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A coded microsphere containing cyanine compounds and its preparation method and application

A technology for encoding microspheres and compounds, which is applied in the field of new applications of cyanine compounds, can solve the problems of the limited number of fluorescent signal uniformity coding, the difficulty of selecting fluorescent dyes, and the unpredictable coding signal, etc., and achieves a large and uniform coding range Good performance and good stability

Active Publication Date: 2022-04-29
北京指真生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the encoding signal after encoding the microspheres cannot be predicted, cannot be accurately designed, and the uniformity of the fluorescent signal and the number of encodings are also limited, all of which increase the difficulty for the selection of fluorescent dyes

Method used

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  • A coded microsphere containing cyanine compounds and its preparation method and application
  • A coded microsphere containing cyanine compounds and its preparation method and application
  • A coded microsphere containing cyanine compounds and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0119] Preparation example 1 (preparation of compound I):

[0120]

[0121] 40mmol 2,3,3-trimethylindole, 80mmol propenyl iodide and 20mL xylene, heated to reflux under nitrogen protection, reacted for 24 hours, cooled to room temperature, added 200mL ether, filtered, and washed with appropriate amount of ether , to obtain a solid intermediate product;

[0122] Take 6 mmol of the solid intermediate product, 2 mmol of squaraine, 8 mL of toluene, 6 mL of n-butanol, and 6 mL of pyridine, stir and heat to reflux under the protection of argon, and stop the reaction after 6 hours. After cooling to room temperature, appropriate amount of solvent was distilled off under reduced pressure. 200 mL of diethyl ether was added thereto to precipitate the product, which was filtered, washed with diethyl ether and dried to obtain an unpurified solid product.

[0123] The unpurified solid product was purified by silica gel column chromatography, and was eluted with a gradient of eluent eth...

preparation example 2

[0124] Preparation example 2 (preparation of compound II):

[0125]

[0126] 40mmol 1,1,2-trimethyl-1H-benzo[e]indole, 80mmol 1-bromopropane and 25mL o-dichlorobenzene were heated to reflux under the protection of argon, reacted for 40 hours, cooled to room temperature, 200 mL of ethyl acetate was added thereto, and the product was precipitated by ultrasonic oscillation, filtered, and washed to obtain a solid intermediate product;

[0127] Take 6 mmol of the solid intermediate product, 2 mmol of squaraine, 8 mL of toluene, 6 mL of n-butanol, and 6 mL of pyridine, stir and heat to reflux under the protection of argon, and stop the reaction after 6 hours. After cooling to room temperature, part of the solvent was distilled off under reduced pressure. 200 mL of diethyl ether was added thereto to precipitate the product, which was filtered, washed with diethyl ether and dried to obtain an unpurified solid product.

[0128] The unpurified solid product was purified by silica g...

preparation example 3

[0130] Preparation example 3 (preparation of compound III):

[0131]

[0132] 40mmol 2,3,3-trimethylindole, 80mmol 6-bromohexanoic acid ethyl ester and 25mL o-dichlorobenzene were heated to reflux under argon protection, reacted for 24 hours, cooled to room temperature, and 150mL acetic acid was added to it Ethyl ester, ultrasonic vibration to precipitate the product, grind in ethyl acetate and filter to obtain a dark brown-red block intermediate product;

[0133] Take 6 mmol of the brown-red intermediate product, 2 mmol of squaraine, 8 mL of benzene, 6 mL of n-butanol, and 6 mL of pyridine, stir and heat to reflux under the protection of argon, and stop the reaction after 6 hours. After cooling to room temperature, 200 mL of diethyl ether was added to precipitate the product, filtered, washed with diethyl ether and dried to obtain a dark blue solid.

[0134] The dark blue solid was purified by silica gel column chromatography, and the eluent was ethyl acetate:petroleum et...

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Abstract

The present application relates to the technical field of fluorescent coding microspheres, and discloses a coding microsphere containing cyanine compounds and a preparation method and application thereof. An encoded microsphere containing a cyanine compound, the encoded microsphere comprises: a cyanine compound, a microsphere, and a sealing layer, the cyanine compound is inside the microsphere, and the sealing layer is the outermost layer. The preparation method includes the following steps: dispersing the microspheres in a solvent to obtain a microsphere suspension; dissolving cyanine compounds in the solvent to obtain a dye solution; adding the dye solution into the microsphere suspension; and coating a sealing layer. Application of encoded microspheres containing cyanine compounds in the preparation of biological detection reagents for detecting antigens / antibodies and nucleic acids. In the present application, a series of encoded microspheres with different fluorescence intensities are obtained by controlling the amount of cyanine compounds added or the number of added compounds.

Description

technical field [0001] The present application relates to the field of new applications of cyanine compounds, in particular to coded microspheres containing cyanine compounds and their preparation methods and applications. Background technique [0002] Fluorescence-encoded microspheres (also known as fluorescent-labeled microspheres) technology has been widely used in multi-index joint detection of immune and nucleic acid projects. Its working principle is: using polymer microspheres as the solid carrier of immunoadsorption analysis of dyes, dyeing and marking the microspheres by using fluorescent substances of different wavelengths or using different concentrations of the same fluorescent substance, so that the microspheres have unique fluorescent signals Microspheres with specific antigens / antibodies or DNA fragments coupled on the surface of the microspheres are encoded, and each optical signal points to a specific analyte, which can be used for multiple detection after m...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): G01N21/64
CPCG01N21/6428G01N21/6486G01N2021/6432
Inventor 刘燕徐兵马永波
Owner 北京指真生物科技有限公司
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