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Branch-shaped organic fluorescent dye biological probe and preparation method thereof

A fluorescent dye and biological probe technology, applied in the field of dendritic organic fluorescent dye biological probes and preparation, can solve problems such as fluorescence background interference, increase the labeling sensitivity, reduce the probability of mutual collision and quenching, and achieve high sensitivity. Effect

Active Publication Date: 2010-03-03
TIANJIN URBAN CONSTR COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, except for cyanine dyes, other dyes themselves will produce strong fluorescence background interference

Method used

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  • Branch-shaped organic fluorescent dye biological probe and preparation method thereof
  • Branch-shaped organic fluorescent dye biological probe and preparation method thereof

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preparation example Construction

[0018] The preparation method of dendritic organic fluorescent dye biological probe of the present invention comprises the following steps:

[0019] 1) Preparation of dendritic organic fluorescent dyes

[0020] ①Put 2,2-dimethoxyethylamine and methyl acrylate with a molar ratio of 1:3 in a methanol solvent, stir evenly, and react for two days at a temperature of 35-50°C. Analysis and separation, to obtain methyl ester compound 1;

[0021] ② Dissolve the above-mentioned methyl ester compound 1 and ethylenediamine with a molar ratio of 1:3 in methanol solvent, put them in a reaction bottle and stir, under the protection of nitrogen, react in the dark for 2 to 3 days, and remove the excess by suction with an oil pump. Ethylenediamine, to obtain a generation of dendrimer 2. The product is directly used in the next step reaction;

[0022] ③ take the above-mentioned first-generation dendritic compound 2 and fluorescent dye with a molar ratio of 1:2, dissolve them in methanol solv...

Embodiment 1

[0031] Example 1: Preparation of folic acid-chitosan oligosaccharide-dendritic organic fluorescent dye biological probe No. 1.

[0032] 1. Preparation of Dendritic Organic Fluorescent Dye

[0033] (1) Put 3g (28.6mmol) of 2,2-dimethoxyethylamine and 30ml of methanol in a 50ml round bottom flask, stir evenly, add 9.8g of methyl acrylate, and react at a temperature of 50°C for 48h, The reaction was stopped, and the solvent was removed with a vacuum rotary evaporator, and the residue was separated by column chromatography to obtain methyl ester compound 1.

[0034] (2) Dissolve 1.0g of methyl ester compound 1 in 15mL of methanol, add 1.5g of ethylenediamine, stir in a 50mL reaction bottle, and react in the dark for 3 days under nitrogen protection, and remove excess ethylenediamine by suction with an oil pump , to obtain a first-generation dendrimer 2. The product was directly used in the next reaction.

[0035] (3) Take 65.5 mg of compound 2 and 20 mg of carboxyl TO, dissolve...

Embodiment 2

[0042] Example 2: Preparation of folic acid-chitosan oligosaccharide-dendritic organic fluorescent dye biological probe No. II.

[0043] Change Example 1 step 1 to:

[0044] 1. Preparation of Dendritic Organic Fluorescent Dye

[0045] (1) Put 3g (28.6mmol) of 2,2-dimethoxyethylamine and 30ml of methanol in a 50ml round bottom flask, stir evenly, add 9.8g of methyl acrylate, and react at a temperature of 50°C for 48h, The reaction was stopped, and the solvent was removed with a vacuum rotary evaporator, and the residue was separated by column chromatography to obtain methyl ester compound 1.

[0046] (2) Dissolve 1.0g of methyl ester compound 1 in 15mL of methanol, add 1.5g of ethylenediamine, stir in a 50mL reaction bottle, and react in the dark for 3 days under nitrogen protection, and remove excess ethylenediamine by suction with an oil pump , to obtain a first-generation dendrimer 2. The product was directly used in the next reaction.

[0047] (3) Take 33.3mg of the fir...

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Abstract

The invention provides a branch-shaped organic fluorescent dye biological probe. The biological probe structure comprises a probe which is formed by that one to fifteen branch-shaped organic fluorescent dye molecules are connected on one chitosan oligosaccharide molecule and are then combined with one folacin molecule. The invention provides a method for preparing the branch-shaped organic fluorescent dye biological probe simultaneously. The probe and the method have the effects that the preparation method of the biological probe is simple, has better marking targeting performance on the variant cells and provides convenience for the research on the structure-activity relationship of the marked variant cell. During the marking process, the obvious fluorescent adduction effect is presented, the biocompatibility of the biological probe and the cell is increased, the optical stability is improved obviously, and the marking sensitiveness is increased. The biological probe has low toxicityon the detected article, and has high sensitiveness and little using amount. The biological probe has the advantages of wide spectrum range, large molar extinction coefficient, having no fluorescent background and high yield.

Description

technical field [0001] The invention relates to the cross field of chemistry and biotechnology, in particular to a dendritic organic fluorescent dye biological probe and a preparation method. Background technique [0002] As we all know, cancer has become the number one killer that threatens human health, and how to effectively control its occurrence and development has become a top priority. Most scholars believe that in the prevention and treatment of tumors, secondary prevention of tumors, that is, early detection, early diagnosis, and early treatment will be the direction for greatly improving the curative effect of solid tumors for a long period of time in the future. Molecular biomarkers have attracted more and more attention in medical early diagnosis due to their advantages of cheapness, safety and accuracy. At present, this technology has been well applied in the identification of cancer and AIDS. [0003] Compared with traditional isotope detection, the relevant ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06
Inventor 费学宁兰云泉张宝莲谷迎春
Owner TIANJIN URBAN CONSTR COLLEGE