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조회370

손하영Hayoung Son

서울대학교

Angew. Chem.-Int. Edit., Nov 29 2024, | https://doi.org/10.1002/anie.202421982 Unveiling the Structure-Fluorogenic Property Relationship of Seoul-Fluor-Derived Bioorthogonal Tetrazine Probes

Hayoung Son^‡, Dahham Kim^‡, Sohee Kim, Wan Gi Byun, and Seung Bum Park^*

^[*]H. Son, Dr. D. Kim, S. Kim, Dr. W. G. Byun, and Prof. Dr. S. B. Park.
Department of Chemistry, Seoul National University, Seoul 08826 (Korea)
^[‡]These authors contributed equally to this work.

Corresponding Author : Seung Bum Park

Abstract

Tetrazine (Tz)-embedded fluorescent probes, known for their fluorogenicity following bioorthogonal inverse electron-demand Diels-Alder (iEDDA) reactions, are extensively used in bioimaging. Despite significant research on fluorogenic Tz probes, there has been limited systematic exploration of their fluorogenic responses with various dienophiles. In this study, we elucidate the structure-fluorogenic property relationship of bioorthogonal Tz probes. We synthesized a series of Seoul-Fluor-Tz (SFTz) probes designed to exhibit differentiated turn-on fluorescence upon iEDDA reactions with three dienophiles: trans-cyclooctene (TCO), bicyclo[6.1.0]nonyne (BCN), and spiro[2.3]hex-1-ene (Sph). Our findings revealed that the fluorogenic properties of the SFTz probes are highly dependent on the structures of dienophile-Tz adducts. By systematically modifying the electronic properties and employing quantum chemical calculations, we developed a series of SFTz probes with optimal dienophile-dependent fluorescence. These probes enabled simultaneous dual-color imaging of different cellular targets using a single probe, providing a robust approach for advanced bioimaging applications that require precise and efficient multicolor labeling strategies.

논문정보

형식Research article
게재일2024년 11월 (BRIC 등록일 2024-12-02)
연구진국내 연구진
분야 생명과학 > 분자생물학

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