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Coumarin-Based Thiol Chemosensor: Synthesis, Turn-On Mechanism, and Its Biological Application
- Authors
- Jung, Hyo Sung; Ko, Kyoung Chul; Kim, Gun-Hee; Lee, Ah-Rah; Na, Yun-Cheol; Kang, Chulhun; Lee, Jin Yong; Kim, Jong Seung
- Issue Date
- 18-3월-2011
- Publisher
- AMER CHEMICAL SOC
- Citation
- ORGANIC LETTERS, v.13, no.6, pp.1498 - 1501
- Indexed
- SCIE
SCOPUS
- Journal Title
- ORGANIC LETTERS
- Volume
- 13
- Number
- 6
- Start Page
- 1498
- End Page
- 1501
- ISSN
- 1523-7060
- Abstract
- A new chemodosimetric probe (1) is reported that selectively detects thiols over other relevant biological species by the turning on of its fluorescence through a Michael type reaction. The fluorogenic process upon its reaction was revealed to be mediated by intramolecular charge transfer, as confirmed by time-dependent density functional theory calculations. The application of probe 1 to cells is also examined by confocal microscopy, and its cysteine preference was observed by an ex vivo LC-MS analysis of the cellular metabolite.
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