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
|
Preview |
PDF
- Published Version
Available under License Creative Commons Attribution Non-commercial. Download (709kB) | Preview |
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: | 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 |
Citation Data
Cited 23 times in Scopus. View in Scopus. Powered By Scopus® Data
Actions (repository staff only)
 |
Edit Item |
Dimensions
Dimensions