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Synthesis and bioluminescence of electronically modified and rotationally restricted colour-shifting infraluciferin analogues

Anderson, JC; Chang, CH; Jathoul, AP; Syed, AJ; (2019) Synthesis and bioluminescence of electronically modified and rotationally restricted colour-shifting infraluciferin analogues. Tetrahedron , 45 (3) pp. 347-356. 10.1016/j.tet.2018.11.061. Green open access

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Abstract

Synthetic nIR emitting luciferins can enable clearer bioluminescent imaging in blood and tissue. A limiting factor for all synthetic luciferins is their reduced light output with respect to D-luciferin. In this work we explore a design feature of whether rigidification of an exceptionally red synthetic luciferin, infraluciferin, can increase light output through a reduction in the degrees of freedom of the molecule. A rigid analogue pyridobenzimidazole infraluciferin was prepared and its bioluminescence properties compared with its non-rigid counterpart benzimidazole infraluciferin, luciferin, infraluciferin and benzimidazole luciferin. The results support the concept that synthetic rigidification of -extended luciferins can increase bioluminescence activity while maintaining nIR bioluminescence.

Type: Article
Title: Synthesis and bioluminescence of electronically modified and rotationally restricted colour-shifting infraluciferin analogues
Open access status: An open access version is available from UCL Discovery
DOI: 10.1016/j.tet.2018.11.061
Publisher version: https://doi.org/10.1016/j.tet.2018.11.061
Language: English
Additional information: This version is the author accepted manuscript. For information on re-use, please refer to the publisher’s terms and conditions.
Keywords: infraluciferin, bioluminescence, near infrared, synthesis, colour shifting
UCL classification: UCL
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/10062597
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