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Chiral fluorescent probe with spiropyran characteristics as well as preparation method and application thereof

A technique of fluorescent probe and spiropyran, which is applied in the field of fluorescent probes and achieves broad application prospects and simple synthesis.

Active Publication Date: 2019-04-05
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to their special photochromic properties, spiropyrans have been widely used in chemical and biological sensing, but there are no reports of their application in the fluorescent recognition of chiral molecules.

Method used

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  • Chiral fluorescent probe with spiropyran characteristics as well as preparation method and application thereof
  • Chiral fluorescent probe with spiropyran characteristics as well as preparation method and application thereof
  • Chiral fluorescent probe with spiropyran characteristics as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] The preparation of embodiment 1 chiral fluorescent probe

[0043] A preparation method of a chiral fluorescent probe with spiropyran characteristics, comprising the following steps:

[0044] 1-propionic acid-2,3,3-trimethylindole quaternary ammonium salt (377mg, 0.8mmol), (S)-2,2'-dihydroxy-1,1'-binaphthyl-3,3 '-Dialdehyde group (450mg, 1.32mmol) and piperidine (134mg, 1.58mmol) were added to 15mL ethanol solution, and heated to reflux for 6h. After the reaction, the product was distilled to remove the solvent, and then dichloromethane and methanol The volume ratio is 40:1 and mixed as eluent, and purified by column chromatography to obtain the target product, which is designated as probe (S)-3. 1 HNMR spectrum as figure 1 as shown, 13 C NMR spectrum as figure 2 As shown, the mass spectrum is as image 3 shown.

[0045] The preparation process of probe (R)-3 is the same as the preparation process of probe (S)-3, the only difference is that the starting material i...

Embodiment 2

[0046] Embodiment 2 Identification of chiral molecules

[0047] 1. Recognition of Phenylalanine

[0048] Dissolve the fluorescent probes (S)-3 and (R)-3 prepared in Example 1 in tetrahydrofuran solution to make the concentration 2mM, then draw 20μL into a glass test tube, add 50mM HEPES buffer to dilute to 2mL (diluted probe concentration is 2×10 -5 mol / L; H 2 O / THF=99 / 1, THF is 1%, and the system is 1% THF / HEPES system), then add 2 equivalents of zinc acetate and different equivalents of phenylalanine, measure the change of fluorescence intensity after 2h, the results are shown in Figure 4-7 . Depend on Figure 4-7 It can be seen that the chiral fluorescent probe probe (S)-3 has a large difference in fluorescence intensity for different configurations of phenylalanine, and has good enantioselectivity, with an ef value of about 9.6.

[0049]2. Recognition of leucine, valine, tryptophan and methionine

[0050] According to the above-mentioned identification method for ph...

Embodiment 3

[0052] Example 3 Cell Imaging of Phenylalanine Chiral Molecules

[0053] The fluorescent probe (S)-3 of Example 1 was applied to HeLa cells for fluorescence imaging, and the specific operation steps were as follows:

[0054] (1) The density of 3 parts is 3×10 5 cells / mL of HeLa cells at a temperature of 37°C, CO 2 Culture in an incubator with a concentration of 5% until the cells adhere to the wall;

[0055] (2) Take an aliquot of cells, add 20 μM (S)-3 and incubate for 30 min, wash the cells with PBS buffer 3 times, image under a fluorescent microscope after sample preparation, and the excitation wavelength is 445 nm;

[0056] (3) Take a portion of the cells, add 20 μM (S)-3 and incubate for 30 minutes, add D-phenylalanine and incubate for 2 hours, wash the cells with PBS buffer for 3 times, image under a fluorescent microscope after sample preparation, and the excitation wavelength is 445nm ;

[0057] (3) Take a portion of the cells, add 20 μM (S)-3 and incubate for 30 m...

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Abstract

The invention provides a chiral fluorescent probe with spiropyran characteristics as well as a preparation method and application thereof. The preparation method comprises the following steps: heating1-propionic acid-2,3,3-trimethylindole quaternary ammonium salt and (S)-2,2'-dihydroxy-1,1'-naphthalene-3,3'-dialdehyde group to react in ethanol in the presence of piperidine, and separating and purifying after the reaction is finished to obtain a product. The spiropyran chiral fluorescent probe is easy in obtaining raw materials and simple in synthesis, can not only enantioselectively identifyphenylalanine in an aqueous solution, but also can perform the fluorescence imaging for phenylalanine in cells, and has wide application prospect in the field of chiral identification.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes, and in particular relates to a chiral fluorescent probe with spiropyran characteristics, a preparation method and application thereof. Background technique [0002] Chirality is a basic attribute of nature. Important biological macromolecules involved in life activities, such as proteins, polysaccharides, enzymes, etc., all have chirality; various biological and chemical reaction processes that occur in life activities are closely related to chiral recognition and changes . Therefore, it is of great research significance to design and synthesize host molecules with enantioselective recognition and sensing properties, and to use them for rapid analysis of chiral composition of chiral compounds. Compared with other identification methods, fluorescence identification has the advantages of high sensitivity, multiple signal modes, zero background interference, real-time performance, and co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07B2200/07C07D491/107C09K11/06C09K2211/1011C09K2211/1029C09K2211/1088G01N21/6428G01N21/643
Inventor 余孝其于珊珊赵枫蒲林
Owner SICHUAN UNIV
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