A Ratiometric Fluorescent Probe for Cysteine and Homocysteine Displaying a Large Emission Shift

Lin, Weiying; Long, Lingliang; Yuan, Lin; Cao, Zengmei; Chen, Bingbing; Tan, Wen

doi:10.1021/ol802436j

Cited by 302 publications

(116 citation statements)

References 21 publications

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“…In recent decades, many studies have demonstrated that metabolic disorder of biothiols will lead to extreme damage in human and numerous other animals (Townsend et al, 2003;Reddie and Carroll, 2008;Weerapana et al, 2010). Specifically, a low level of biothiols in vivo may cause slowed growth, liver damage, weight loss, and some other adverse influences (Wang et al, 2005;Duan et al, 2008;Yang et al, 2012), while a high level of biothiols is closely related to Parkinson's, Alzheimer's, and cardiovascular diseases (Heafield et al, 1990;Rusin et al, 2004;Lin et al, 2008;Yang et al, 2011). Thus, a lot of effort has been put into quantifying the lowmolecule-weight biothiols in serum (Ni et al, 2015;Ghasemi et al, 2015).…”

Section: Introductionmentioning

confidence: 99%

Detection of biological thiols based on a colorimetric method

Sun

Zhang

et al. 2016

J. Zhejiang Univ. Sci. B

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Abstract:Biological thiols (biothiols), an important kind of functional biomolecules, such as cysteine (Cys) and glutathione (GSH), play vital roles in maintaining the stability of the intracellular environment. In past decades, studies have demonstrated that metabolic disorder of biothiols is related to many serious disease processes and will lead to extreme damage in human and numerous animals. We carried out a series of experiments to detect biothiols in biosamples, including bovine plasma and cell lysates of seven different cell lines based on a simple colorimetric method. In a typical test, the color of the test solution could gradually change from blue to colorless after the addition of biothiols. Based on the color change displayed, experimental results reveal that the percentage of biothiols in the embryonic fibroblast cell line is significantly higher than those in the other six cell lines, which provides the basis for the following biothiols-related study.

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Section: Introductionmentioning

confidence: 99%

Detection of biological thiols based on a colorimetric method

Sun

Zhang

et al. 2016

J. Zhejiang Univ. Sci. B

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“…Once the quinone is formed, even at low concentrations, it may add up a nucleophilic -SH compound relatively easily. Rusin et al 34 showed that when cysteine or homocysteine reacts with the carbonyl moieties of xanthene dyes, absorptiometric or fluorometric maxima are red-shifted as a result of -SH addition reactions, arising from intramolecular charge transfer (ICT) between electron-rich and electrondeficient groups 35 within the adduct molecule. In the case when phenols are oxidized faster than thiols, the Michael addition of nucleophilic thiols to quinones (i.e.…”

Section: Resultsmentioning

confidence: 99%

A Novel Spectrofluorometric Probe for the Determination of Peroxynitrite Anion Scavenging Activity of Biothiols and Amino Acids

et al. 2016

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In this study, a novel fluorometric method for the determination of peroxynitrite anion (ONOO -) scavenging (PAS) activity of amino acids and biothiols, which can mostly trap peroxynitrite in vivo, is described. This assay is based on the conversion of a gentisic acid probe to its non-fluorescent oxidation products with ONOO -. The attenuation of the fluorescence intensity (FI) of the probe upon peroxynitrite attack is diminished with antioxidants, the difference in FI being related to the PAS activity of the antioxidants. The IC50 (50% inhibitive concentration) values of biothiols, amino acids and tissue homogenates were estimated, in comparison with the reference Pyrogallol Red (PR) bleaching method. PR is the most suitable and frequently used dye to determine PAS activity, but is relatively insensitive. The developed fluorometric assay is highly sensitive to allow determinations of the PAS activity of amino acids.

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“…As a result, fluorescent sensors have become a hot topic in the detection of different metal ions (14)(15)(16), cations (17), anions (18)(19)(20), and biomolecules (21)(22)(23). To date, the use of fluorescent sensors for the detection of biomolecules (24) has received much attention and the development of sensitive and specific probes for thiols is of critical importance for understanding their roles in disease.…”

Section: Introductionmentioning

confidence: 99%

Rhodol‐based far‐red fluorescent probe for the detection of cysteine and homocysteine over glutathione

et al. 2016

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The simultaneous discrimination of cysteine (Cys), homocysteine (Hcy) and glutathione (GSH) is of great importance due to their roles in biology and close link to many diseases, especially via the development of a far-red fluorescent probe that could be used for rapid, selective, and sensitive detection of all three. Herein, we report the characterization of a far-red fluorescent probe with turn-on fluorescence properties and visible color changes that could be used for the detection of cysteine and homocysteine over glutathione. In this study we found that the sensor could discriminate cysteine and homocysteine over glutathione within 20 min. Function of this probe was based on the conjugate addition-cyclization reaction and showed a low detection limit to cysteine and homocysteine. Upon the addition of cysteine and homocysteine, the absorption band at 592 nm rose gradually and fluorescence was detected at 645 nm. The color changed from colorless to blue and fluorescence changed from absent to strong red fluorescence, which could be differentiated by the naked eye. All these unique features make this probe particularly potentially favorable for use in cysteine/homocysteine sensing and bioimaging applications. Copyright © 2016 John Wiley & Sons, Ltd.

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A Ratiometric Fluorescent Probe for Cysteine and Homocysteine Displaying a Large Emission Shift

Cited by 302 publications

References 21 publications

Detection of biological thiols based on a colorimetric method

Detection of biological thiols based on a colorimetric method

A Novel Spectrofluorometric Probe for the Determination of Peroxynitrite Anion Scavenging Activity of Biothiols and Amino Acids

Rhodol‐based far‐red fluorescent probe for the detection of cysteine and homocysteine over glutathione

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