The detection of specific supramolecular interactions in vivo has been a formidable challenge due to the limited number of assays that can probe self-assembly and molecular recognition in competitive and complex biological media. Firefly luciferin has been widely utilized as an in vivo reporter because of its selective enzyme catalysis and high quantum yield when oxidized in the presence of adenosine triphosphate and magnesium cations. Further, the emitted light is of a yellow-green color thus detection has been possible in vivo from individual cells to whole animals by a simple bioluminescence assay. Caging, or rendering the firefly luciferin molecule to be inactive for the luciferase enzyme, has been accomplished most commonly by appending electron withdrawing groups to the 6’-hydroxyl position or esterification of the thiazole moiety. The caged luciferins then undergo a reaction to yield its native, activated, form, resulting in emission of a photon upon oxidation and reporting the desired activation agent or process. The goal of our research is to use firefly luciferin as a reporter for host-guest derived supramolecular interactions by a novel method of caging, reversibly with the host molecule, cucurbituril 7. This poster will describe the synthesis and photophysical characterization of a series of firefly luciferin derivatives for use in the luciferin-luciferase type assays with the goal of detecting host-guest interactions in vivo.

Self-assembly and photophysical characterization of synthetically functionalized luciferins for detecting host-guest interactions

255th National Meeting (2018)

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