In recent years, bioorthogonal reactions have been widely used on live-cell labeling, animal tissue imaging, drug delivery, and biomaterial applications. Tetrazine bioorthogonal reactions, as one of most powerful tools in the kit, have attracted a lot of interest. Herein, we showcase a series of highly fluorogenic probes based on tetrazine bioorthogonal chemistry. We first developed an elimination-Heck cascade reaction for alkenyl-tetrazine synthesis. By using this strategy, several kinds of highly conjugated probes have been obtained, including Oregon Green, orange Rhodamine, and Bodipy scaffolds. Very recently, we developed another tetrazine bioorthogonal reaction. Blue and near infrared fluorophores can be fully quenched by caging the conjugation with a reactive dienophile group. After reacting with a tetrazine, the cage opens resulting in a fluorescence increase greater than 100-fold. With this chemistry, a full spectrum of turn-on probes have been achieved with a common fluorogenic bioorthogonal reaction. By using these probes, exciting applications have been demonstrated such as cell surface labeling and endogenous oncogenic miRNA detection. Additionally, we have been able to convert turn-over probes into a turn-on hybridization reporter for live cell mRNA imaging. We believe these probes will have wide applications in future studies such as whole tissue imaging and multi-color co-localization investigations with multiple RNA of interest.

Full-spectrum fluorogenic tetrazine bioorthogonal probes for live-cell imaging

251st National Meeting (2016)

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