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Tetrazine-based cycloadditions: application to pretargeted live cell imaging.


ABSTRACT: Bioorthogonal tetrazine cycloadditions have been applied to live cell labeling. Tetrazines react irreversibly with the strained dienophile norbornene forming dihydropyrazine products and dinitrogen. The reaction is high yielding, selective, and fast in aqueous media. Her2/neu receptors on live human breast cancer cells were targeted with a monoclonal antibody modified with a norbornene. Tetrazines conjugated to a near-infrared fluorochrome selectively and rapidly label the pretargeted antibody in the presence of serum. These findings indicate that this chemistry is suitable for in vitro labeling experiments, and suggests that it may prove a useful strategy for in vivo pretargeted imaging under numerous modalities.

SUBMITTER: Devaraj NK 

PROVIDER: S-EPMC2677645 | biostudies-literature | 2008 Dec

REPOSITORIES: biostudies-literature

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Tetrazine-based cycloadditions: application to pretargeted live cell imaging.

Devaraj Neal K NK   Weissleder Ralph R   Hilderbrand Scott A SA  

Bioconjugate chemistry 20081201 12


Bioorthogonal tetrazine cycloadditions have been applied to live cell labeling. Tetrazines react irreversibly with the strained dienophile norbornene forming dihydropyrazine products and dinitrogen. The reaction is high yielding, selective, and fast in aqueous media. Her2/neu receptors on live human breast cancer cells were targeted with a monoclonal antibody modified with a norbornene. Tetrazines conjugated to a near-infrared fluorochrome selectively and rapidly label the pretargeted antibody i  ...[more]

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