Jump to main content
Jump to site search

Issue 7, 2017
Previous Article Next Article

Convergent synthesis and optical properties of near-infrared emitting bioluminescent infra-luciferins

Author affiliations

Abstract

Infra-luciferin, an alkene linked analogue of luciferin, gives bioluminescence emission >700 nm and has the potential to be used for multiparametric in vivo imaging. We report here a high yielding, scalable and convergent synthesis of infra-luciferin which will allow the synthesis of other conjugated luciferins for investigation in near-infrared bioluminescence imaging. We demonstrated this potential by using the new route to synthesise a diene linked analogue of luciferin, the fluorescent and bioluminescent properties of which were compared to those of D-luciferin and infra-luciferin. We found that extension of conjugation to a diene linker resulted in the specific bioluminescence activity being reduced by 3–4 orders of magnitude compared to D-luciferin. Analogous to its fluorescence emission spectrum, the diene linked analogue exhibited two peaks in its bioluminescence spectrum, the major one being slightly blue-shifted compared to natural D-luciferin, and a minor peak at ca. 800 nm. The fluorescence quantum yield and pH dependence of fluorescence were also determined.

Graphical abstract: Convergent synthesis and optical properties of near-infrared emitting bioluminescent infra-luciferins

Back to tab navigation

Supplementary files

Publication details

The article was received on 02 Aug 2016, accepted on 15 Dec 2016 and first published on 20 Dec 2016


Article type: Paper
DOI: 10.1039/C6RA19541E
Author version
available:
Download author version (PDF)
RSC Adv., 2017,7, 3975-3982
  • Open access: Creative Commons BY license
  •   Request permissions

    Convergent synthesis and optical properties of near-infrared emitting bioluminescent infra-luciferins

    J. C. Anderson, H. Grounds, A. P. Jathoul, J. A. H. Murray, S. J. Pacman and L. Tisi, RSC Adv., 2017, 7, 3975
    DOI: 10.1039/C6RA19541E

    This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements