Water-soluble asymmetric indocyanine fluorescent dye and preparation method thereof

A fluorescent dye, asymmetric technology, used in organic dyes, luminescent materials, chemical instruments and methods, etc., can solve the problems of many side reactions, fluorescence quenching, fluorescence intensity drop, etc., to achieve strong light stability and fluorescence intensity, The effect of high fluorescence quantum yield and reduction of self-aggregation tendency

Inactive Publication Date: 2013-05-01
HENAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, there are still many deficiencies in water-soluble asymmetric cyanine dyes, such as: 1) the molecular polarity of asymmetric water-soluble indocyanine dyes is usually large, and there are many side reactions during synthesis; by-products have similar polarities, and the separation of products Purification is quite difficult
2) Most of the products on the market rely on foreign imports, which are expensive
In indocyanine dyes, the longer the conjugated methine chain of the molecule, the less stable the dye
Trimethine indocyanine dyes can be stored f

Method used

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  • Water-soluble asymmetric indocyanine fluorescent dye and preparation method thereof
  • Water-soluble asymmetric indocyanine fluorescent dye and preparation method thereof
  • Water-soluble asymmetric indocyanine fluorescent dye and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Water-soluble asymmetric indocyanine fluorescent dye (Cy5-671), its structure is:

[0034]

[0035] The following are the synthetic route diagram and specific preparation method of the compound:

[0036] (1) Synthetic roadmap

[0037]

[0038]

[0039] (2) Preparation method

[0040] (1) Synthesis of intermediate A2,3,3-trimethyl-5-sulfonic acid-3H-indole

[0041] Add 20mL of acetic acid, 5.0g (0.026mol) of 4-sulfophenylhydrazine and 6.0mL (0.052mol) of 3-methyl-2-butanone into a 50mL three-necked flask in sequence, and react at 80°C under argon protection for 2.0 h, acetic acid was distilled off under reduced pressure, dissolved in 20 mL of methanol and then added with 100 mL of acetone to precipitate a pink solid, namely intermediate A, with a yield of about 57%.

[0042] (2) Synthesis of Intermediate B N-p-carboxybenzyl-2,3,3-trimethyl-5-sulfonic acid-3H-indole

[0043] Add 20mL of toluene, 1.0g (0.0042mol) of intermediate A, 0.4g (0.0042mol) of potassium ...

Embodiment 2

[0073] Water-soluble asymmetric indocyanine fluorescent dye (Cy3-567), its structure is:

[0074]

[0075] The preparation method is:

[0076] (1) N-(3,5-bis(2-(2-methoxyethoxy)ethoxy)ethoxy)benzyl-2,3,3-trimethyl-5-sulfonic acid group- Synthesis of 3H-indole

[0077] Add 30mL ethanol, 0.0042mol2,3,3-trimethyl-5-sulfonic acid group-3H-indole, 0.0126mol potassium acetate and 0.0126mol3,5-bis(2-(2- Methoxyethoxy)ethoxy)ethoxybenzyl bromide, reflux reaction under argon protection for 20h, after the reaction, ethanol was rotary evaporated, and the methanol / dichloromethane mixed solvent with a volume ratio of 1:2 was used as the washing The solvent was removed, and the crude product was separated with a silica gel-filled separation column to obtain a red solid product with a yield of 61%.

[0078] (2) Synthesis of the target product

[0079]Add 6.0mL acetic acid, 6.0mL acetic anhydride, 0.0015mol N-p-carboxybenzyl-2,3,3-trimethyl-5-sulfonic acid-3H-indole, 0.0015mol N ,N′-D...

Embodiment 3

[0085] Water-soluble asymmetric indocyanine fluorescent dye Cy7, the structure is:

[0086]

[0087] Its preparation method is as follows:

[0088] (1) N-(3,5-bis(2-(2-methoxyethoxy)ethoxy)ethoxy)benzyl-2,3,3-trimethyl-5-sulfonic acid group- Synthesis of 3H-indole

[0089] Add 30mL methanol, 0.0042mol2,3,3-trimethyl-5-sulfonic acid group-3H-indole, 0.0042mol potassium acetate and 0.0042mol3,5-bis(2-(2- Methoxyethoxy) ethoxy) ethoxybenzyl bromide, reflux reaction under the protection of argon for 40h, after the reaction, methanol was rotary evaporated, and the methanol / dichloromethane mixed solvent with a volume ratio of 1:2 was used as the washing The solvent was removed, and the crude product was separated with a silica gel-filled separation column to obtain a red solid product with a yield of 61%.

[0090] (2) Synthesis of the target product

[0091] Add 6.0mL acetic acid, 6.0mL acetic anhydride, 0.0015mol N-p-carboxybenzyl-2,3,3-trimethyl-5-sulfonic acid-3H-indole, 0...

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Abstract

The invention discloses a water-soluble asymmetric indocyanine fluorescent dye. A general formula of the dye is as shown in the specification, wherein n is equal to 1, 2 or 3. A preparation method comprises the steps that (1), N-(3,5-2(2-(2-methoxyethoxy) oxethyl) oxethyl) benzyl-2,3,3-trimethyl-5-sulfonic group-3H-indole is synthesized; 2,3,3-trimethyl-5-sulfonic group-3H-indole, organic sylvine, and 3,5-2(2-(2-methoxyethoxy) oxethyl) oxethyl) oxethyl benzylbromide are added to an alcohol solvent in sequence, and conduct backflow reaction for 20-40h under inert gas shielding; the solvent is distilled off after the reaction; column separation is conducted; a red solid product is obtained; and (2), N-carboxyl benzyl-2,3,3-trimethyl-5-sulfonic group-3H-indole, the product and a condensing agent are dissolved in an acetic acid/acetic anhydride mixed solvent; pyridine or pyrimidine is added, and reacts at 60-100 DEG C for 1-6h under the inert gas shielding; ethyl acetate is added after the reaction for dissolving out a precipitate; suction filtration is conducted; the product is separated by taking a methanol/acetonitrile mixed solvent as an eluent, and using a reverse phase silica gel filling separation column; three color strips are obtained; the second color strip is accepted; and the water-soluble asymmetric indocyanine fluorescent dye is obtained.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and in particular relates to a water-soluble asymmetric indocyanine fluorescent dye containing an ether chain structure, and also relates to a preparation method of the fluorescent dye. Background technique [0002] Williams discovered cyanine dyes (also known as cyanines) in 1856. In 1873, Vogel discovered that such dyes had exceptionally sensitive photosensitivity. Since then, cyanine dyes have been used in biological analysis, chemical analysis, spectral sensitization, solar cells, etc. Applied research is changing with each passing day. Cyanine dyes have a wide spectral range (550nm ~ 1200nm), high molar extinction coefficient (up to 10 5 L·mol -1 cm -1 ), high fluorescence quantum yield, high selectivity, and high sensitivity. With the rapid development of biotechnology and fluorescent labeling technology, cyanine dyes have been widely used in the analysis and detection of DNA, protein a...

Claims

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Application Information

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IPC IPC(8): C09B23/08C09K11/06
Inventor 张付利汤昆贾春辉胡海廷邱娜张潇晗王运聚
Owner HENAN UNIVERSITY
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