Tohoku Univ. Technology : External stimulus responsive click reaction technology : T21-077
Controling Inverse-Electron-Demand Diels–Alder Reaction with macrocyclic tetrazine
Inverse-Electron-Demand Diels–Alder Reaction(IEDDA), a cyclization reaction between tetrazine and dienophile, is used in various fields from materials science to biological applications due to its fast reactivity and high selectivity. If this reactivity can be controlled, the application range is expected to expand dramatically. A method for controlling the reaction by oxidizing dihydrotetrazine to tetrazine, which is less reactive, has been reported, but there are problems such as the effect of natural oxidation and the inability to respond to stimuli other than oxidation. The inventors found that the IEDDA reaction can be completely suppressed by derivatizing tetrazine to a macrocyclic structure, and that the reaction proceeds rapidly when the reaction is converted from a cyclic to an acyclic structure by stimulation. The stimuli in the present invention can be selected according to the application, such as light, heat, pH, enzymatic reaction, redox, etc. By using the present invention, it is expected to be applied to the in vivo synthesis of active pharmaceuticals, environmentally responsive drug delivery systems, chemical sensors, nuclear medicine diagnostics, etc.
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The revenue generated from technology transfer is reinvested as new research funding for universities and researchers, and is utilized to create further research outcomes. To ensure the smooth operation of this cycle, known as the "Intellectual Creation Cycle," we will vigorously promote technology transfer. The types of seeds we handle include patents, know-how, databases, and programs. We have established a collaborative framework by signing basic technology transfer agreements with the following universities (as of June 1, 2025): Tohoku University, Hirosaki University, Iwate University, Akita University, Fukushima University, Yamagata University, Tohoku Gakuin University, Iwate Medical University, Fukushima Medical University, Aizu University, Miyagi University, Hokkaido University, Muroran Institute of Technology, and Showa Medical University.
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