Fluorescent coumarin-based probe for cysteine and homocysteine with live cell application

Wei, Ling Fang; Thirumalaivasan, Natesan; Liao, Yu Kuang; Wu, Shu-Pao

doi:10.1016/j.saa.2017.04.051

Cited by 23 publications

(7 citation statements)

References 39 publications

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“…Acrylesters and acrylamides also have been used as biothiol-selective masking groups for various fluorophores. Acrylesters 306 – 310 − all show very similar behavior, with a good selectivity for Cys over GSH and Hcy. The selectivity in function of the thiol nucleophilicity is further enhanced by a cyclization reaction of the amino group of Cys, leading to the liberation of the corresponding umbelliferone analogue (Figure ).…”

Section: Fluorescent Chemosensors Based On Coumarin Platform For Biol...mentioning

confidence: 98%

Coumarin-Based Small-Molecule Fluorescent Chemosensors

et al. 2019

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Coumarins are a very large family of compounds containing the unique 2H-chromen-2-one motif, as it is known according to IUPAC nomenclature. Coumarin derivatives are widely found in nature, especially in plants and are constituents of several essential oils. Up to now, thousands of coumarin derivatives have been isolated from nature or produced by chemists. More recently, the coumarin platform has been widely adopted in the design of small-molecule fluorescent chemosensors because of its excellent biocompatibility, strong and stable fluorescence emission, and good structural flexibility. This scaffold has found wide applications in the development of fluorescent chemosensors in the fields of molecular recognition, molecular imaging, bioorganic chemistry, analytical chemistry, materials chemistry, as well as in the biology and medical science communities. This review focuses on the important progress of coumarin-based small-molecule fluorescent chemosensors during the period of 2012− 2018. This comprehensive and critical review may facilitate the development of more powerful fluorescent chemosensors for broad and exciting applications in the future.

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Section: Fluorescent Chemosensors Based On Coumarin Platform For Biol...mentioning

confidence: 98%

Coumarin-Based Small-Molecule Fluorescent Chemosensors

et al. 2019

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“…The acrylate group has been applied as a thiols reaction site for detecting thiols [ 53 , 54 ]. Based on the reported conjugate addition/cyclization sensing mechanism, the mechanism of probe responding to Cys involved the next two steps: the conjugate addition of Cys to an unsaturated carbonyl moiety generated thioether ( 1a ), followed by intramolecular cyclization that gave the desired compound 1 , which was responsible for the enhancement of the fluorescence intensity.…”

Section: Resultsmentioning

confidence: 99%

A Fluorescent Coumarin-Based Probe for the Fast Detection of Cysteine with Live Cell Application

Zeng

Lan

et al. 2017

Molecules

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A new coumarin-based fluorescent probe, containing an allylic esters group, has been designed and synthesized for sensing cysteine in physiological pH. In this fluorescent probe, the coumarin was applied as the fluorophore and an allylic esters group was combined as both a fluorescence quencher and a recognition unit. The probe can selectively and sensitively detect cysteine (Cys) over homocysteine, glutathione, and other amino acids, and has a rapid response time of 30 min and a low detection limit of 47.7 nM. In addition, the probe could be applied for cell imaging with low cytotoxicity.

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“…Just introducing one acrylate group at the 7th position of coumarin endow the probe selectively sensing ability for thiols. Wei et al [31] synthesized probe 11 with simple structure (figure 11). Under single excitation wavelength at 332 nm, both Cys and Hcy shows emission wavelength at 455 nm, which is an obvious enhancement of fluorescence intensity reaching the top within 120 min.…”

Section: Coumarin-based Probes For Detecting Cysmentioning

confidence: 99%

Fluorescent probes for detecting cysteine

Yan

Sun

et al. 2018

Methods Appl. Fluoresc.

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Cysteine plays a crucial role in physiological processes. Therefore, it is necessary to develop a method for detecting cysteine. Fluorimetry has the advantages of convenient detection, short response time, high sensitivity and good selectivity. In this review, fluorescent probes that detect cysteine over the past three years are summarized based on structural features of fluorophores such as coumarin, BODIPY, rhodamine, fluorescein, CDs, QDs, etc and reaction groups including acrylate, aldehyde, halogen, 7-nitrobenzofurazan, etc. Then, effects of different combinations between fluorophores and response groups on probe properties and detection performances are discussed.

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Fluorescent coumarin-based probe for cysteine and homocysteine with live cell application

Cited by 23 publications

References 39 publications

Coumarin-Based Small-Molecule Fluorescent Chemosensors

Coumarin-Based Small-Molecule Fluorescent Chemosensors

A Fluorescent Coumarin-Based Probe for the Fast Detection of Cysteine with Live Cell Application

Fluorescent probes for detecting cysteine

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