Coumarin-based thiol chemosensor: Synthesis, turn-on mechanism, and its biological application

Hyo Sung Jung; Kyoung Chul Ko; Gun Hee Kim; Ah Rah Lee; Yun Cheol Na; Chulhun Kang; Jin Yong Lee; Jong Seung Kim

doi:10.1021/ol2001864

Coumarin-based thiol chemosensor: Synthesis, turn-on mechanism, and its biological application

Hyo Sung Jung, Kyoung Chul Ko, Gun Hee Kim, Ah Rah Lee, Yun Cheol Na, Chulhun Kang, Jin Yong Lee, Jong Seung Kim

Research output: Contribution to journal › Article › peer-review

191 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1498-1501
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	6
DOIs	https://doi.org/10.1021/ol2001864
Publication status	Published - 2011 Mar 18

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol2001864

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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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AU - Jung, Hyo Sung

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AU - Kim, Gun Hee

AU - Lee, Ah Rah

AU - Na, Yun Cheol

AU - Kang, Chulhun

AU - Lee, Jin Yong

AU - Kim, Jong Seung

PY - 2011/3/18

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Coumarin-based thiol chemosensor: Synthesis, turn-on mechanism, and its biological application

Abstract

ASJC Scopus subject areas

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