Synthesis of fluorescence enhanced fluorescent molecular probe for detecting mercapto-containing amino acids, and application of probe

A technology of fluorescent molecular probes and mercapto amino acids, which is applied in the field of chemical analysis and detection, and achieves the effects of high sensitivity, fast response speed and stable optical properties

Inactive Publication Date: 2013-10-16
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Most of the currently reported fluorescent probes respond to cysteine ​​(Cys), homocysteine ​​(Hcy) and reduced glutathione (GSH) based on changes in fluorescence intensity, and most fluorescent probes are only Good performance outside the cell

Method used

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  • Synthesis of fluorescence enhanced fluorescent molecular probe for detecting mercapto-containing amino acids, and application of probe
  • Synthesis of fluorescence enhanced fluorescent molecular probe for detecting mercapto-containing amino acids, and application of probe
  • Synthesis of fluorescence enhanced fluorescent molecular probe for detecting mercapto-containing amino acids, and application of probe

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: 2, the preparation of 4-dinitrobenzenesulfonic acid-7-hydroxyquinoline ester

[0024]Take 7-hydroxyquinoline (145mg, 1mmol) and 2,4-dinitrobenzenesulfonyl chloride (267mg, 1mmol) and dissolve in anhydrous dichloromethane, then add triethylamine (150mg, 1.5mmol) dropwise, room temperature Under stirring for 12 hours, after the reaction ended, dichloromethane was distilled off, and dichloromethane was used as eluent to obtain 2,4-dinitrobenzenesulfonic acid 7-hydroxyquinoline ester through column chromatography, 273mg, the yield was 73%.

Embodiment 2

[0025] Embodiment 2: Preparation of molecular fluorescent probe

[0026] 7-hydroxyquinoline 2,4-dinitrobenzenesulfonate (75mg, 0.2mmol) and dimethyl sulfate (252mg, 2mmol) were dissolved in 15mL of anhydrous dichloromethane, stirred at room temperature for 5 days, a large amount of White precipitate. A white solid was obtained by suction filtration, and recrystallized from a mixed solvent of dichloromethane:methanol=1:1 (volume ratio) to obtain 30 mg of white solid fluorescent probe with a yield of 30%. 1HNMR (301MHz, DMSO): δ ppm =9.57(d, J=5.8Hz, 1H), 9.33(d, J=8.3Hz, 1H), 9.17(d, J=2.3Hz, 1H), 8.65(dd, J=8.7, 2.3Hz, 1H) , 8.60(d, J=9.1Hz, 1H), 8.45(d, J=2.1Hz, 1H), 8.40(d, J=8.7Hz, 1H), 8.24(dd, J=8.4, 5.8Hz, 1H) , 7.90(dd, J=9.0, 2.2Hz, 1H), 4.55(s, 3H), 3.36(s, 3H), 2.50(dt, J=3.6, 1.8Hz, 3H).

Embodiment 3

[0027] Example 3: Application of naked-eye and fluorescence-enhanced detection of thiol-containing amino acid fluorescent probes

[0028] The probe was dissolved in DMSO / PBS (pH=7.4) buffer solution, and the changes of its ultraviolet absorption spectrum and fluorescence spectrum were tested. Figure 1 to Figure 5 It shows that the probe has high selectivity to amino acids containing thiol in the ultraviolet spectrum and fluorescence spectrum. With the increase of the concentration of amino acid containing thiol, its ultraviolet spectrum and fluorescence spectrum change obviously, and the color of the solution changes significantly. It is suitable for At the same time, after adding mercapto amino acid, the fluorescence intensity is enhanced by 130 times, and the probe is not affected by some other amino acids, such as: cysteine ​​(Cys), aspartic acid (Asp), alanine ( Ala), Valine (Val), Phenylalanine (Phe), Histidine (His), Isoleucine (Ile), Lysine (Lys), Arginine (Arg), Proli...

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Abstract

The invention relates to a preparation method of a fluorescence enhanced fluorescent molecular probe for detecting mercapto-containing amino acids, and an application of the probe, and concretely relates to a preparation method of a 7-hydroxyquinoline derivative and an application of the 7-hydroxyquinoline derivative in the mercaptoamino acid detection. The fluorescent probe is a pure probe synthesized through directly reacting the 7-hydroxyquinoline derivative with dimethyl sulfate. The largest absorption wavelength of the molecule of the probe is 315nm; and the absorption wavelength of the probe molecule redshifts to 406nm from 315nm with the addition of the mercapto-containing amino acids, the intensity of a fluorescent spectrum at 505nm is continuously enhanced, and very strong green fluorescence is emitted. The probe molecule has the advantages of high detection sensitivity, strong identification capability on the mercapto-containing amino acids, and fast response speed, and has detection limits of Cys, GSH and Hcy mercaptoamino acids being 23nM, 52nM and 5.3nM respectively, and like probes have important application values in the biochemical field and the like.

Description

technical field [0001] The invention relates to the technical field of chemical analysis and detection, in particular to a preparation method of a fluorescent molecular probe for fluorescence-enhanced detection of mercapto-containing amino acids and its application in the detection of mercapto-containing amino acids. Background technique [0002] Cysteine ​​(Cys), homocysteine ​​(Hcy) and reduced glutathione (GSH) containing sulfhydryl groups play important roles in many physiological processes. For example, cysteine ​​(Cys) is thought to be closely associated with diseases such as Alzheimer's and Parkinson's diseases, atherosclerotic vascular disease, coronary heart disease, and renal failure. Reduced glutathione (GSH) is the main endogenous antioxidant and is regarded as an indicator of oxidative stress capacity, and the sulfhydryl content in organisms may also be affected by some oxidative stress reactions. At the same time, the use of sulfhydryl probes to identify thiol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/20G01N21/64G01N21/78
Inventor 宋相志贺伟杰韩逸飞
Owner CENT SOUTH UNIV
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