Highly selective fluorescence turn-on probe for glutathione

Lim, Soo-Yeon; Lee, Sang‐Hee; Park, Seung Bum; Kim, Hae-Jo

doi:10.1016/j.tetlet.2011.05.086

Cited by 24 publications

(8 citation statements)

References 24 publications

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“…61,121,126 Moreover probes with emission changes upon addition thiols will be used for cell imaging and protein labeling. 73,74,85,[89][90][91][92][93][94][95][96][97][98][99][100]108,118,136 In addition, some near-infrared (NIR) dyes as thiol probes have the unique advantage of tracing molecular activity in vivo because NIR photons can penetrate relatively deeply into tissues with low auto-fluorescence background additionally causing less damage to biological samples. 115 Moreover many examples behave as ratiometric fluorescent probes.…”

Section: Discussionmentioning

confidence: 99%

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Thiol-addition reactions and their applications in thiol recognition

et al. 2013

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Because of the biological importance of thiols, the development of probes for thiols has been an active research area in recent years. In this review, we summarize the results of recent exciting reports regarding thiol-addition reactions and their applications in thiol recognition. The examples reported can be classified into four reaction types including 1,1, 1,2, 1,3, 1,4 addition reactions, according to their addition mechanisms, based on different Michael acceptors. In all cases, the reactions are coupled to color and/or emission changes, although some examples dealing with electrochemical recognition have also been included. The use of thiol-addition reactions is a very simple and straightforward procedure for the preparation of thiol-sensing probes.

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Section: Discussionmentioning

confidence: 99%

“…89 Derivative 37 (ref. 90) contains a coumarin group as a signaling unit, a conjugated enone as a reactive site, and an o-hydroxyl group as an activating unit via hydrogen-bonding interactions (Fig. 31).…”

Section: 2-addition Reactionsmentioning

confidence: 99%

Thiol-addition reactions and their applications in thiol recognition

et al. 2013

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“…21) [182-186]. In addition, different thiol reactive sites have replaced the maleimide group to increase the rate of reaction.…”

Section: Fluorescent Sensors For Intracellular Detection Of Small mentioning

confidence: 99%

“…Recently, two probes, 47 and 48 , were designed to have a ratiometric response upon reaction with biothiols. Probe 47 reacts with GSH and Cys to afford a ratiometric change in its excitation maximum from 434 to 404 nm while increasing its fluorescence emission at 480 nm [186]. A slight modification to the backbone produces probe 48 , which experiences ratiometric changes to both its excitation and emission spectra upon reaction with GSH, Cys and Hcy [185].…”

Section: Fluorescent Sensors For Intracellular Detection Of Small mentioning

confidence: 99%

Probing oxidative stress: Small molecule fluorescent sensors of metal ions, reactive oxygen species, and thiols

Hyman

Franz

2012

Coordination Chemistry Reviews

303

211

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Oxidative stress is a common feature shared by many diseases, including neurodegenerative diseases. Factors that contribute to cellular oxidative stress include elevated levels of reactive oxygen species, diminished availability of detoxifying thiols, and the misregulation of metal ions (both redox-active iron and copper as well as non-redox active calcium and zinc). Deciphering how each of these components interacts to contribute to oxidative stress presents an interesting challenge. Fluorescent sensors can be powerful tools for detecting specific analytes within a complicated cellular environment. Reviewed here are several classes of small molecule fluorescent sensors designed to detect several molecular participants of oxidative stress. We focus our review on describing the design, function and application of probes to detect metal cations, reactive oxygen species, and intracellular thiol-containing compounds. In addition, we highlight the intricacies and complications that are often faced in sensor design and implementation.

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“…and 91 (S. Y. Lim et al, 2011) with a hydrogen bond act as highly selective ratiometric fluorescence turn-on probes for GSH. Structure 92 has been judiciously designed and synthesized as a new type of selective benzenethiol fluorescent probe based on the thiolysis of dinitrophenyl ether (Lin et al, 2010a).…”

Section: Coumarin-derived Fluorescent Chemosensors For Thiolsmentioning

confidence: 99%