Abstract: Bioluminescence in vivo imaging has rapidly developed into a highly useful tool to study diseases and evaluate potential therapeutic agents. There remains, however, an inherent need for improving the sensitivity and resolution of the images obtained with this technique. This can, in principle, be accomplished by modifying known beetle luciferases through mutagenesis and synthesizing new luciferin analogs to produce near-Infrared (nIR) light. This is because nIR radiation enables deeper imaging due to lower scattering and better penetration through hemoglobin and other interferents. We have focused on increasing the nIR emission of beetle luciferases by extending the conjugation of the natural substrate by synthesizing quinoline-based luciferin analogs that contain electron donating amino groups at various positions on the heterocyclic ring. To date, we have prepared and evaluated 3 novel analogs. One of these new reagents displayed a broad emission (118 nm bandwidth) with a 688 nm maximum when assayed with a variant of click beetle red luciferase. Moreover, the intensity of the emission in vitro exceeded that of a similar naphthalene-based analog. The synthetic pathways to the analogs and full photophysical characterization will be presented, along with the results of in vitro bioluminescence testing.

Bioluminescent studies of quinoline-based amino analogs of firefly luciferin

2019 Fall National Meeting

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