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Fluorescent probe for detecting cysteine, synthetic method of fluorescent probe and application of fluorescent probe

A cysteine ​​and fluorescent molecular probe technology, applied in the field of chemical analysis and detection, can solve the problems of unfavorable biological sample detection, small Stokes shift value, interference, etc., and achieve high sensitivity, fast response speed and high selectivity sexual effect

Inactive Publication Date: 2019-05-10
SHANGQIU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the currently developed fluorescent probe molecules for the detection of cysteine ​​have a small Stokes shift value, so the excitation light will cause interference, which is not conducive to the detection of biological samples

Method used

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  • Fluorescent probe for detecting cysteine, synthetic method of fluorescent probe and application of fluorescent probe
  • Fluorescent probe for detecting cysteine, synthetic method of fluorescent probe and application of fluorescent probe
  • Fluorescent probe for detecting cysteine, synthetic method of fluorescent probe and application of fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1: Synthesis of Fluorescent Molecular Probes

[0033] Compound 2 (80mg, 0.2mmol), triethylamine (24.0mg, 0.24mmol), 2,4-dinitrobenzenesulfonyl chloride (70.0mg, 0.24mmol), solvent methylene chloride (10mL) were reacted at room temperature 8h. After the reaction was completed, the solvent was distilled off under reduced pressure and separated by column chromatography (eluent: petroleum ether: ethyl acetate = 6:1, v / v) to obtain 110 g of product solid (yield: 87%). The product structural formula is as follows:

[0034]

[0035] 1H NMR (400MHz, DMSO) δ8.95(s, 1H), 8.25(d, J=14.7Hz, 2H), 8.06(d, J=6.8Hz, 1H), 7.89(d, J=6.7Hz, 1H ),7.77(s,1H),7.46(d,J=31.9Hz,2H),7.34–7.15(m,2H),7.16–6.96(m,2H),6.86(s,1H),3.81(s, 2H),1.60(s,2H),1.36(s,2H),0.87(s,3H).MS[ESI]:m / z,calcd for[M+H] + 635.0729, Found: 635.0737.

Embodiment 2

[0036] Example 2: Fluorescence detection of cysteine ​​by probe

[0037] The molecular probe prepared above was dissolved in a mixed buffer solution of water and dimethyl sulfoxide (H 2 O / DMSO=1 / 1, v / v, 10mM HEPES, pH 7.4)), prepared to 5μmol L -1 probe solution. Add 2 mL of prepared 5 μmol L to a 3 mL cuvette -1 Probe solution of the present invention, and then add different concentrations of cysteine ​​and mix evenly, test its fluorescence spectrum, the results are as follows image 3 shown. The fluorescence emission intensity of the solution at 530nm is plotted against the concentration of cysteine, and the concentration of cysteine ​​is 0–10 μmol L -1 In the range, there is a good linear relationship between the two ( Figure 4 ), can realize the quantitative detection of cysteine ​​in this concentration range. And this probe is not affected by some other common substances, such as Ala, Asn, Arg, Asp, Gly, Gln, Glu, Lys, Leu, Met, Phe, Pro, Trp, Tyr, Thr, Ser, His, I...

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PUM

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Abstract

The invention discloses a fluorescent probe for detecting cysteine, a synthetic method of the fluorescent probe and an application of the fluorescent probe, and belongs to the technical field of chemical analysis and detection. A benzothiazole phenothiazine fluorogen with green fluorescence emission reacts with 2, 4-dinitrobenzene sulfonyl chloride to obtain the probe which has a general structural formula as shown in the specification. The fluorogen of the probe is benzothiazole phenothiazine, and a cysteine response group is 2, 4-dinitrobenzene sulfonyl. Probe molecules have high selectivityand sensitivity to the cysteine, detection range is 0-10 micromoles*L<-1>, and detection limit is 0.12 micromole*L<-1>. The probe can be used for detecting the cysteine in water, soil and cells.

Description

technical field [0001] The invention belongs to the technical field of chemical analysis and detection, and in particular relates to a trun-on fluorescent probe for detecting cysteine, a synthesis method thereof and an application in the detection of cysteine. Background technique [0002] Cysteine ​​(Cysteien, Cys) is an important biological thiol molecule, which plays an important physiological role in the human body, such as the synthesis of related polypeptides and proteins in the body, and the combination with metal ions. Deficiency of cysteine ​​can lead to many symptoms and abnormal physiological functions, such as hair loss, slow growth, liver damage and edema. Therefore, it is very necessary to develop a highly sensitive and highly selective detection method for cysteine ​​to elucidate the physiological and pathological processes of cysteine. [0003] At present, the traditional methods for detecting cysteine ​​mainly include liquid chromatography (ZhangL.Anal.Bioa...

Claims

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Application Information

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IPC IPC(8): C07D417/04C09K11/06G01N21/64
Inventor 郝远强张银堂韦秀华马啸华瞿鹏徐茂田
Owner SHANGQIU NORMAL UNIVERSITY
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