Synthesis and bioluminescence of electronically modified and rotationally restricted colour-shifting infraluciferin analogues |
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Authors: | James C. Anderson Chia-Hao Chang Amit P. Jathoul Aisha J. Syed |
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Affiliation: | 1. Department of Chemistry, University College London, 20 Gordon Street, London, WC1H 0AJ, UK;2. School of Biosciences, University of Cardiff, Sir Martin Evans Building, Museum Avenue, Cardiff, CF10 3AX, UK |
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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 π-extended luciferins can increase bioluminescence activity while maintaining nIR bioluminescence. |
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Keywords: | Infraluciferin Bioluminescence Near infrared Synthesis Colour shifting |
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