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TPA-BI-based macrocyclic polyamine[12]anen 3 Compounds and their preparation and use

A TPA-BI, TAP-BI technology, applied in chemical instruments and methods, other methods of inserting foreign genetic materials, organic chemistry, etc., can solve problems such as difficulty in entering the nucleus and single function

Active Publication Date: 2020-07-17
BEIJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The current cationic liposome has a relatively single function, which can only carry out DNA condensation and transport and is difficult to enter the nucleus

Method used

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  • TPA-BI-based macrocyclic polyamine[12]anen <sub>3</sub> Compounds and their preparation and use
  • TPA-BI-based macrocyclic polyamine[12]anen <sub>3</sub> Compounds and their preparation and use
  • TPA-BI-based macrocyclic polyamine[12]anen <sub>3</sub> Compounds and their preparation and use

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0051] A TPA-BI-based macrocyclic polyamine[12]aneN 3 Compound, the structural formula (I) of described compound is as follows:

[0052]

[0053] In the formula (I), R is a macrocyclic polyamine [12]aneN 3 structural unit.

[0054] Among them, when R is , the synthesized TPA-BI-based macrocyclic polyamine [12]aneN 3 The compound is designated as 1-A, which has the following structural formula:

[0055]

[0056] when R is , the synthesized TPA-BI-based macrocyclic polyamine [12]aneN 3 The compounds are denoted as 1-B and 1-C, which have the following structural formula:

[0057]

[0058] Among them, when n=0, it is compound 1-B, and when n=1, it is compound 1-C.

[0059] The synthetic route and preparation method of compound 1-A are as follows:

[0060]

[0061]

[0062] Concrete synthetic steps include:

[0063] (1), dissolve anhydrous potassium carbonate (6g, 37.7mmol) and glycine methyl ester hydrochloride (87g, 28mmol) in the mixed solution of 60mL...

example 2

[0106] Compounds 1-A, 1-B and 1-C were configured into aqueous solutions of the same concentration (10 μM), and 0-99% tetrahydrofuran was added to the system to measure the fluorescence intensity of compounds 1A~1-C; the maximum fluorescence intensity The value is plotted against the change trend of THF addition, and obtained figure 1 A~1C, in figure 1 In A to 1C, the X-axis represents the concentration of tetrahydrofuran, and the Y-axis represents the fluorescence intensity. Depend on figure 1 It can be drawn that the macrocyclic polyamine [12]aneN based on TPA-BI of the present invention 3 The compound has a good AIE effect.

example 3

[0108] Prepare 10μM 1-A~1-C in different solvents respectively, test and plot their UV and fluorescence, and get figure 2 A~2F. It can be drawn from the figure that the macrocyclic polyamine [12]aneN based on TPA-BI of the present invention 3 The compound has the characteristics of large Stoke shift, long-wave excitation and low self-luminescence.

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PUM

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Abstract

The invention relates to a macrocyclic polyamine [12]aneN3 compound based on TPA-BI, and a preparation method and an application thereof. The compound disclosed by the invention is mainly prepared andsynthesized by means of Suzuki coupling, esterification reaction and Click reaction. The compound provided by the invention has the advantages of great Stock displacement and two-photon fluorescenceproperty as well as long wave excitation, low self-Illumination and high 3D resolution. The compound has an aggregation-inductive effect (AIE). The compound provided by the invention can form a pH stimulation responding cationic liposome with dioleoyl phosphatidylethanolamine (DOPE) to promote release of DNA in cells. The cationic liposome can enter cell nucleus efficiently so as to improve the transfection efficiency of the cells.

Description

technical field [0001] The invention relates to a non-viral gene carrier, in particular to a TPA-BI-based macrocyclic polyamine [12]aneN 3 Compounds and their preparation and use. Background technique [0002] Gene therapy is to introduce normal genes into diseased cells to replace and correct diseased genes, so as to achieve the purpose of treatment. Due to the presence of phosphate groups, the surface of nucleic acid is negatively charged. At the same time, there are many negatively charged proteins and glycolipid compounds on the cell surface, which makes it difficult for nucleic acid to enter cells directly through endocytosis. The entry into cells becomes the difficulty of gene transfection. Gene carrier becomes the key to solve this problem. [0003] Vectors are divided into two categories: viral gene carriers and non-viral gene carriers. Although viral gene vectors have high transfection efficiency, viral gene vectors also have a certain risk of carcinogenicity an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/12C07D403/14C09K11/06C12N15/87G01N21/64
CPCC07D403/12C07D403/14C09K11/06C09K2211/1007C09K2211/1014C09K2211/1044C09K2211/1059C12N15/87G01N21/6428
Inventor 卢忠林刘名轩马乐乐刘旭英
Owner BEIJING NORMAL UNIVERSITY
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