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Published on: September 13, 2013
Bio-orthogonally activated tetraphenylene-tetrazine aggregation-induced emission fluorogenic probes
Yu Teng1, Rongrong Zhang1, Bingbing Yang2
1Key Laboratory of Bioactive Substances and Function of Natural Medicine, Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing, 100050, China. tianyulin@imm.ac.cn.
Novel tetrazine-modified tetraphenylene (TPE) probes overcome aggregation-caused quenching (ACQ) issues in bioimaging. These probes exhibit aggregation-induced emission (AIE) and enable mitochondria-specific bio-orthogonal imaging in live cells.
Area of Science:
- Organic Chemistry
- Biomedical Imaging
- Materials Science
Background:
- Tetrazine-based probes are valuable for bioimaging but often suffer from aggregation-caused quenching (ACQ).
- Aggregation-induced emission (AIE) probes offer advantages but require careful design to avoid quenching mechanisms.
Purpose of the Study:
- To develop novel tetrazine-modified tetraphenylene (TPE) probes with aggregation-induced emission (AIE) properties for bio-orthogonal imaging.
- To overcome the ACQ limitations of existing tetrazine probes and achieve enhanced fluorescence activation.
Main Methods:
- Synthesis of novel tetrazine-modified tetraphenylene (TPE) derivatives.
- Investigation of photophysical properties, including fluorescence, AIE, and quenching mechanisms (TBET).
- Application of probes for mitochondria-specific bio-orthogonal imaging in live cells using an organelle-pretargeting strategy.
Main Results:
- Tetrazine modification quenched both fluorescence and AIE, which was reactivated via the inverse electron-demand Diels-Alder (iEDDA) reaction.
- Activated probes showed enhanced fluorescence, large Stokes shift, high quantum yield, and AIE features.
- Bi-tetrazyl probes exhibited higher turn-on ratios, and macrocycle formation was observed with double-clickable linkers.
Conclusions:
- Tetrazine-modified TPEs serve as effective bio-orthogonally activated AIE fluorogenic probes.
- The developed probes enable mitochondria-specific bio-orthogonal imaging in live cells under no-wash conditions.
- These probes represent a powerful new tool for biomedical applications.
