMed  Google Scholar 

  12. O. Shimomura, F. H. Johnson, Tetrahedron Lett., 1973, 14, 2963–2966.

    Article  Google Scholar 

  13. O. Shimomura, F. H. Johnson, Proc. Natl. Acad. Sci. U. S. A., 1975, 72, 1546–1549.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. O. Shimomura, F. H. Johnson, H. Morise, Biochemistry, 1974, 13, 3278–3286.

    Article  CAS  PubMed  Google Scholar 

  15. S. Inoue, S. Sugiura, H. Kakoi, K. Hasizume, T. Goto, H. Iio, Chem. Lett., 1975, 4, 141–144.

    Article  Google Scholar 

  16. S. Inoue, H. Kakoi, M. Murata, T. Goto, O. Shimomura, Tetrahedron Lett., 1977, 18, 2685–2688.

    Article  Google Scholar 

  17. K. Hori, H. Charbonneau, R. C. Hart, M. J. Cormier, Proc. Natl. Acad. Sci. U. S. A., 1977, 74, 4285–4287.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  18. M. Mosrin, T. Bresser, P. Knochel, Org. Lett., 2009, 11, 3406–3409.

    Article  CAS  PubMed  Google Scholar 

  19. P. Dunlap, Adv. Biochem. Eng./Biotechnol., 2014, 144, 37–64.

    CAS  Google Scholar 

  20. O. Shimomura, K. Teranishi, Luminescence, 2000, 15, 51–58.

    Article  CAS  PubMed  Google Scholar 

  21. K. Teranishi, Bioorg. Chem., 2007, 35, 82–111.

    Article  CAS  PubMed  Google Scholar 

  22. K. Teranishi, M. Hisamatsu, T. Yamada, Luminescence, 1999, 14, 297–302.

    Article  CAS  PubMed  Google Scholar 

  23. T. Hirano, Y. Takahashi, H. Kondo, S. Maki, S. Kojima, H. Ikeda, H. Niwa, Photochem. Photobiol. Sci., 2008, 7, 197–207.

    Article  CAS  PubMed  Google Scholar 

  24. R. Saito, T. Hirano, H. Niwa, M. Ohashi, Chem. Lett., 1998, 27, 95–96.

    Article  Google Scholar 

  25. H. Nakamura, C. Wu, D. Takeuchi, A. Murai, Tetrahedron Lett., 1998, 39, 301–304.

    Article  CAS  Google Scholar 

  26. K. Teranishi, O. Shimomura, Anal. Biochem., 1997, 249, 37–43.

    Article  CAS  PubMed  Google Scholar 

  27. O. Shimomura, C. Wu, A. Murai, H. Nakamura, Anal. Biochem., 1998, 258, 230–235.

    Article  CAS  PubMed  Google Scholar 

  28. M. Adamczyk, S. R. Akireddy, D. D. Johnson, P. G. Mattingly, Y. Pan, R. E. Reddy, Tetrahedron, 2003, 59, 8129–8142.

    Article  CAS  Google Scholar 

  29. R. Saito, T. Hirano, S. Maki, H. Niwa, M. Ohashi, Bull. Chem. Soc. Jpn., 2011, 84, 90–99.

    Article  CAS  Google Scholar 

  30. K. Teranishi, T. Goto, Chem. Lett., 1989, 18, 1423–1426.

    Article  Google Scholar 

  31. K. Teranishi, T. Goto, Bull. Chem. Soc. Jpn., 1990, 63, 3132–3140.

    Article  CAS  Google Scholar 

  32. S. Inouye, K. Watanabe, H. Nakamura, O. Shimomura, FEBS Lett., 2000, 481, 19–25.

    Article  CAS  PubMed  Google Scholar 

  33. O. Shimomura, T. Masugi, F. H. Johnson, Y. Haneda, Biochemistry, 1978, 17, 994–998.

    Article  CAS  PubMed  Google Scholar 

  34. M. P. Hall, J. Unch, B. F. Binkowski, M. P. Valley, B. L. Butler, M. G. Wood, P. Otto, K. Zimmerman, G. Vidugiris, T. Machleidt, M. B. Robers, H. A. Benink, C. T. Eggers, M. R. Slater, P. L. Meisenheimer, D. H. Klaubert, F. Fan, L. P. Encell, K. V. Wood, ACS Chem. Biol., 2012, 7, 1848–1857.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  35. S. Inouye, J.-i. Sato, Y. Sahara-Miura, S. Yoshida, H. Kurakata, T. Hosoya, Biochem. Biophys. Res. Commun., 2013, 437, 23–28.

