A coumarin–Meldrum's acid conjugate based chemodosimetric probe for cyanide

Li, Hongda; Wang, Zhi; Jin, Longyi; Kan, Yu‐He; Yin, Bo

doi:10.1039/c2cc36838b

Cited by 58 publications

(14 citation statements)

References 32 publications

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“…1d). Under pseudo-first-order kinetic conditions, 23 the observed rate constant (K obs ) for Cys, Hcy and GSH were determined as 0.241 ± 0.010, 0.238 ± 0.007, and 0.143 ± 0.006 min −1 , respectively (Fig. S2, ESI).…”

Section: Resultsmentioning

confidence: 99%

A dual emission fluorescent probe enables simultaneous detection of glutathione and cysteine/homocysteine

et al. 2014

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Many studies have shown that glutathione (GSH) and cysteine (Cys) / homocysteine (Hcy) levels are interrelated in biological systems. To unravel the complicated biomedical mechanisms by which GSH and Cys/Hcy are involved in various disease states, probes that display distinct signals in response to GSH and Cys/Hcy are highly desirable. In this work, we report a rhodol thioester (1) that responds to GSH and Cys/Hcy with distinct fluorescence emissions in neutral media. Probe 1 reacts with Cys/Hcy to form the corresponding deconjugated spirolactam via a tandem native chemical ligation (NCL) reaction. This intramolecular spirocyclization leads to the “quinone – phenol” transduction of rhodol dyes, and an excited-state intramolecular proton transfer (ESIPT) process between the phenolic hydroxyl proton and the aromatic nitrogen in the benzothiazole unit occurs upon photoexcitation, thus affording 2-(2’-hydroxyphenyl) benzothiazole (HBT) emission (454 nm). In the case of the tripeptide GSH, only transthioesterification takes place removing the intramolecular photo-induced electron transfer (PET) process caused by the electron deficient 4-nitrobenzene moiety giving rise to a large fluorescence enhancement at the rhodol emission band (587 nm). The simultaneous detection of GSH and Cys/Hcy is attributed to the significantly different rates of intramolecular S,N-acyl shift of their corresponding thioester adducts derived from 1. The utility of probe 1 has been demonstrated in various biological systems including serum and cells.

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Section: Resultsmentioning

confidence: 99%

A dual emission fluorescent probe enables simultaneous detection of glutathione and cysteine/homocysteine

et al. 2014

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“…So the calculations results are in good agreement with the experimental results. 15,16 In summary, we have successfully developed a new ratiometric uorescent sensor for the detection of CN À . DFT and TD-DFT calculations suggested the sensing mechanism.…”

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confidence: 96%

A new colorimetric fluorescent sensor for ratiometric detection of cyanide in solution, test strips, and in cells

et al. 2014

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A new high selective and sensitive fluorescent sensor for the detection of cyanide was developed based on the nucleophilic attack of CN À with a color change from purple to colourless. The chemosensor was used for fabrication of test strips that can detect cyanide in aqueous samples. The living animal fluorescence experiment demonstrated the practical value of the sensor in tracing the CN À in biological systems.

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“…Furthermore, S 2− , CO 3 2− , ACO − , S 2 O 3 2− , SO 4 2− , I − , Br − , Cl − , H 2 PO 4 − , F − , SCN − , NO 2 − , glutathione (GSH), homocysteine (Hcy) and cysteine (Cys) were selected as interference ions to evaluate the selectivity of SY 15 22 . As shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

“…With a similar mechanism, Shiraishi et al recently synthesised a new fluorescent probe to selectively and sensitively detect CN − 15 . Most of these probes are designed on ON-OFF and OFF-ON mechanisms 16 17 18 19 20 21 , wherein detection depends only on the changes in single emission and might be affected by external factors including excitation power, detector sensitivity and environment 22 .…”

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confidence: 99%

Ratiometric and colorimetric near-infrared sensors for multi-channel detection of cyanide ion and their application to measure β-glucosidase

Xing

et al. 2015

Sci Rep

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A near-infrared sensor for cyanide ion (CN−) was developed via internal charge transfer (ICT). This sensor can selectively detect CN− either through dual-ratiometric fluorescence (logarithm of I414/I564 and I803/I564) or under various absorption (356 and 440 nm) and emission (414, 564 and 803 nm) channels. Especially, the proposed method can be employed to measure β-glucosidase by detecting CN− traces in commercial amygdalin samples.

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A coumarin–Meldrum's acid conjugate based chemodosimetric probe for cyanide

Abstract: A highly reactive and selective chemodosimetric probe for cyanide was synthesized based on alkylidene Meldrum's acid as a novel cyanide reaction site. A theoretical study was conducted to rationalize the high reactivity and the photophysical properties of probe 1 and the 1-CN adduct.

Cited by 58 publications

References 32 publications

A dual emission fluorescent probe enables simultaneous detection of glutathione and cysteine/homocysteine

A dual emission fluorescent probe enables simultaneous detection of glutathione and cysteine/homocysteine

A new colorimetric fluorescent sensor for ratiometric detection of cyanide in solution, test strips, and in cells

Ratiometric and colorimetric near-infrared sensors for multi-channel detection of cyanide ion and their application to measure β-glucosidase

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