Recent progress in the synthesis of firefly luciferin derivatives

Shining light on the electronic structure and relaxation dynamics of the isolated oxyluciferin anion

“…17 To date, modifications to luciferins have successfully red-shifted the light emission; however, this has come at the cost of reducing the bioluminescence quantum yield. 18 One of the research aims of our groups is to improve the fundamental understanding of bioluminescence for the rational design of new bioluminescence tools. [19][20][21][22] The focus of the work described in this paper is to improve our understanding of the electronic structure of the lightemitting oxyluciferin (OL).…”

Applications of bioluminescence in biotechnology and beyond

“…68 Some of these set-backs have been overcome with the design, synthesis and testing of novel D-luciferin analogues, which have led to brighter, red-shifted emission in some cases. 69 Details on these can be found in Section 3.1.…”

“…The chemical synthetic routes towards luciferin analogues were succinctly compiled by Podsiadly et al in 2019. 69 Herein, we briefly highlight synthetic luciferin analogues, particularly those that have found use in applications, or have useful and interesting properties such as brightness that could potentially make them useful in applications. As the primary use of red-shifted D-luciferin analogues is in in vivo applications, we particularly highlight analogues that emit in the near infra-red region (4650 nm), and of those analogues, specifically those that have been successfully tested in vivo (Table 5).…”

Modified Enzyme Substrates for the Detection of Bacteria: A Review

“…Luciferin analogues are made with the same procedure by starting from a substituted cyanobenzothiazole. The synthesis of intermediate 46 was improved over the years and several procedures are available [ 57 , 58 , 59 ], the most popular involving the dehydration of a benzothiazole amide, a Sandmeyer reaction using a cyanide source or a Michael condensation with benzoquinone [ 59 ]. An interesting synthetic route towards cyanobenzothiazole 46 was reported by Prescher et al ( Scheme 8 B), starting from the condensation of p-methoxyaniline 48 43 with Appel’s salt 44, to generate thioformamide 45.…”