    Article  CAS  PubMed  Google Scholar 

  36. Y. Tomabechi, T. Hosoya, H. Ehara, S.-i. Sekine, M. Shirouzu, S. Inouye, Biochem. Biophys. Res. Commun., 2016, 470, 88–93.

    Article  CAS  PubMed  Google Scholar 

  37. J. C. Matthews, K. Hori, M. J. Cormier, Biochemistry, 1977, 16, 85–91.

    Article  CAS  PubMed  Google Scholar 

  38. R. C. Hart, J. C. Matthews, K. Hori, M. J. Cormier, Biochemistry, 1979, 18, 2204–2210.

    Article  CAS  PubMed  Google Scholar 

  39. S. Inouye, O. Shimomura, Biochem. Biophys. Res. Commun., 1997, 233, 349–353.

    Article  CAS  PubMed  Google Scholar 

  40. O. Shimomura, Biochem. J., 1995, 306Pt 2, 537–543.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  41. O. Shimomura, Biochem. J., 1986, 234, 271–277.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  42. H. Charbonneau, K. A. Walsh, R. O. McCann, F. G. Prendergast, M. J. Cormier, T. C. Vanaman, Biochemistry, 1985, 24, 6762–6771.

    Article  CAS  PubMed  Google Scholar 

  43. H. Charbonneau, K. A. Walsh, R. O. McCann, F. G. Prendergast, M. J. Cormier, T. C. Vanaman, Biochemistry, 1985, 24, 6762–6771.

    Article  CAS  PubMed  Google Scholar 

  44. M. Verhaegent, T. K. Christopoulos, Anal. Chem., 2002, 74, 4378–4385.

    Article  PubMed  CAS  Google Scholar 

  45. S. Inouye, Y. Sahara, Biochem. Biophys. Res. Commun., 2008, 365, 96–101.

    Article  CAS  PubMed  Google Scholar 

  46. B. J. Bryan, US Pat., US6232107B1, 2001.

    Google Scholar 

  47. T. Suzuki, S. Usuda, H. Ichinose, S. Inouye, FEBS Lett., 2007, 581, 4551–4556.

    Article  CAS  PubMed  Google Scholar 

  48. B. A. Tannous, Nat. Protoc., 2009, 4, 582–591.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  49. M. Liu, C. Blinn, S. M. McLeod, J. W. Wiseman, J. V. Newman, S. L. Fisher, G. K. Walkup, PLoS One, 2014, 9, e90382.

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  50. K. Hori, J. E. Wampler, J. C. Matthews, M. J. Cormier, Biochemistry, 1973, 12, 4463–4468.

    Article  CAS  PubMed  Google Scholar 

  51. K. Hori, J. M. Anderson, W. W. Ward, M. J. Cormier, Biochemistry, 1975, 14, 2371–2376.

    Article  CAS  PubMed  Google Scholar 

  52. O. Shimomura, B. Musicki, Y. Kishi, Biochem. J., 1988, 251, 405–410.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  53. O. Shimomura, B. Musicki, Y. Kishi, Biochem. J., 1989, 261, 913–920.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  54. O. Shimomura, S. Inouye, B. Musicki, Y. Kishi, Biochem. J., 1990, 270, 309–312.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  55. N. P. Malikova, A. J. Borgdorff, E. S. Vysotski, Photochem. Photobiol. Sci., 2015, 14, 2213–2224.

    Article  CAS  PubMed  Google Scholar 

  56. C. F. Qi, Y. Gomi, M. Ohashi, Y. Ohmiya, F. I. Tsuji, J. Chem. Soc., Chem. Commun., 1991, 1307–1309 10.1039/C39910001307

    Google Scholar 

  57. C. F. Qi, Y. Gomi, T. Hirano, M. Ohashi, Y. Ohmiya, F. I. Tsuji, J. Chem. Soc., Perkin Trans. 1, 1992, 1607–1611 10.1039/P19920001607

    Google Scholar 

  58. F.-Q. Chen, T. Hirano, Y. Hashizume, Y. Ohmiya, M. Ohashi, J. Chem. Soc., Chem. Commun., 1994, 2405–2406 10.1039/C39940002405

    Google Scholar 

  59. F. Q. Chen, J. L. Zheng, T. Hirano, H. Niwa, Y. Ohmiya, M. Ohashi, J. Chem. Soc., Perkin Trans. 1, 1995, 2129. 10.1039/p19950002129

    Google Scholar 

  60. J. L. Zheng, F. Q. Chen, T. Hirano, Y. Ohmiya, S. Maki, H. Niwa, M. Ohashi, Bull. Chem. Soc. Jpn., 2000, 73, 465–469.

