Succinimide esters and methods of making, treating and detecting same

A technology of succinimide ester and triethylamine, which is applied in measurement devices, organic chemistry, instruments, etc., can solve the problems of inaccurate detection methods, low yield and purity of succinimide ester, and solve unstable problems. The effect of improving the stability, improving the purity and improving the reaction yield

Pending Publication Date: 2022-06-17
湖北华大基因研究院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0019] The technical problem to be solved by the present invention is that the preparation method yield and purity of succinimide ester are relatively low, and the detection method is inaccurate, etc.

Method used

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  • Succinimide esters and methods of making, treating and detecting same
  • Succinimide esters and methods of making, treating and detecting same
  • Succinimide esters and methods of making, treating and detecting same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0150]

[0151] Synthesis of AF532-NHS:

[0152] Compound AF532 (1000mg, 1.60mmol, 1eq), TEA (1618mg, 16.02mmol, 10eq) were added to a 50mL three-necked flask, dissolved in DMF (10mL), nitrogen was replaced three times, and the reaction system was cooled to -20 using an ice-salt bath. Below ~-10°C, TSTU (1442 mg, 4.79 mmol, 3 eq) was added in five or more times, each addition of about 300 mg, with an interval of 5 minutes. Under the protection of nitrogen, the condensation reaction was carried out at a temperature below -10 °C for 1 h.

[0153] Postprocessing:

[0154] The reaction was added dropwise to 150 mL of dry dichloromethane (1 mL of acetic acid was added to 150 mL of dichloromethane), the pH of the resulting solution was 6-7, and a small amount of solid was precipitated, then 50 mL of dry PE was added, and it was allowed to stand for 2h. A large amount of powdery solid was precipitated, filtered, and the filter cake was evacuated to constant weight at 30° C. and ...

Embodiment 2

[0168] Synthesis method of AF532-linker:

[0169]

[0170] A 250mL two-necked flask was connected with a tee with a nitrogen balloon, and AF532-NHS (9.60g, 13.275mmol) and anhydrous DMF (96mL) were added to the two-necked flask to completely dissolve into an orange solution, and then DIPEA (5.15g, 39.825mmol) was added. ). Take another 50mL single-neck bottle in advance to weigh Linker (9.75g, 26.550mmol), add anhydrous DMF (48mL), and dissolve it into a colorless transparent liquid. Then, it was added to the above reaction system at one time, nitrogen was replaced three times, and the reaction was stirred at room temperature for 1 h. The reaction solution was poured into 1 L of ethyl acetate, and a solid was precipitated, which was filtered to obtain 14 g of a reddish-brown solid.

[0171] The mass spectral data are as follows: (positive ion mode)

[0172] AF532-linker: 796.3.

[0173]

[0174] Synthesis of AF532-linker-NHS:

[0175] Compound AF532-linker (1400mg, ...

Embodiment 3

[0191]

[0192] Synthesis of ROX C4-NHS:

[0193] Compound ROX C4 (1000mg, 1.33mmol, 1eq), TEA (1343mg, 13.3mmol, 10eq) were added to a 50mL three-necked flask. After dissolving with DMF (10mL), nitrogen was replaced three times, and the reaction system was cooled to - Below 20~-10 ℃, TSTU (1464mg, 3.99mmol, 3eq) was added in five or more times, about 300mg was added each time, and each time was 5 minutes apart. Under nitrogen protection, the condensation reaction was carried out at a temperature below -10 °C for 1 h.

[0194] Postprocessing:

[0195] The reaction was added dropwise to 150 mL of dry dichloromethane (1 mL of acetic acid was added to 150 mL of dichloromethane), the pH of the resulting solution was 6-7, and a small amount of solid was precipitated, then 50 mL of dry PE was added, and it was allowed to stand for 2h. A large amount of powdery solid was precipitated, filtered, and the filter cake was evacuated to constant weight at 30° C. and 1 mbar to obtain a...

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Abstract

The invention provides succinimide ester as well as a preparation method, a treatment method and a detection method thereof. The preparation method of the succinimide ester comprises the following step: in the presence of triethylamine, carrying out condensation reaction on a compound A and TSTU in a solvent to obtain the succinimide ester. According to the preparation method, generation of impurities can be inhibited, the purity and the yield of the product are improved, and the difficulty of post-treatment purification is reduced; the product can be kept stable in the post-treatment process, so that the reaction yield is increased; in the detection method disclosed by the invention, a derivation method is adopted, and a detection sample is converted into a relatively stable amide or ester compound, so that the stability and accuracy of detection are ensured.

Description

technical field [0001] The present invention relates to succinimidyl esters and methods for their preparation, treatment and detection. Background technique [0002] Succinimide active esters are commonly used in fluorescent immunoassays, fluorescent probes, and cell staining. Including specific DNA staining, for chromosome analysis, cell cycle, apoptosis and other related research. Many other nucleic acid dyes are useful counterstains in multicolor staining systems as background controls, labeling nuclei so that the spatial relationships of intracellular structures can be seen at a glance. [0003] Fluorescently labeled monoclonal antibody technology in immunoassay expands infinite application space for flow cytometry in the study of cell membrane and intracellular various functional antigens, tumor gene proteins and other fields. Fluorescent probes can be covalently bound to monoclonal antibodies via protein cross-linkers. [0004] In nucleic acid detection, after the n...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/14C07D471/04C07D487/04G01N30/02G01N30/06G01N30/14G01N30/54G01N30/72
CPCC07D487/04C07D403/14C07D471/04G01N30/02G01N30/06G01N30/14G01N30/54G01N30/72G01N2030/027G01N2030/062G01N2030/146
Inventor 杨明三张少桥王明李汉东章文蔚
Owner 湖北华大基因研究院
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