Choi, Sang-Kee Lee, Youngjun Yoon, Sang Eun Choi, Hongseo Kim, Jonghoon Kim, Jong H. Lee, Sanghee Kim, Wook Kim, Eunha 2024-01-19T14:02:32Z 2024-01-19T14:02:32Z 2021-09-05 2021-08-01 0925-4005 https://pubs.kist.re.kr/handle/201004/116603 Bioorthogonal fluorogenic probes allow spatiotemporally controlled molecular bioimaging with minimal perturbation of the native cellular environment. Due to favorable kinetics and reaction specificity in a physiological environment, inverse electron-demand Diels - Alder reaction (iEDDA) for bioorthogonal fluorogenic bioimaging has gained immense attention in scientific field; however, the technique still needs to washout excess trans-cyclooctene labels, thereby reducing the robustness and experimental convenience. In the present study, we report tetrazine-modified aggregation-induced emission luminogens for bioorthogonal fluorogenic bioimaging. We found that a unique molecular design strategy allowed incorporation of tetrazine on aggregation-induced emission luminogens with excellent fluorogenic properties. Moreover, tetrazine modification of aggregationinduced emission luminogens results in non-radiative decay, which induces fluorescence quenching. The systematic tunability of the emission wavelength of the fluorescent core skeleton allowed successful development of three different colorful fluorogenic tetrazine-fluorophores. Furthermore, an aggregate formation study and computational calculations revealed a synergistic fluorescent quenching effect between intramolecular charge transfer and tetrazine-mediated non-radiative decay. The final simple conjugation between triphenylphosphonium and tetrazine-fluorophore enabled successful development of fluorogenic probes for spatiotemporally controlled bioorthogonal bioimaging of mitochondria in live cells with the iEDDA without washing the transcyclooctene label and tetrazine-fluorophore. English ELSEVIER SCIENCE SA INTRAMOLECULAR CHARGE-TRANSFER ENERGY-TRANSFER CASSETTES CELLULAR HETEROGENEITY FLUORESCENCE CYCLOADDITION MITOCHONDRIA MOLECULES PROBES A tetrazine-fused aggregation induced emission luminogen for bioorthogonal fluorogenic bioprobe Article 10.1016/j.snb.2021.129966 1 SENSORS AND ACTUATORS B-CHEMICAL, v.340 SENSORS AND ACTUATORS B-CHEMICAL 340 scie scopus 000652615300004 2-s2.0-85104593117 Chemistry, Analytical Electrochemistry Instruments & Instrumentation Chemistry Electrochemistry Instruments & Instrumentation Article INTRAMOLECULAR CHARGE-TRANSFER ENERGY-TRANSFER CASSETTES CELLULAR HETEROGENEITY FLUORESCENCE CYCLOADDITION MITOCHONDRIA MOLECULES PROBES Aggregation-induced emission Tetrazine Fluorogenic Click chemistry