    Article  CAS  Google Scholar 

  61. T. Hirano, R. Negishi, M. Yamaguchi, F. Q. Chen, Y. Ohmiya, F. I. Tsuji, M. Ohashi, J. Chem. Soc., Chem. Commun., 1995, 1335–1336 10.1039/C39950001335

    Google Scholar 

  62. T. Hirano, R. Negishi, M. Yamaguchi, F. Q. Chen, Y. Ohmiya, F. I. Tsuji, M. Ohashi, Tetrahedron, 1997, 53, 12903–12916.

    Article  CAS  Google Scholar 

  63. S. Inouye, Y. Miura, S. Yoshida and T. Hosoya, JP Pat., US2012232272A1, 2012.

    Google Scholar 

  64. C. Wu, H. Nakamura, A. Murai, O. Shimomura, Tetrahedron Lett., 2001, 42, 2997–3000.

    Article  CAS  Google Scholar 

  65. S. Inouye, R. Iimori, Y. Sahara, S. Hisada, T. Hosoya, Anal. Biochem., 2010, 407, 247–252.

    Article  CAS  PubMed  Google Scholar 

  66. D. H. Klaubert, P. Meisenheimer and J. Unch, US Pat., US20120117667A1, 2012

  67. B. Binkowski, L. P. Encell, M. Hall, M. B. Robers, M. R. Slater, K. V. Wood and M. G. Wood, US Pat., US8669103B2, 2014.

    Google Scholar 

  68. S. Inouye, J. Sato and Y. Miura, JP Pat., US2014302539A1, 2014.

    Google Scholar 

  69. S. Inouye, Y. Sahara-Miura, J. Sato, R. Iimori, S. Yoshida, T. Hosoya, Protein Expression Purif., 2013, 88, 150–156.

    Article  CAS  Google Scholar 

  70. S. Inouye, Y. Sahara and T. Hosoya, JP Pat., US 20110244481 A1, 2011.

    Google Scholar 

  71. G. Giuliani, P. Molinari, G. Ferretti, A. Cappelli, M. Anzini, S. Vomero, T. Costa, Tetrahedron Lett., 2012, 53, 5114–5118.

    Article  CAS  Google Scholar 

  72. B. Bryan, H. Schmidt and M. Cull, US Pat., WO2014036482A2, 2014.

    Google Scholar 

  73. R. Nishihara, H. Suzuki, E. Hoshino, S. Suganuma, M. Sato, T. Saitoh, S. Nishiyama, N. Iwasawa, D. Citterio, K. Suzuki, Chem. Commun., 2015, 51, 391–394.

    Article  CAS  Google Scholar 

  74. R. Gealageas, N. P. Malikova, S. Picaud, A. J. Borgdorff, L. P. Burakova, P. Brulet, E. S. Vysotski, R. H. Dodd, Anal. Bioanal. Chem., 2014, 406, 2695–2707.

    Article  CAS  PubMed  Google Scholar 

  75. G. A. Stepanyuk, J. Unch, N. P. Malikova, S. V. Markova, J. Lee, E. S. Vysotski, Anal. Bioanal. Chem., 2010, 398, 1809–1817.

    Article  CAS  PubMed  Google Scholar 

  76. K. Wood, E. Hawkins, M. Scurria and D. Klaubert, US Pat., WO03040100A1, 2003.

    Google Scholar 

  77. M. Otto-Duessel, V. Khankaldyyan, I. Gonzalez-Gomez, M. C. Jensen, W. E. Laug, M. Rosol, Mol. Imaging, 2006, 5, 57–64.

