Cholic acid modified amphiphilic pyrene derivative fluorescent probe as well as synthesis method and application thereof

A technology of fluorescent probes and pyrene derivatives, which is applied in the field of protein detection, can solve the problems of low sensitivity, strong hydrophobicity, limited application of biological detection object sensing, etc., and achieves the effects of low equipment requirements and simple operation.

Inactive Publication Date: 2016-10-26
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0004] However, the existing fluorescent probe molecules for protein detection are highly dependent on molecular synthesis technology and molecular selectivity, and most of them are highly hydrophobic, which limits their application in aqueous solutions and sensing of biological detection objects.
Moreover, some fluorescent chemical sensors have shortcomings such as long detection time and low sensitivity.
Amphiphilic cholic acid molecules have good biocompatibility, chemical stability, and amphiphilic structure, so they can form specific non-covalent supramolecular aggregates in water, and use fluorescent sensors of cholic acid derivative aggregates to detect proteins detection of

Method used

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  • Cholic acid modified amphiphilic pyrene derivative fluorescent probe as well as synthesis method and application thereof
  • Cholic acid modified amphiphilic pyrene derivative fluorescent probe as well as synthesis method and application thereof
  • Cholic acid modified amphiphilic pyrene derivative fluorescent probe as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] A fluorescent probe based on cholic acid-modified amphiphilic pyrene derivatives was synthesized with the following structural formula:

[0061]

[0062] Its synthetic method comprises the following steps:

[0063] 1) Synthesis of pyrenesulfonyl derivatives

[0064] Under the conditions of nitrogen protection and ice-bath stirring at a flow rate of 0.6-0.8mL / s, 1.47mL (9.97mmol) of 1,8-diamino-3,6-diox octane, and then 0.30 g (0.997 mmol) of pyrenesulfonyl chloride was dissolved in 40 mL of chloroform and added dropwise to the above solution. After the dropwise addition, stir at room temperature for 2 hours. After stopping the reaction, wash the reaction solution with saturated brine for 6 to 7 times, then dry it with anhydrous sodium sulfate overnight, distill off chloroform, and use dichloromethane and methanol at a volume ratio of The mixed solvent of 30:1 is used as eluent column chromatography purification product, obtains the pyrenesulfonyl derivative shown i...

Embodiment 2

[0074] A fluorescent probe based on cholic acid-modified amphiphilic pyrene derivatives was synthesized with the following structural formula:

[0075]

[0076] Its synthetic method step is as follows:

[0077] In step 1 of the synthesis of pyrenesulfonyl derivatives in Example 1, the 1,8-diamino-3,6-dioxoctane used was replaced with 3,6,9-trioxaundecane with an equimolar mass - 1,11-diamine replacement, other steps are the same as the corresponding Example 1.

Embodiment 3

[0079] A fluorescent probe based on cholic acid-modified amphiphilic pyrene derivatives was synthesized with the following structural formula:

[0080]

[0081] In step 1 of the synthesis of pyrenesulfonyl derivatives in Example 1, the 1,8-diamino-3,6-dioxoctane used was mixed with 3,6,9,12-tetraoxadecane of equimolar mass Hexane-1,16-diamine was replaced, and other steps were the same as the corresponding Example 1.

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Abstract

The invention discloses a cholic acid modified amphiphilic pyrene derivative fluorescent probe as well as a synthesis method and application thereof and belongs to the technical field of protein detection. The fluorescent probe has the advantages of good chemical stability, good biocompatibility, high response speed, high sensitivity, wide response range, low detection limit and the like, and can be used for determining protein in time in an online manner. The fluorescent probe can be used for selectively detecting bovine serum albumin (BSA) and human serum albumin (HAS) in non-metal protein and the detection limits can reach 19.8nmol / L (1.32Mug / mL) and 24.5nmol / L (1.64Mug / mL).

Description

technical field [0001] The invention belongs to the technical field of protein detection, and relates to a fluorescent probe for measuring protein in aqueous phase and its synthesis method and detection method, in particular to a fluorescent probe based on cholic acid-modified amphiphilic pyrene derivatives and its synthesis methods and applications. Background technique [0002] Protein is an important biological macromolecule in the living body, the material basis of life activities, and the basic material that constitutes all tissues in the living body. Every cell and all important components in the body have protein participation, so it is compatible with various forms life activities are closely linked. At the same time, problems such as protein post-translational modification, protein-protein interaction, and protein conformation still depend on protein research. Therefore, the research on protein-specific recognition and quantitative analysis methods will directly p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07J41/00G01N21/64
CPCC07J41/0055C09K11/06C09K2211/10C09K2211/1011G01N21/6486
Inventor 丁立平范俊梅郑德民卜雨崔华华房喻
Owner SHAANXI NORMAL UNIV
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