Application of high-specificity fluorescent probe for detecting human serum albumin

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

Active Publication Date: 2017-06-13
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 high-specificity fluorescent probe for detecting human serum albumin
  • Application of high-specificity fluorescent probe for detecting human serum albumin
  • Application of high-specificity fluorescent probe 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 to a 25 mL two-necked flask , Dissolve 0.3 mmol of acetyl chloride in 5 mL of dichloromethane, gradually drop it into the reaction flask within 30 minutes under nitrogen protection and ice bath, stir at this temperature for 1 h, and then stir 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, 149.81, 140.33, 139.45, 138.56, 137.3...

Embodiment 2

[0033] Example 2 Synthesis of 1,3-Dichloro-7-(2-thiazolylcarbonyloxy)-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 to a 25 mL two-necked flask , Dissolve 0.3 mmol of 2-thenoyl chloride in 5 mL of dichloromethane, gradually drip into the reaction flask within 30 minutes under nitrogen protection and ice bath, stir at this temperature for 1 h, and then stir 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 26.8 mg of orange solid (yield: 25.6%). 1 H NMR (400 MHz, CDCl 3 ) δ 8.02(d, J = 3.7 Hz, 1H), 7.75 – 7.69 (m, 2H), 7.66 (s, 1H), 7.39 (d, J = 2.4 Hz,1H), 7.29 (d, J = 2.4 Hz, 1H), 7.24 – 7.19 (m, 1H), 1.91 (s, 6H). 13 C NMR (100MHz, CDCl 3 ) δ 173.19, 160.01, 153....

Embodiment 3

[0035] Example 3 Synthesis of 1,3-Dichloro-7-(1-naphthylcarbonyloxy)-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 to a 25 mL two-necked flask , Dissolve 0.3 mmol of 1-naphthoyl chloride in 5 mL of dichloromethane, gradually drip into the reaction flask within 30 minutes under nitrogen protection and ice bath, stir at this temperature for 1 h, and then stir 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 33.0 mg of orange solid (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), 7.61 (t, J =7.7 Hz, 2H), 7.44 (d, J = 2.3...

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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 type of highly specific fluorescent probe for detecting human serum albumin, which belongs to the field of fine chemicals. Background technique [0002] Human serum albumin (HSA) is a cyclic protein in the human body that relies on 17 disulfide bonds to link 585 amino acids, with a molecular weight of 66 kDa. HSA is only synthesized in the liver, and the synthesis rate of normal human HSA is 12-25 g / d. HSA is secreted into plasma and tissue fluid soon after synthesis. It is the most abundant protein in plasma. Its content in plasma of healthy people is 35-50 g / L, which accounts for more than half of the total plasma protein. The content of HSA in human plasma is affected by nutrition and health status, and is one of the important indicators of routine blood examination. [0003] HSA participates in a variety of physiological and pathological processes in the human body, including: maintaining plasma colloidal os...

Claims

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Application Information

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IPC IPC(8): G01N21/64C07D219/06
CPCC07D219/06G01N21/6486
Inventor 崔京南冯磊王铮
Owner 王铮
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