Chang, Chia-Hao;
Fontaine, Danielle M;
Gomez, Sandra;
Branchini, Bruce R;
Anderson, James C;
(2023)
Synthesis and Bioluminescence of 'V'-Shaped Firefly Luciferin Analogues Based on A Novel Benzobisthiazole Core.
Chemistry - A European Journal
, 29
(69)
, Article e202302204. 10.1002/chem.202302204.
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Abstract
The design of π-extended conjugation ‘V‘-shaped red shifted bioluminescent D-luciferin analogues based on a novel benzobisthiazole core is described. The divergent synthetic route allowed access to a range of amine donor substituents through an S<inf>N</inf>Ar reaction. In spectroscopic studies, the ‘V’-shaped luciferins exhibited narrower optical band gaps, more red-shifted absorption and emission spectra than D-luciferin. Their bioluminescence characteristics were recorded against four different luciferases (PpyLuc, FlucRed, CBR2 and PLR3). With native luciferase PpyLuc, the ‘V’-shaped luciferins demonstrated more red-shifted emissions than D-luciferin (λ<inf>bl</inf>=561 nm) by 60 to 80 nm. In addition, the benzobisthiazole luciferins showed a wide range of bioluminescence spectra from the visible light region (λ<inf>bl</inf>=500 nm) to the nIR window (>650 nm). The computational results validate the design concept which can be used as a guide for further novel D-luciferin analogues based upon other ‘V’-shaped heterocyclic cores.
| Type: | Article |
|---|---|
| Title: | Synthesis and Bioluminescence of 'V'-Shaped Firefly Luciferin Analogues Based on A Novel Benzobisthiazole Core |
| Location: | Germany |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1002/chem.202302204 |
| Publisher version: | https://doi.org/10.1002/chem.202302204 |
| Language: | English |
| Additional information: | © 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
| 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/10216302 |
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