Citation: Xiang Li, Hong Yang, Yu Teng, Yongcheng Wang, Dali Yin, Yulin Tian. A general strategy for in situ assembly of light-up fluorophores via bioorthogonal Suzuki-Miyaura cross-coupling[J]. Chinese Chemical Letters, ;2022, 33(9): 4223-4228. doi: 10.1016/j.cclet.2022.03.008 shu

A general strategy for in situ assembly of light-up fluorophores via bioorthogonal Suzuki-Miyaura cross-coupling

Key Laboratory of Bioactive Substances and Function of Natural Medicine, Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China

tianyulin@imm.ac.cn

Received Date: 13 September 2021
Revised Date: 21 February 2022
Accepted Date: 2 March 2022
Available Online: 4 March 2022

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Herein we presented a general strategy for in situ assembly of intramolecular charge-transfer (ICT)-based light-up fluorophores via bioorthogonal Suzuki-Miyaura cross-coupling reaction. By introducing iodo group at the appropriate position, five fluorophores with different scaffolds including naphthalimide, coumarin, naphthalene sulfonate, nitrobenzoxadiazole, and acetonaphthone, were designed as bioorthogonal multicolor fluorogenic probes, which could produce significant fluorescence enhancement and high fluorescence quantum yield after Suzuki-Miyaura reaction with aryl boronic acid or boronate. Manipulating the substituents and π scaffold in the fluorophores allows fine-tuning of their photophysical properties. With this strategy, we succeeded in peptide conjugation, no-wash fluorogenic protein labeling, and mitochondria-selective bioorthogonal imaging in live cells.
- Bioorthogonal reaction,
- Suzuki-Miyaura cross-coupling,
- Fluorogenic probes,
- Naphthalimide,
- Live-cell imaging
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