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A kind of broad-spectrum protein fluorescent probe and its preparation method and application

A protein fluorescence and fluorescent probe technology, applied in the field of medical detection, can solve the problems of protein quantitative analysis, low sensitivity, and a small number of fluorescent probes, and achieve the effects of fast response rate, strong practical application, and easy separation and purification.

Active Publication Date: 2022-06-28
HEBEI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to provide a broad-spectrum protein fluorescent probe and its preparation method and application to solve the problem of the small number of fluorescent probes in the prior art, low sensitivity and the inability to quantitatively analyze proteins in real urine samples, etc. question

Method used

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  • A kind of broad-spectrum protein fluorescent probe and its preparation method and application
  • A kind of broad-spectrum protein fluorescent probe and its preparation method and application
  • A kind of broad-spectrum protein fluorescent probe and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1 Synthesis of PYPOS

[0050] (1) Synthesis of Compound A

[0051]

[0052]Into a 100 mL round-bottomed flask, 0.27 g (2 mmol) of 4-hydroxyphenylacetonitrile, 0.24 g (2 mmol) of 1,3-propanesultone, and 30 mL of toluene were added successively, and the stirring was turned on, heated to 110° C., and the reaction was terminated after refluxing for 8 h. . Then, the reaction solution was cooled to room temperature, and a white solid was precipitated, which was filtered off and dried to obtain compound A, which was subjected to the next reaction.

[0053] (2) Synthesis of fluorescent probe PYPOS

[0054]

[0055] 0.23 g (1 mmol) of 1-pyrenecarboxaldehyde, 0.26 g (1 mmol) of compound A, 0.17 g (2 mmol) of piperazine, and 30 mL of ethanol were successively added to a 50 mL round-bottomed flask. Turn on stirring, heat to boiling, and stop the reaction after refluxing for 8 h. After the reaction solution was cooled to room temperature and an orange solid was pre...

Embodiment 2

[0059] Example 2 AIE properties of PYPOS

[0060] The DMSO stock solution (concentration of 1 mM) of PYPOS prepared in Example 1 was added to a 2 mL EP tube, and then different volume fractions of toluene and tetrahydrofuran (V 甲苯 : V 四氢呋喃 = 0:10, 1:9, 2:8, 3:7, 4:6, 5:5, 6:4, 7:3, 8:2, 9:1, 10:0). The total volume of the solution was 1 mL, and the final concentration of PYPOS was 10 μM. The above solution was placed at room temperature for 1 h and its fluorescence spectrum (excitation wavelength 405 nm) was measured.

[0061] image 3 is the fluorescence spectrum of PYPOS in a toluene-tetrahydrofuran mixture with a toluene volume fraction of 0-100%. like image 3 As shown, tetrahydrofuran and toluene are used as benign and poor solvents for PYPOS, respectively. As the volume fraction of toluene in the toluene-tetrahydrofuran mixed solution increases, the solubility of PYPOS decreases gradually. When the volume fraction of toluene increases from 0 to 50% , the fluorescen...

Embodiment 3

[0062] Example 3 Spectral Responsiveness of PYPOS to INS

[0063] The DMSO stock solution (concentration of 1 mM) of PYPOS prepared in Example 1 was added to a 2 mL EP tube, and then deionized water, Tris-HCl buffer solution (concentration of 100 mM, pH=7) and different volumes were added to the tube in sequence. INS stock solution (concentration of 0.5mg / mL), the total solution volume is 1mL, the final concentration of PYPOS is 10μM, the final concentration of Tris-HCl buffer solution (pH=7) is 10mM, and the final concentration of INS is 0-50μg / mL, The above solution was placed at room temperature for 1 h and its fluorescence spectrum (excitation wavelength 405 nm) was measured.

[0064] Figure 4 (A) is the fluorescence spectrum of PYPOS after adding 0-50 μg / mL INS; Figure 4 (B) is the linear relationship between the fluorescence intensity of PYPOS at 540 nm and the INS concentration after adding 0-16 μg / mL INS. like Figure 4 (A) and Figure 4 As shown in (B), with th...

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Abstract

The present invention provides a broad-spectrum protein fluorescent probe and its preparation method and application. The fluorescent probe has a structure shown in formula (I), and its preparation process is as follows: (1) 4-hydroxyphenylacetonitrile and 1 , 3‑propanesultone was dissolved in toluene, heated to reflux, and after the reaction was completed, compound A was isolated; (2) compound A and 1‑pyrene formaldehyde were dissolved in ethanol and heated to reflux, and after separation and purification, the formula (Ⅰ ) fluorescent probe with the structure shown. The fluorescent probe of the invention has the advantages of simple synthesis, high sensitivity, fast and stable response, wide application range and the like. It can be used for the accurate quantification of serum albumin in urine samples, and can also be applied to clinical urine protein grading and naked-eye identification, providing a convenient and effective tool for rapid detection of proteinuria and home monitoring of patients with kidney disease.

Description

technical field [0001] The invention belongs to the technical field of medical detection, in particular to a broad-spectrum protein fluorescent probe and a preparation method and application thereof. Background technique [0002] Protein is the most basic substance that constitutes a living organism and has a complex spatial structure. There are many kinds of proteins in the human body, which constitute biomolecules with various functions, such as hormones, enzymes, antibodies, etc. Serum albumin (HSA) is a heart-shaped macromolecule composed of three domains. It is synthesized by hepatocytes and accounts for 40%-60% of plasma proteins. It is the most abundant protein in human plasma. Human plasma osmotic pressure ( 25-33mmHg) was maintained by it. HSA has important physiological functions. As a multifunctional carrier, it can reversibly bind to many biologically active molecules, participate in the transport of endogenous substances (such as fatty acids, steroids, vitami...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C309/11C07C303/22C09K11/06G01N33/68
CPCC07C309/11C09K11/06G01N33/68C09K2211/1011
Inventor 聂海亮何志霄闫宏远王振光杨春柳刘树芳
Owner HEBEI UNIVERSITY
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