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

Anderson, James C., Grounds, Helen, Jathoul, Amit ORCID:, Murray, James Augustus Henry ORCID:, 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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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

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