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Tetrazine reactive dyes can be used to label ring-tensioned olefins (such as cyclooctene, trans-cyclooctene) and other activated olefins through the Diels-Alder reaction. The trans-Diels-Alder reaction of cyclic tension olefin and tetrazine is the fastest known bio-orthogonal reaction, which could be used for protein labeling in real-time.
A bioorthogonal reaction is a type of chemical reaction that can be carried out in living cells. This type of reaction has the following characteristics: (1) It can occur under physiological conditions; (2) The reaction is highly efficient and specific; (3) It does not interfere with other biochemical reactions that occur simultaneously in the body (4) The reaction speed is fast; (5) The reaction is not toxic; (6) There is no side reaction.
The Diels-Alder reaction is a cycloaddition reaction involving conjugated dienes and substituted olefins. Diels-Alder reaction is a kind of bioorthogonal reaction without catalyst. Tetrazine is a class of electron-deficient heterocyclic compounds with reversible electroactivity, and its photochemical and electrochemical properties are active. Tetrazine can produce Diels-Alder reaction of inverse electron demand very quickly and efficiently with olefins or alkynes with ring tension.
Tetraazine reactive dyes can fluorescently label molecules labeled with cyclic tension olefins. Tetrazine can quench the fluorescence emitted at the wavelength of 510-570 nm. But when the cycloolefin reacts with such tetrazine, the fluorescence will be restored. This phenomenon of fluorescence quenching and regeneration can monitor protein movement in real-time. The reaction of cyclic tension olefins and tetrazine can be used for protein labeling in various buffer solutions in vitro, as well as labeling in vivo. The reaction between cyclic tension olefins and tetrazine has been successfully applied to many applications such as antibody labeling, protein modification, and super-resolution imaging.