Preparation and application of a water-soluble fluorescent sensor capable of ratiometric detection of cysteine

A fluorescent sensor, cysteine ​​technology, used in fluorescence/phosphorescence, instruments, luminescent materials, etc., can solve problems such as water solubility, limited application, biological toxicity, etc., achieve high selectivity, obvious selectivity, and convenient post-processing Effect

Active Publication Date: 2019-08-13
HUNAN UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In addition, many fluorescent sensors for cysteine ​​(Cys), homocysteine ​​(Hcy) and glutathione (GSH) have been prepared, but there are still several problems. First, it has been reported Many fluorescent sensors in the industry cannot distinguish these three amino acids with the reducing group sulfhydryl (-SH) well (Chen. W, et al. Anal. Chem2016, 88 (7), 3638-3646; Wang. P, et al. Sens Actuators B 2017, 245 , 297-304; Li. Y, et al. Biosens Bioelectron 2017, 90 , 117-124; Chen. Z, et al. Biosens Bioelectron 2017, 91 , 553-559; Gao. Q, et al. Anal Chem 2017, 89 (8), 4517-4524.)
followed by water solubility and biological toxicity
Although there has been a specific recognition of Cys by the combination of fluorescein isothiocyanate and acryloyl chloride (Ma. D, et al. Chem Asian J 2015, 10 (4), 894-902), but this probe must have acetonitrile (about 30% by volume) as a cosolvent, and there are also some fluorescent probes for distinguishing these three amino acids (Li. R, et al. J Mol Struct 2017, 1136 , 1-6; Ma. D, et al. Chem Asian J 2015, 10 (4), 894-902; Song. X, et al. Anal Methods 2017, 9 (12), 1891-1896; Han. C, et al. ACS Appl Mater Interfaces 2015, 7 (50), 27968-27975.), however, these probes all face a prominent defect, that is, they need to work in a mixed solvent of organic solvent and water
As we all know, the cytotoxicity of organic solvents is a big problem, and the small molecule fluorescent probe itself also has great biological toxicity, which largely limits the application in the fields of biology and medicine.

Method used

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  • Preparation and application of a water-soluble fluorescent sensor capable of ratiometric detection of cysteine
  • Preparation and application of a water-soluble fluorescent sensor capable of ratiometric detection of cysteine
  • Preparation and application of a water-soluble fluorescent sensor capable of ratiometric detection of cysteine

Examples

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Embodiment 1

[0025] Example 1: The preparation of a fluorescent sensor capable of ratiometric detection of cysteine, the specific steps are as follows:

[0026] (1) Dissolve fluorescein isothiocyanate (100 mg) and triethylamine (100 mg) in 40 mL of dichloromethane, then dissolve acryloyl chloride (231 mg) in 5 mL of dichloromethane, then Add it dropwise to the above solution, stir at room temperature for 3 h, remove most (85-95%) of dichloromethane by rotary evaporation after the reaction is completed, purify the product through a column, and dry it in vacuum to obtain product 1;

[0027] (2) Dissolve the product 1 (50 mg) synthesized in step (1) and carbon quantum dots (50 mg) prepared according to the prior art in a solution of dimethyl sulfoxide (5 mL), react at room temperature for 24 hours, and react After the end, it was first precipitated with ether, then with methanol, centrifuged, and vacuum-dried to obtain product 2.

Embodiment 2

[0028] Example 2: The preparation of a fluorescent sensor capable of ratiometric detection of cysteine, the specific steps are as follows:

[0029](1) Dissolve fluorescein isothiocyanate (100 mg) and triethylamine (100 mg) in 40 mL of dichloromethane, then dissolve acryloyl chloride (231 mg) in 5 mL of dichloromethane, then Add it dropwise to the above solution, stir at room temperature for 3 h, remove most (85-95%) of dichloromethane by rotary evaporation after the reaction is completed, purify the product through a column, and dry it in vacuum to obtain product 1;

[0030] (2) Dissolve the product 1 (250 mg) synthesized in step (1) and carbon quantum dots (50 mg) prepared according to the prior art in dimethyl sulfoxide (8 mL) solution, react at room temperature for 24 hours, and react After the end, it was first precipitated with ether, then with methanol, centrifuged, and vacuum-dried to obtain product 2.

Embodiment 3

[0031] Example 3: The preparation of a fluorescent sensor capable of ratiometric detection of cysteine, the specific steps are as follows:

[0032] (1) Dissolve fluorescein isothiocyanate (100 mg) and triethylamine (100 mg) in 40 mL of dichloromethane, then dissolve acryloyl chloride (231 mg) in 5 mL of dichloromethane, then Add it dropwise to the above solution, stir at room temperature for 3 h, remove most (85-95%) of dichloromethane by rotary evaporation after the reaction is completed, purify the product through a column, and dry it in vacuum to obtain product 1;

[0033] (2) Dissolve the product 1 (150 mg) synthesized in step (1) and carbon quantum dots (50 mg) prepared according to the prior art in dimethyl sulfoxide (10 mL) solution, react at room temperature for 24 hours, and react After the end, it was first precipitated with ether, then with methanol, centrifuged, and vacuum-dried to obtain product 2. Product 2 was then dissolved in water to a final concentration of...

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Abstract

The invention discloses preparation and application of a water-soluble fluorescence sensor for ratio checking of cysteine. The fluorescence sensor is a novel water-soluble fluorescence sensor which is prepared from a carbon quantum point, fluorescein isothiocyanate and acryloyl chloride as raw materials prepared according to the prior art and is used for implementing ratio checking of cysteine. By adopting the fluorescence sensor, high-selectivity and high-sensitivity ratio checking on cysteine can be achieved in a pure-water solution. Compared with the conventional fluorescence detection technique, the fluorescence sensor disclosed by the invention has advantages of being high in cysteine selectivity, rapid in response to cysteine, low in cytotoxicity, excellent in water dispersibility, relatively low in investment cost, simple in synthesis route and the like, is applicable to amplified synthesis and practical production application and has great application prospects in technical fields such as analytic chemistry and life sciences.

Description

technical field [0001] The invention relates to the preparation and application of a fluorescent sensor that can be used for detection, in particular to the preparation and application of a water-soluble fluorescent sensor capable of ratiometric detection of cysteine, and belongs to the field of chemical material preparation and analysis and detection. Background technique [0002] Cysteine ​​(Cys) is a very important reducing species that widely exists in biological cells. It is also one of the amino acids that must have physiological functions in the human body. It is also the reducing group thiol in more than 20 amino acids that make up proteins. One of the amino acids of (-SH), which plays an important role in maintaining the redox process of cells, and abnormal levels of biothiols can cause various diseases, such as slow growth, hair fading, edema, listlessness , liver disease, skin damage, hypoglycemia brain damage and emaciation. In addition, Cys has been widely used...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/10C09K11/06C09K11/65G01N21/64
CPCC07D493/10C09K11/06C09K11/65C09K2211/1088G01N21/6428
Inventor 陈建王宏张培盛洪永想余茂林
Owner HUNAN UNIV OF SCI & TECH
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