Rhodamine-based fluorescent probe for highly selective detection of glutathione over cysteine and homocysteine

Hou, Xufeng; Guo, Xinling; Chen, Bing; Liu, Chunhui; Gao, Fan; Zhao, Jin; Wang, Jianghong

doi:10.1016/j.snb.2014.12.009

Cited by 58 publications

(12 citation statements)

References 37 publications

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“…[35][36][37][38][39][40][41][42][43] However, to the best of our knowledge, rhodamine B-based fluorescent probes for GSH are still rare. [44] Herein, we report the synthesis and characterization of a new rhodamine B-derivatized fluorescent chemosensor based on a maleimide moiety ,namely N-(2-(3',6'-bis(diethylamino)-3-oxospiro[isoindoline-1,9'-xanthen] -2-yl)ethyl)-3,5-bis(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzamide (Probe-M, Figure 1). The maleimide moiety and its derivatives are widely reported to be an active reaction site for the small-molecule thiols in the Michael addition reaction mechanism of the maleimide with the thiol group.…”

Section: Introductionmentioning

confidence: 99%

Design and synthesis of a new rhodamine B-based fluorescent probe for selective detection of glutathione and its application for live cell imaging

Shu

Zhou

et al. 2016

Sensors and Actuators B: Chemical

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Section: Introductionmentioning

confidence: 99%

Design and synthesis of a new rhodamine B-based fluorescent probe for selective detection of glutathione and its application for live cell imaging

Shu

Zhou

et al. 2016

Sensors and Actuators B: Chemical

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“…The fluorescent off stage is due to the quenching behavior of the electron withdrawing group through intramolecular charge transfer (ICT) process or photo‐induced charge transfer process (PCT). 2,4‐dinitrobenzenesulfonyl, thalimide, and acroyl groups have been utilized as a quencher for off‐on fluorescent probe synthesis . The on fluorescent is achieved through a reaction of thiol containing molecules with a probe utilizing some of chemical reactions such as nucleophilic substitution, redox reactions of metal complexes, GSH‐sensitive bond broken reactions, and Michael reactions.…”

Section: Introductionmentioning

confidence: 99%

1,3,5‐Triphenylpyrazoline Based Fluorescent Probe for Selective Sensing and Imaging of Glutathione in Live Cell under Oxidative Stress

et al. 2020

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Herein, a facile method to synthesize the fluorescence probe 1‐(4‐(1,5‐diphenyl‐4,5‐dihydro‐1H‐pyrazol‐3‐yl)phenyl)‐1H‐pyrrole‐2,5‐dione (probe 10) was reported. The relative quantum yield determined using quinine sulfate for the probe 10 is 42% in 100% acetonitrile (ACN), which was reduced to 6% in 10% ACN‐water system. The turn‐off probe 10 becomes turn‐on selectively in the presence of glutathione (GSH). The Probe 10 is highly sensitive to GSH in the presence of common interfering molecules like cysteine, N‐acetylcysteine, thioglycolic acid, mercaptoethanol, and mercaptopropionoic acid. The limit of detection is 0.06 μM. The practical use of the probe 10 was demonstrated through quantifying GSH (1.68 mM) in the blood serum of healthy person, artificial cerebrospinal fluid, and artificial urine. Probe 10 works on a wide range of pH 2–12. Cells expressing GSH can be imaged using probe 10 and also useful in analysing the percentage of GSH in the cells under oxidative stress.

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“…We have developed as eries of fluorescent probes, which exhibited satisfactory sensitivity and selectivity. [37][38][39][40] Resorufin is af luorescent molecular with excellent chromogenic and fluorogenic signaling behaviors. When the hydroxyl of resorufin was protected, it showedn early no fluorescence.…”

Section: Introductionmentioning

confidence: 99%

“…Our group has focused on developing fluorescence probes and the design strategies are reaction‐based between the recognition groups and biologically biomarkers. We have developed a series of fluorescent probes, which exhibited satisfactory sensitivity and selectivity . Resorufin is a fluorescent molecular with excellent chromogenic and fluorogenic signaling behaviors.…”

Section: Introductionmentioning

confidence: 99%

A Reaction‐Based Fluorescent Probe for Imaging of Native Hypochlorous Acid

Wang

Men

Niu

et al. 2019

Chemistry An Asian Journal

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Hypochlorousa cid (HOCl), one of the reactive oxygen species( ROS), is highly reactive and short-lived. It is ac hallenge to dynamic monitorH OCl activity in living systems. Hence, we synthesized an ew fluoresce nt probe RF1 based on protection of the hydroxyl group by N,N-dimethylthiocarbamate recognition group, which reached al ow fluorescence background signal and highly sensitivep roperty.O na ccount of the electrophilica ddition of Cl + to the sul-fide of thiocarbamate moiety,p robe RF1 was converted to resorufin and triggered emitting bright. RF1 showed not only the highlys ensitive and selective response to HOCl in vitro, but also can be applied in environmental water samples and detected HOCl by test strips. Besides, the ability of RF1 monitoring HOCl in HeLa cells by exogenous simulation and tracingn ative HOCl in macrophages cells were also explored.[a] Dr.

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Rhodamine-based fluorescent probe for highly selective detection of glutathione over cysteine and homocysteine

Cited by 58 publications

References 37 publications

Design and synthesis of a new rhodamine B-based fluorescent probe for selective detection of glutathione and its application for live cell imaging

Design and synthesis of a new rhodamine B-based fluorescent probe for selective detection of glutathione and its application for live cell imaging

1,3,5‐Triphenylpyrazoline Based Fluorescent Probe for Selective Sensing and Imaging of Glutathione in Live Cell under Oxidative Stress

A Reaction‐Based Fluorescent Probe for Imaging of Native Hypochlorous Acid

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