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Application of a Class of Highly Specific Fluorescent Probes for Detecting Human Serum Albumin

A serum albumin and fluorescent probe technology, applied in the field of fine chemicals, can solve the problems of high cost, interference, complicated and time-consuming operation, etc., and achieve the effects of high sensitivity, rapid and sensitive detection, and simple and easy synthesis process.

Active Publication Date: 2019-12-27
王铮
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the dye binding method and size exclusion chromatography are relatively simple to operate and low in cost, they have poor specificity and are easily interfered by other substances in biological samples.
Although immunochemistry and mass spectrometry-based quantitative methods have good specificity, the operation is complex, time-consuming and costly, requiring specific reagents and instruments

Method used

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  • Application of a Class of Highly Specific Fluorescent Probes for Detecting Human Serum Albumin
  • Application of a Class of Highly Specific Fluorescent Probes for Detecting Human Serum Albumin
  • Application of a Class of Highly Specific Fluorescent Probes for Detecting Human Serum Albumin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1 Synthesis of 1,3-dichloro-7-acetoxy-9,9-dimethyl-2(9H)-acridone (DDAA)

[0032] Add 0.25 mmol of 1,3-dichloro-7-hydroxy-9,9-dimethyl-2(9H)-acridone, 0.31 mmol of triethylamine and 10 mL of dichloromethane into a 25 mL two-necked bottle , 0.3 mmol of acetyl chloride was dissolved in 5 mL of dichloromethane, under the conditions of nitrogen protection and ice bath, gradually drop into the reaction bottle within 30 min, stirred at this temperature for 1 h, and then stirred overnight at room temperature. The solvent was removed by rotary evaporation under reduced pressure, and the remaining solid was purified by column chromatography. The developing solvent was ethyl acetate:petroleum ether=1:5 (v:v) to obtain 45.9 mg of orange solid (yield 52.5%). 1 H NMR (400 MHz, CDCl 3 ) δ 7.66 (d, J = 8.5 Hz, 1H), 7.63 (s, 1H), 7.24 (d, J = 2.3 Hz, 1H), 7.13 (dd, J = 8.5, 2.3Hz, 1H), 2.34 (s, 3H), 1.88 (s, 6H). 13 C NMR (100 MHz, CDCl 3 ) δ 173.16,168.81, 153.32, 149....

Embodiment 2

[0033] Example 2 Synthesis of 1,3-dichloro-7-(2-thiazolylformyloxy)-9,9-dimethyl-2(9H)-acridone (DDAT)

[0034]Add 0.25 mmol of 1,3-dichloro-7-hydroxy-9,9-dimethyl-2(9H)-acridone, 0.31 mmol of triethylamine and 10 mL of dichloromethane into a 25 mL two-necked bottle , 0.3 mmol of 2-thiophenoyl chloride was dissolved in 5 mL of dichloromethane, under the condition of nitrogen protection and ice bath, gradually drop into the reaction bottle within 30 min, stirred at this temperature for 1 h, and then stirred overnight at room temperature . The solvent was removed by rotary evaporation under reduced pressure, and the remaining solid was purified by column chromatography. The developing solvent was ethyl acetate:petroleum ether = 1:5 (v:v), and 26.8 mg of orange solid was obtained (yield 25.6%). 1 H NMR (400 MHz, CDCl 3 ) δ8.02 (d, J = 3.7 Hz, 1H), 7.75 – 7.69 (m, 2H), 7.66 (s, 1H), 7.39 (d, J = 2.4Hz, 1H), 7.29 (d, J = 2.4 Hz, 1H), 7.24 – 7.19 (m, 1H), 1.91 (s, 6H). 13 C...

Embodiment 3

[0035] Example 3 Synthesis of 1,3-dichloro-7-(1-naphthylformyloxy)-9,9-dimethyl-2(9H)-acridone (DDAN)

[0036] Add 0.25 mmol of 1,3-dichloro-7-hydroxy-9,9-dimethyl-2(9H)-acridone, 0.31 mmol of triethylamine and 10 mL of dichloromethane into a 25 mL two-necked bottle , 0.3 mmol of 1-naphthoyl chloride was dissolved in 5 mL of dichloromethane, under the condition of nitrogen protection and ice bath, gradually drop into the reaction bottle within 30 min, stirred at this temperature for 1 h, and then stirred overnight at room temperature . The solvent was removed by rotary evaporation under reduced pressure, and the remaining solid was purified by column chromatography. The developing solvent was ethyl acetate:petroleum ether = 1:5 (v:v), and 33.0 mg of orange solid was obtained (yield 28.6%). 1 H NMR (400 MHz, CDCl 3 ) δ 9.04(d, J = 8.7 Hz, 1H), 8.52 (d, J = 7.3 Hz, 1H), 8.16 (d, J = 8.1 Hz, 1H), 7.96(d, J = 8.2 Hz, 1H), 7.77 (d, J = 8.5 Hz, 1H), 7.73 – 7.65 (m, 2H), ...

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Abstract

The invention relates to application of a high-specificity fluorescent probe for detecting human serum albumin, and belongs to the field of fine chemical engineering. The high-specificity fluorescent probe is a 1,3-dichloro-7-hydroxyl-9,9-dimethyl-2(9H)-acridone compound ester derivative, and is used for detecting the existence of HAS (human serum albumin) in different biological samples and the quantitative measuring of activity. The enzyme activity measuring process specifically comprises the following steps of selecting hydrolysis reaction of the 1,3-dichloro-7-hydroxyl-9,9-dimethyl-2(9H)-acridone compound ester derivative as probe reaction, and selecting proper primer concentration to detect the generation amount of a hydrolyzing metabolite (1,3-dichloro-7-hydroxyl-9,9-dimethyl-2(9H)-acridone) in unit time within the online reaction zones, so as to measure the actual activity of the HAS in each biological sample. The high-specificity fluorescent probe can be used for quantitatively evaluating the activity of the HAS in different biological samples.

Description

technical field [0001] The invention relates to the application of a class of highly specific fluorescent probes for detecting human serum albumin, which belongs to the field of fine chemical industry. Background technique [0002] Human serum albumin (human serum albumin, HSA) is a circular protein in the human body that relies on 17 disulfide bonds to connect 585 amino acids, with a molecular weight of 66 kDa. HSA is only synthesized in the liver, and the normal human HSA synthesis rate is 12-25 g / d. HSA is secreted into plasma and interstitial fluid soon after synthesis. It is the most abundant protein in plasma. Its content in healthy human plasma is 35-50 g / L, accounting for more than half of the total protein in plasma. HSA content in human plasma is affected by nutrition and health status, and is one of the important indicators of blood routine examination. [0003] HSA participates in a variety of physiological and pathological processes in the human body, includin...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): G01N21/64C07D219/06
CPCC07D219/06G01N21/6486
Inventor 崔京南冯磊王铮
Owner 王铮
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