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Organic fluorochrome molecule and synthesis method and application thereof

A technology of fluorescent dyes and synthesis methods, applied in the field of organic fluorescent dye molecules and their synthesis, and nanoparticles used in the fluorescent dye field of living cells, can solve the problems of poor modifiability, high price, few types, etc., and achieves good stability, The effect of cheap raw materials and convenient preparation

Inactive Publication Date: 2014-05-07
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the current fluorescent dyes (such as PI, DAPI, Hoechst33342, etc.) that can specifically localize to cells have many problems, such as: few types, expensive, poor modifiability, etc.

Method used

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  • Organic fluorochrome molecule and synthesis method and application thereof
  • Organic fluorochrome molecule and synthesis method and application thereof
  • Organic fluorochrome molecule and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] The synthetic route is as follows:

[0045]

[0046] In the formula: Me is methyl.

[0047] 1) Add 57g of raw material (2',3"-dibromo-1,2,7,8-tetrahydro-2",3'-dimethoxy-3,4:5,6 into a 2500ml round bottom flask -Dibenzophenanthrene-9,10-dicarboxylic acid anhydride) and 59g n-dodecylamine, and add 100ml DMF, react at 70℃ for 24 hours, then spin dry the reaction solution and wash with dichloromethane , Obtain 42.6g lactimide product, yield 70%;

[0048] 2) Take 740 mg of the lactimide product obtained in step 1), 384 mg of 2-thiophene boronic acid and 424 mg of Na 2 CO 3 Add to a 25ml two-neck flask, add 50ml of toluene, 30ml of ethanol and 20ml of aqueous solution with a syringe under the protection of argon. After 5 minutes of argon, add 50mg of the catalyst tetrakis(triphenylphosphine) palladium. The heating reaction is carried out under the heating temperature of 90~110℃, and the reaction is 12 hours. After the reaction is completed, the organic layer is taken and MgSO 4 Dr...

Embodiment 2

[0060] The synthetic route is as follows:

[0061]

[0062] In the formula: Me is methyl.

[0063] 1) Add 57g of raw material (2',3"-dibromo-1,2,7,8-tetrahydro-2",3'-dimethoxy-3,4:5,6 into a 2500ml round bottom flask -Dibenzophenanthrene-9,10-dicarboxylic acid anhydride) and 59g n-dodecylamine, and add 100ml DMF, react at 70℃ for 24 hours, then spin dry the reaction solution and wash with dichloromethane , Obtain 42.6g lactimide product, yield 70%;

[0064] 2) Take 740 mg of the lactimide product obtained in step 1), 1130 mg of 5-diphenylamino-2-thiophene boronic acid and 424 mg of Na 2 CO 3 Add to a 25ml two-neck flask, add 5ml of toluene, 3ml of ethanol and 2ml of aqueous solution with a syringe under argon protection, add 50mg of catalyst tetrakis(triphenylphosphine) palladium after 5 minutes of argon protection, under argon protection Reflux the reaction for 12 hours, after the completion of the reaction, take the organic layer and use MgSO 4 Dry, filter, spin-dry, and separate...

Embodiment 3

[0077] The aqueous solution of nanoparticles containing 2-thienyl-substituted organic fluorescent dye molecules of Example 1 and the aqueous solution of nanoparticles containing 5-diphenylamino-2-thienyl-substituted organic fluorescent dye molecules of Example 2 were performed Ultraviolet-visible absorption spectroscopy and fluorescence spectroscopy were measured, and the optical property data are shown in Table 1.

[0078] Table 1.

[0079]

[0080] Note: The quantum yield is the absolute quantum yield in aqueous solution.

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Abstract

The invention belongs to the field of cell fluorescence imaging, and relates to an organic fluorochrome molecule and a synthesis method and application thereof. The synthesis method comprises the following steps of carrying out heating reaction on 2',3'-dibromo-1,2,7,8-tetrahydro-2',3'-dimethoxy-3,4:5,6-dibenzophenanthrene-9,10-dicarboxylic anhydride and dodecylamine in organic solvent, reacting the obtained lactim with aroma boric acid and Na2CO3 in organic solvent under argon shield in the presence of four (triphenylphosphine) palladium so as to obtain the organic fluorochrome molecule shown as formula (I). The organic fluorochrome molecule is prepared into nano particles to be used as fluorochrome of living cells and used in fluorescence imaging of living cells. The synthesis method for the organic fluorochrome molecule and the nano particles thereof is simple, uses cheap raw materials, has good stability, and is convenient for preparing in large scale. (img file='DDA0000453547680000011.TIF' wi='808' he='434' / ).

Description

Technical field [0001] The present invention belongs to the field of cell fluorescence imaging, and relates to a class of organic fluorescent dye molecules with multicolor fluorescence and a method for synthesizing the same, and nanoparticles obtained from the organic fluorescent dye molecules are used as fluorescent dyes for living cells and are used in living cells. Application in fluorescence imaging. Background technique [0002] As an important unit of life, cells play an important role in the growth of living organisms. For example, the genetic material contained in cells plays a vital role in gene expression, replication, recombination, and repair. The changes in the tissue structure of cells are closely related to the phenotype of the disease. For example, the relationship between nuclear modified cations and cancerous transformation of tumor cells has been discovered by scientists (D. Zink, A.H. Fischer, J.A. Nickerson, Nat. Rev. Cancer 2004, 4,677). Therefore, the stu...

Claims

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Application Information

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IPC IPC(8): C09B57/04C07D409/04C09K11/06G01N21/64
Inventor 李猛王树冯丽恒陈传峰
Owner INST OF CHEM CHINESE ACAD OF SCI
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