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Preparation method and use of mercapto-containing amino acid fluorescent probe

A technology of fluorescent probes and probe molecules, which is applied in the field of chemical analysis and detection, can solve problems such as poor water solubility, and achieve low cost, good selectivity, and simple synthesis

Active Publication Date: 2016-07-27
SUZHOU ROWLAND BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of these fluorescent probes have poor water solubility, and can only monitor cysteine, homocysteine ​​and glutathione in organic solvents or mixed solvents of organic solvents and water, so that they can be used in biological The application in samples or in vivo is limited, so it is of great significance to develop fluorescent probes with higher aqueous solution

Method used

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  • Preparation method and use of mercapto-containing amino acid fluorescent probe
  • Preparation method and use of mercapto-containing amino acid fluorescent probe
  • Preparation method and use of mercapto-containing amino acid fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1: the synthesis of compound 1

[0023] 3-Nitrophthalic anhydride (1.9361g, 10mmol) was dissolved in 20ml of acetic acid, n-butylamine (1.0951g, 15mmol) was slowly added, stirred at room temperature for 10min, heated up, and refluxed at 120°C for 2.5h. After the reaction, cool to room temperature, pour the reaction solution into 50ml of cold water, and after the solid is completely precipitated, filter under reduced pressure, and wash the filter cake with cold water three times (9ml×3) to obtain compound 1 as a white solid. Yield: 2.1252 g. Yield: 85.7%. Compound 1 was characterized as follows: 1HNMR (500MHz, DMSO): δH8.27(d, J=8.1Hz, 1H), 8.16(d, J=7.5Hz, 1H), 8.05(t, J=7.8Hz, 1H), 3.57(t, J=7.1Hz, 2H), 1.55–1.61(m, 2H), 1.39–1.20(m, 2H), 0.90(t, J=7.4Hz, 3H).13CNMR(126MHz, DMSO)δC: 166.51, 163.86, 144.63, 136.54, 134.05, 128.62, 127.17, 123.50, 38.13, 30.24, 19.94, 13.94.

Embodiment 2

[0024] Embodiment 2: the synthesis of compound 2

[0025]Compound 1 (0.4964g, 2mmol) obtained in the previous step was dissolved in 15ml of methanol, 10% w / w Pd / C (0.0496g, 5mol%) was added, the system was vacuumed, hydrogen was introduced and stirred, and refluxed at 65°C for 12h. After the reaction was terminated, the solid catalyst was removed by suction filtration under reduced pressure, the obtained filtrate was rotary evaporated under reduced pressure to remove the solvent, and compound 2 was obtained by separation by chromatography column. Yield: 0.6240 g. Yield: 71.5%. Compound 2 was characterized as follows: 1HNMR (500MHz, CDCl3) δ7.42 (dd, J = 8.3, 7.1Hz, 1H), 7.16 (d, J = 7.6Hz, 1H), 6.86 (d, J = 8.8Hz, 1H) ,5.13(s,1H),3.65(t,J=7.3Hz,2H),1.63–1.70(m,2H),1.35–1.42(m,2H).0.95(t,J=7.4Hz,3H). 13CNMR (126MHz, DMSO) δC: 170.38, 168.77, 145.15, 135.02, 132.86, 120.96, 112.58, 111.38, 37.37, 30.76, 20.09, 13.69.

Embodiment 3

[0026] Embodiment 3: the synthesis of compound 3

[0027] Compound 2 obtained in the previous step was dissolved in 10 ml of 50% sulfuric acid, stirred under an ice-water bath at 0°C, and aqueous sodium nitrite solution (0.0692 mg, 1 mmol, 2 mL of water) was slowly added dropwise. After continuing to stir at 0°C for 30min, the mixture was heated to 90°C and the reaction was continued for 1h. After the reaction, pour the reaction solution into 50ml of water, extract 3 times with ethyl acetate (20mL×3), wash with saturated brine, dry over anhydrous sodium sulfate, remove the solvent by rotary evaporation, and separate by column chromatography after vacuum drying Compound 3. Yield: 0.1862 g. Yield: 85.4%. Compound 3 was characterized as follows: 1HNMR (500MHz, CDCl3) δ7.70(s, 1H), 7.56(t, J=7.6Hz, 1H), 7.36(d, J=7.2Hz, 1H), 7.15(d, J= 8.4Hz, 1H), 3.65(t, J=7.3Hz, 2H), 1.68–1.62(m, 2H), 1.40–1.32(m, 2H), 0.95(t, J=7.4Hz, 3H).13CNMR( 126MHz, DMSO) δC: 170.51, 167.91, 154.60, 1...

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Abstract

The invention discloses a novel compound for cysteine, homocysteine and glutathione fluorescent recognition, relates to a preparation method and a use of a novel fluorescent probe and belongs to the technical field of chemical analysis detection. The novel fluorescent probe has a molecular structural formula shown in the description. The novel fluorescent probe is used for fluorescent sensing analysis of cysteine, homocysteine and glutathione in the environment or a biological sample, has good selectivity and good interference resistance, can sensitively and fast distinguish a mercapto-containing amino acid in a plurality of amino acids and has a good application prospect.

Description

technical field [0001] The present invention relates to the technical field of chemical analysis and detection, in particular to a preparation method of a novel sulfhydryl-containing amino acid fluorescent probe and the performance of the fluorescent probe in detecting cysteine, homocysteine ​​and glutathione application. Background technique [0002] Biothiols are closely related to the life activities of organisms. Cysteine ​​(Cys) is a common amino acid in the human body. It participates in the metabolic process of the human body and has powerful physiological functions. Homocysteine ​​(Hcy) is an amino acid with little difference from cysteine, which is converted from the important amino acid methionine in the body. Medical research shows that their content changes in organisms can be used as the basis for diagnosing diseases, such as renal failure, Alzheimer's disease, Parkinson's disease, cardiovascular disease, coronary heart disease, etc. In addition, glutathione ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D209/48G01N21/64
Inventor 宋相志高丽刘兴江
Owner SUZHOU ROWLAND BIOTECH
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