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

RSC Advances
James C AndersonLaurence Tisi

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.

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Citations

Feb 1, 2018·Chembiochem : a European Journal of Chemical Biology·Brendan S ZhangJennifer A Prescher
Aug 19, 2020·Physical Chemistry Chemical Physics : PCCP·Anand M PatelHelen H Fielding
Jun 8, 2018·Current Opinion in Chemical Biology·Zi YaoJennifer A Prescher
Aug 14, 2020·Journal of the American Chemical Society·Zi YaoJennifer A Prescher
Oct 9, 2019·Accounts of Chemical Research·Sierra J Williams, Jennifer A Prescher
Jul 27, 2017·Biochemistry·Colin M Rathbun, Jennifer A Prescher

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Methods Mentioned

BETA
column chromatography
Fluorescence
NMR

Software Mentioned

PhotonIMAGER Optima

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