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Solid-phase synthesis of asymmetric indocyanine dyes

A solid-phase synthesis, indocyanine technology, applied in the direction of organic dyes, chemical instruments and methods, methine/polymethine dyes, etc., can solve the problems of difficult purification, complicated operation, low yield, etc., to avoid by-products , The effect of increasing the purity of the product and simplifying the purification process

Inactive Publication Date: 2007-09-05
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This liquid-phase synthesis method is complex in operation and low in yield, and the final product is a mixture of symmetric and asymmetric indocyanine dyes, which is difficult to purify

Method used

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  • Solid-phase synthesis of asymmetric indocyanine dyes
  • Solid-phase synthesis of asymmetric indocyanine dyes
  • Solid-phase synthesis of asymmetric indocyanine dyes

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Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0031] The synthetic steps of unsymmetrical indocyanine dye Cy3 are as follows:

[0032] Step 1. Preparation of Polyethylene Glycol-2000 Supported Monomethyl Electrophile

[0033] 3.02 g (1.35 mmol) of aniline loaded on polyethylene glycol-2000 and 10 ml (60 mmol) of triethyl orthoformate were dissolved in 27 ml of glacial acetic acid, and reacted at 55° C. for 5.5 hours under electromagnetic stirring. After cooling to room temperature, 50ml of ether was added to the reaction liquid, stirred electromagnetically for 5 minutes, then allowed to stand for 10-20 minutes, and filtered to obtain 2.43g of primary methyl electrophile loaded on polyethylene glycol-2000 as a pale yellow solid. The rate is 80.1%. IR (KBr): v3446, 2884, 1701, 1638, 1604, 1529cm-1 . 1 H NMR (300MHz, CDCl 3 ): δ8.53 (s, 1H), 8.14 (d, 4H), 7.27 (d, 4H), 3.3-4.5 (m, polyethylene glycol). The reaction formula is as follows:

[0034]

[0035] PEG in the above reaction formula is polyethylene glycol carri...

preparation Embodiment 2

[0043] The synthetic steps of unsymmetrical indocyanine dye Cy5 are as follows:

[0044] Step 1 Preparation of polyethylene glycol-2000-loaded trimethyl electrophile

[0045] Dissolve 2.02g (0.90mmol) of aniline loaded on polyethylene glycol-2000, 3.7mL (22.2mmol) of 1,1,3,3-tetramethoxypropane in 9mL of glacial acetic acid, and react at 55°C for 5.5 hours under electromagnetic stirring . After cooling to room temperature, 30 mL of diethyl ether was added to the reaction solution, stirred electromagnetically for 5 minutes, then allowed to stand for 10 to 20 minutes, and filtered to obtain 1.56 g of trimethyl electrophile loaded on polyethylene glycol-2000 as a yellow solid, with a yield of 73.0%. . IR (KBr): v3437, 2886, 1706, 1639, 1601, 1465cm -1 . 1 H NMR (300MHz, CDCl 3 ): δ8.06 (m, 3H), 7.85 (d, 1H), 7.11 (d, 2H), 6.65 (dd, 1H), 3.3-4.5 (m, polyethylene glycol). The reaction equation is as follows:

[0046]

[0047] Step 2 Preparation of Polyethylene Glycol-2000...

preparation Embodiment 3

[0054] The synthetic steps of unsymmetrical indocyanine dye Cy3 are as follows:

[0055] Step 1 Preparation of Polyethylene Glycol-1000-loaded Monomethyl Electrophile

[0056] 1.67 g (1.35 mmol) of aniline loaded on polyethylene glycol-1000 and 10 mL (60 mmol) of triethyl orthoformate were dissolved in 27 mL of glacial acetic acid, and reacted at 55° C. for 5.5 hours under electromagnetic stirring. Cool in an ice bath to 0-5°C, then add 50 mL of diethyl ether to the reaction solution, stir it electromagnetically for 5 minutes, then continue to stand in the ice bath for 10-20 minutes, and filter to obtain a light yellow solid polyethylene glycol-1000-loaded primary Methyl electrophile 1.20g, yield 71.2%.

[0057] Step 2 Preparation of Polyethylene Glycol-1000 Loaded Dimethyl Hemicyanine Dye

[0058] 1.31g (1.05mmol) of primary methyl electrophile loaded on polyethylene glycol-1000, 0.28g (1.05mmol) of 1-ethyl-2,3,3-trimethylindole-5-sulfonate and 0.34 mL (2.08 mmol) of triet...

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Abstract

Solid-phase synthesis of asymmetric indocyanine dye is carried out by preparing methine-electrophilic agent with polyethylene as carrier, reacting carried electrophilic agent with nucleophilic 1-bit substitute 2-methyl indole or its derivative to obtain carried semi-dicyan dye, attacking 1-bit substitute 2-methyl indole or its derivative with nucleophilic carbon atom to carried semi-dicyan dye and nucleophilic reacting to obtain the final product. It costs low and has short production period, high purity and no need for chromatography separation.

Description

technical field [0001] The invention relates to a solid-phase synthesis method of near-infrared asymmetric indocyanine dyes. Background technique [0002] Indocyanine dyes (Cy for short) are an important class of cyanine dyes. Because of its large molar extinction coefficient, good fluorescence performance, increased fluorescence efficiency after being combined with the matrix, large adjustable range of maximum absorption wavelength, and relatively high stability, it is used in infrared laser dyes, CD storage materials, Bioanalysis, nucleic acid and protein labeling have been widely used. The basic structure of common indocyanine dyes is shown in formula (1). [0003] [0004] According to the number of methine groups in the molecule, it can be divided into indole monocyanine (one methyl cyanine), indole carbocyanine (trimethyl cyanine), indole dicarbocyanine (penta cyanine), indole tricarbocyanine (seven In addition, according to whether the two heterocycles in the mo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/16
Inventor 李宝林窦丽芳蒋林玲
Owner SHAANXI NORMAL UNIV
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