Journal
RSC ADVANCES
Volume 7, Issue 7, Pages 3975-3982Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6ra19541e
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Funding
- EPSRC [EP/L504889/1]
- Wellcome Trust ISSF [510263]
- UCL
- BBSRC [BB/L022346/1] Funding Source: UKRI
- Biotechnology and Biological Sciences Research Council [BB/L022346/1] Funding Source: researchfish
- Engineering and Physical Sciences Research Council [1452869] Funding Source: researchfish
- National Centre for the Replacement, Refinement and Reduction of Animals in Research (NC3Rs) [NC/N00339X/1] Funding Source: researchfish
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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.
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