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Synthesis method of water-soluble squarylium indocyanine multifunctional cell fluorescent dye

A technology of indole squaraine and fluorescent dyes, which is applied in the field of synthesis of squaraine, can solve the problems of poor water solubility and wide application, and achieve the effects of easy fluorescence imaging, broad application prospects, and strong fluorescence

Active Publication Date: 2013-04-10
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the disadvantages of indole squaraine dyes such as easy aggregation and poor water solubility limit its wide application in biology.

Method used

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  • Synthesis method of water-soluble squarylium indocyanine multifunctional cell fluorescent dye
  • Synthesis method of water-soluble squarylium indocyanine multifunctional cell fluorescent dye
  • Synthesis method of water-soluble squarylium indocyanine multifunctional cell fluorescent dye

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Organic synthesis of indole squaraine dyes functionalized with primary amino groups.

[0032] 1) Add p-carboxyphenylhydrazine hydrochloride (5.66 g, 30 mmol) and 3-methyl-2-butanone (9.6 mL, 90 mmol) (molar ratio 1:3) into the reaction flask, and add solvent Glacial acetic acid 20 ml. The solution was heated to reflux temperature under nitrogen atmosphere and reacted for 12 hours to obtain 3H-indoline product.

[0033] 2) Add 3H-indoline (0.82 g, 4 mmol) and p-carboxybenzyl bromide (0.86 g, 4 mmol) (1:1 molar ratio) into the reaction flask, and add 10 ml of solvent acetonitrile. The solution was heated to reflux temperature under a nitrogen atmosphere, and reacted for 24 hours to obtain quaternized indoline derivatives.

[0034] 3) Add indoline derivatives (836 mg, 2 mmol) and squaraine (114 mg, 1 mmol) (molar ratio 1:0.5) into the reaction flask, and add 12 ml of solvent (n-butanol:toluene:pyridine =1:1:1), reflux reaction under nitrogen atmosphere for 24 h...

Embodiment 2

[0038] Example 2: Organic synthesis of indole squaraine dyes functionalized with tertiary amino groups.

[0039] 1) Implementation steps 1-3 are the same as implementation example 1.

[0040] 4) Add carboxy-functionalized squaraine (301.2 mg, 0.4 mmol), HATU (1.52 g, 4 mmol) and DIPEA (1.32 mL, 8 mmol) (molar ratio 1:10:20) into the reaction flask, and Add solvent DMF 10 ml, stir at room temperature under nitrogen atmosphere for 10 minutes, then add N, N'-dimethylethylenediamine (282 mg, 3.2 mmol) and react for 0.5 hours to obtain tertiary amino functionalized indole squaraine dye. Its structural formula is as follows:

[0041]

Embodiment 3

[0042] Implementation Example 3: This type of dye specifically marks the cell membrane of living tissue cells.

[0043] The dyes were incubated with living cells of Drosophila and salivary gland tissues of transgenic Drosophila for 1 hour. The dyes could specifically label the cell membranes of the cells and overlap well with the cell membranes expressing green fluorescent protein.

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Abstract

The invention discloses a synthesis method of a water-soluble squarylium indocyanine multifunctional cell fluorescent dye. The dye is prepared through multi-step chemical synthesis, and finally, squarylium indocyanine contains cationic amine functional groups, thereby improving the water solubility and biocompatibility of the squarylium cyanine. The fluorescent molecule can interact with DNA (deoxyribonucleic acid) in cell nuclei or phospholipid molecules in cell membranes, thereby specifically marking cell membranes of living cells and cell nuclei of fixed / dead cells. By combining the two cell marking characteristics, the fluorescent dye can successfully mark cell nuclei of cells which are being subjected to apoptosis in living tissues. According to the invention, the method is mature in synthesis process and simple to operate; and the product has the advantages of safety, no toxicity, high molecule designability, excellent water solubility, favorable light stability, high pH-sensitivity and the like, and can be used as a multifunctional cell fluorescent marking molecule in scientific study, diagnosis and production in the biomedicine field.

Description

technical field [0001] The invention belongs to the field of organic dye synthesis and biological cell labeling, in particular to a method for synthesizing cationic amino-functionalized squaraine with a designable structure. Background technique [0002] Cyanine dyes are a special class of dyes. Unlike traditional dyes, they cannot be used for fabric dyeing because they are unstable under light. In fact, in the initial research stage, cyanine dyes have been used as a photosensitive material and a sensitizer for silver halide gels for a long time. So far, its application in the field of photosensitive materials still occupies an important position, especially in recent years it has been widely used as a new type of optical storage medium in organic storage discs. For example, in the photosensitive layer material of CD-ROM disc, cyanine dye is one of the three most commonly used dyes at present. [0003] In order to meet the ever-changing needs of fluorescent dyes for biolog...

Claims

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Application Information

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IPC IPC(8): C09B23/10C09K11/06C12Q1/68C12Q1/04
Inventor 尹梅贞李杰郭坤茹杨万泰孙盟盟沈杰
Owner BEIJING UNIV OF CHEM TECH
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