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A kind of fluorescent polylysine dendrimer, its preparation method and application

A technology of polylysine and fluorescent molecules, applied in the field of preparation of fluorescent polylysine dendrimers, can solve the problems of low contrast between tumors and normal tissues, low tumor specificity, short imaging time window, etc., and achieve Increased fluorescence lifetime and photostability, high purity, and accurate structure

Active Publication Date: 2021-07-13
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] However, the synthesis steps of these macromolecules are cumbersome, the structure is flawed, and the application in vivo is also limited by the following reasons: 1) rapid clearance by the reticuloendothelial system (RES) and renal filtration; 2) non-specific binding to normal tissues, Low tumor specificity; 3) Low contrast between tumor and normal tissue; 4) Fluorescence quenching results in a short imaging time window

Method used

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  • A kind of fluorescent polylysine dendrimer, its preparation method and application
  • A kind of fluorescent polylysine dendrimer, its preparation method and application
  • A kind of fluorescent polylysine dendrimer, its preparation method and application

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Embodiment 1

[0057] Embodiment 1: Synthesis of the first generation of fluorescent polylysine dendrimers (PDI-PLL-G1):

[0058] The molar ratio of PDI and Boc-Lys(Boc)-OPfp is 1:8.

[0059] 1.00 g of PDI was dissolved in 30 mL of DMF, and then 0.45 g of DIPEA (1.5 times the equivalent of the amino group of PDI, to absorb the acid after deprotecting the amino group in PDI) was added dropwise. 2.4 g of pentafluorophenol-activated lysine (Boc-Lys(Boc)-OPfp) was dissolved in 20 mL of dichloromethane, added to the above solution, and reacted at room temperature under nitrogen atmosphere for 24 h. The solvent was removed by rotary evaporation and dried. Column chromatography (SiO 2 , n-hexane:ethyl acetate, v:v=4:1) to separate and purify the product, and obtain the 0.5th generation fluorescent polylysine dendrimer (PDI-PLL-G0.5) after drying. Then weigh 1.00 g of PDI-PLL-G0.5, add 30 mL of dichloromethane: trifluoroacetic acid (v:v = 1:1), and stir at room temperature for 2 h. The solution ...

Embodiment 2

[0060] Embodiment 2: the synthesis of the second generation fluorescent polylysine dendrimer (PDI-PLL-G2):

[0061] The molar ratio of the amino group of PDI-PLL-G1 to Boc-Lys(Boc)-OPfp is 1:2.

[0062] 1.00 g of PDI-PLL-G1 was dissolved in 30 mL of DMF, and then 0.58 g of DIPEA was added dropwise. 3 g of Boc-Lys(Boc)-OPfp was dissolved in 20 mL of dichloromethane, added to the above solution, and reacted at room temperature under nitrogen atmosphere for 24 h. The solvent was removed by rotary evaporation and dried. Column chromatography (SiO 2 , n-hexane: ethyl acetate, v:v=4:1) the product was separated and purified to obtain the 1.5th generation fluorescent polylysine dendrimer (PDI-PLL-G1.5). Take 1.00 g of PDI-PLL-G1.5, add 30 mL of dichloromethane: trifluoroacetic acid (v:v=1:1), and stir at room temperature for 2 h. The solvent was concentrated by rotary evaporation, and the residue was added dropwise to 50 mL of glacial ether, and the precipitate was washed three t...

Embodiment 3

[0063] Embodiment 3: the synthesis of the third generation fluorescent polylysine dendrimer (PDI-PLL-G3):

[0064] The molar ratio of the amino group of PDI-PLL-G2 to Boc-Lys(Boc)-OPfp is 1:2;

[0065] 1.00 g of PDI-PLL-G2 was dissolved in 30 mL of DMF, fully dissolved, and then 0.67 g of DIPEA was added dropwise. 7.2 g of Boc-Lys(Boc)-OPfp was dissolved in 20 mL of DMF, added to the above solution, reacted at room temperature for 24 h under a nitrogen atmosphere, and concentrated by rotary evaporation. The concentrated solution was added dropwise to glacial ether (the volume ratio of the concentrated solution to glacial ether was 1:5), the precipitate was washed 3 times, and dried to obtain the 2.5th generation fluorescent polylysine dendrimer (PDI-PLL-G2.5 ). Take 1.00g of PDI-PLL-G2.5, add 30mL of trifluoroacetic acid, and stir at room temperature for 6h. After the solution was concentrated, it was added dropwise to 50 mL of glacial ether, and the precipitate was washed ...

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Abstract

The invention relates to the technical field of biological carrier materials, and discloses a fluorescent polylysine dendrimer, its preparation method and application. As the core, lysine R is connected through amide bonds, and a fluorescent polylysine dendrimer with n iterations is obtained by a divergent step-by-step method. The fluorescent macromolecule has precise structure, excellent fluorescence performance, and biocompatibility Good, long circulation time in the body, can be used for imaging analysis at the cell level and animal tissue level, targeted positioning analysis, etc., and has good application value in the field of tumor imaging diagnosis.

Description

technical field [0001] The invention relates to the technical field of biological carrier materials, in particular to a fluorescent polylysine dendrimer, its preparation method and application. Background technique [0002] Fluorescence imaging technology is widely used in the visual monitoring of biological processes due to its high selectivity and high sensitivity. An ideal fluorescent probe should have excellent fluorescence properties such as high fluorescence quantum efficiency, resistance to photobleaching, and long lifetime. At present, most commercial fluorescent imaging probes are small molecular compounds, and their development is limited by the disadvantages of poor stability, fast clearance in vivo, low specificity, few modifiable groups, and high toxicity. Dendrimers are three-dimensional macromolecules with a highly branched structure, a single molecular weight distribution, and precise and controllable structures. They are a potential carrier for imaging prob...

Claims

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Application Information

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IPC IPC(8): C08G69/40C08G83/00C09K11/06A61K49/00
CPCA61K49/0019C08G69/40C08G83/003C09K11/06C09K2211/14
Inventor 周珠贤王楷淇杨佳佳申有青
Owner ZHEJIANG UNIV
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