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

Anderson, James C., Grounds, Helen, Jathoul, Amit ORCID: https://orcid.org/0000-0002-6767-7775, Murray, James Augustus Henry ORCID: https://orcid.org/0000-0002-2282-3839, Pacman, Steven J. and Tisi, Laurence 2016. Convergent synthesis and optical properties of near-infrared emitting bioluminescent infra-luciferins. RSC Advances 7 (7) , pp. 3975-3982. 10.1039/C6RA19541E

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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.

Item Type:	Article
Date Type:	Published Online
Status:	Published
Schools:	Biosciences
Publisher:	RSC Publishing
ISSN:	2046-2069
Date of First Compliant Deposit:	16 January 2017
Date of Acceptance:	15 December 2016
Last Modified:	06 May 2023 16:06
URI:	https://orca.cardiff.ac.uk/id/eprint/97469

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