    Article  PubMed  Google Scholar 

  78. K. Saito, Y. F. Chang, K. Horikawa, N. Hatsugai, Y. Higuchi, M. Hashida, Y. Yoshida, T. Matsuda, Y. Arai, T. Nagai, Nat. Commun., 2012, 3, 1262.

    Article  PubMed  CAS  Google Scholar 

  79. V. Baubet, H. Le Mouellic, A. K. Campbell, E. Lucas-Meunier, P. Fossier, P. Brulet, Proc. Natl. Acad. Sci. U. S. A., 2000, 97, 7260–7265.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  80. H. Hoshino, Y. Nakajima, Y. Ohmiya, Nat. Methods, 2007, 4, 637–639.

    Article  CAS  PubMed  Google Scholar 

  81. J. Levi, A. De, Z. Cheng, S. S. Gambhir, J. Am. Chem. Soc., 2007, 129, 11900–11901.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  82. A. Takai, M. Nakano, K. Saito, R. Haruno, T. M. Watanabe, T. Ohyanagi, T. Jin, Y. Okada, T. Nagai, Proc. Natl. Acad. Sci. U. S. A., 2015, 112, 4352–4356.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  83. E. Lindberg, S. Mizukami, K. Ibata, A. Miyawaki, K. Kikuchi, Chem.–Eur. J., 2013, 19, 14970–14976.

    Article  CAS  PubMed  Google Scholar 

  84. US Pat, WO 20120614477 A1, 2012.

  85. E. Lindberg, S. Mizukami, K. Ibata, T. Fukano, A. Miyawaki, K. Kikuchi, Chem. Sci., 2013, 4, 4395–4400.

    Article  CAS  Google Scholar 

  86. R. Uchiyama, H. Tsutsui, Arch. Immunol. Ther. Exp., 2015, 63, 1–13.

    Article  CAS  Google Scholar 

  87. S. Shalini, L. Dorstyn, S. Dawar, S. Kumar, Cell Death Differ., 2015, 22, 526–539.

    Article  CAS  PubMed  Google Scholar 

  88. W. Wu, J. Li, L. Chen, Z. Ma, W. Zhang, Z. Liu, Y. Cheng, L. Du, M. Li, Anal. Chem., 2014, 86, 9800–9806.

    Article  CAS  PubMed  Google Scholar 

  89. B. Ke, W. Wu, W. Liu, H. Liang, D. Gong, X. Hu, M. Li, Anal. Chem., 2016, 88, 592–595.

    Article  CAS  PubMed  Google Scholar 

  90. B. Ke, W. Wu, L. Wei, F. Wu, G. Chen, G. He, M. Li, Anal. Chem., 2015, 87, 9110–9113.

    Article  CAS  PubMed  Google Scholar 

  91. J. Li, L. Chen, W. Wu, W. Zhang, Z. Ma, Y. Cheng, L. Du, M. Li, Anal. Chem., 2014, 86, 2747–2751.

    Article  CAS  PubMed  Google Scholar 

  92. Z. F. Walls, S. V. Gupta, G. L. Amidon, K. D. Lee, Bioorg. Med. Chem. Lett., 2014, 24, 4781–4783.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  93. R. Kojima, H. Takakura, M. Kamiya, E. Kobayashi, T. Komatsu, T. Ueno, T. Terai, K. Hanaoka, T. Nagano, Y. Urano, Angew. Chem., Int. Ed., 2015, 54, 14768–14771.

    Article  CAS  Google Scholar 

  94. W. B. Porterfield, K. A. Jones, D. C. McCutcheon, J. A. Prescher, J. Am. Chem. Soc., 2015, 137, 8656–8659.

    Article  CAS  PubMed  Google Scholar 

  95. R. H. F. Wong, T. Kwong, K.-H. Yau, H. Y. Au-Yeung, Chem. Commun., 2015, 51, 4440–4442.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (MOE), School of Pharmaceutical Sciences, Shandong University, Jinan Shandong, 250012, China

    Tianyu Jiang, Lupei Du & Minyong Li

Authors
  1. Tianyu Jiang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Lupei Du
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Minyong Li
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Minyong Li.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Jiang, T., Du, L. & Li, M. Lighting up bioluminescence with coelenterazine: strategies and applications. Photochem Photobiol Sci 15, 466–480 (2016). https://doi.org/10.1039/c5pp00456j

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1039/c5pp00456j

Search

Navigation