期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 144, 期 43, 页码 19778-19790出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.2c06397
关键词
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资金
- JSPS KAKENHI [JP20H02701, JP21H05262, JP20H04767, JP19H05414, JP18H04609, JP16H05099, JP16H00823, JP26104509, JP20H02801, JP16H06574, JP19H05632]
- JST SENTAN
- JST Grant Moonshot R&D MILLENNIA Program [JPMJMS2022-12]
- JST-Mirai Program [JP21472174]
- Japan Agency for Medical Research and Development (AMED) [JP21ak0101182h0001, JP21wm0325046s0101, JP19dm0207080, JP21wm0425001, JP21zf0127004]
- Hoansha Foundation
- Mochida Memorial Foundation for Medical and Pharmaceutical Research
- Astellas Foundation for Research on Metabolic Disorders
- Tokyo Biochemical Research Foundation
- Nakatani Foundation for Advancement of Measuring Technologies in Biomedical Engineering
- JSPS [JPJSCCA20170007]
This study establishes a new molecular design strategy for developing activatable fluorescent probes by controlling the twisted intramolecular charge transfer process. The fluorescence off/on mechanism based on this strategy is successfully applied to the development of practical probes for HaloTag and SNAP-tag, demonstrating its generalizability to other chemical dyes.
Fluorogenic probes for bioimaging have become essential tools for life science and medicine, and the key to their development is a precise understanding of the mechanisms available for fluorescence off/on control, such as photoinduced electron transfer (PeT) and Fo''rster resonance energy transfer (FRET). Here we establish a new molecular design strategy to rationally develop activatable fluorescent probes, which exhibit a fluorescence off/on change in response to target biomolecules, by controlling the twisted intramolecular charge transfer (TICT) process. This approach was developed on the basis of a thorough investigation of the fluorescence quenching mechanism of N-phenyl rhodamine dyes (commercially available as the QSY series) by means of time dependent density functional theory (TD-DFT) calculations and photophysical evaluation of their derivatives. To illustrate and validate this TICT-based design strategy, we employed it to develop practical fluorogenic probes for HaloTag and SNAP-tag. We further show that the TICT-controlled fluorescence off/on mechanism is generalizable by synthesizing a Si-rhodamine-based fluorogenic probe for HaloTag, thus providing a palette of chemical dyes that spans the visible and near-infrared range.
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