Issue 7, 2017

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

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

Supplementary files

Article information

Article type
Paper
Submitted
02 Aug 2016
Accepted
15 Dec 2016
First published
20 Dec 2016
This article is Open Access
Creative Commons BY license

RSC Adv., 2017,7, 3975-3982

Author version available

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

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