Silicon-based rhodamine fluorescent staining reagent as well as preparation method and application thereof

A silicon-based rhodamine and fluorescent dyeing technology, applied in the fields of immunology, organic chemistry and biochemistry, can solve the problem of small Stokes shift of antibody-labeled dyes and difficult application

Active Publication Date: 2021-01-22
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The object of the present invention is to provide a fluorescent dye based on a large Stokes shift of a rhodamine derivative skeleton substituted by a silicon atom, a high fluorescence intensity,

Method used

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  • Silicon-based rhodamine fluorescent staining reagent as well as preparation method and application thereof
  • Silicon-based rhodamine fluorescent staining reagent as well as preparation method and application thereof
  • Silicon-based rhodamine fluorescent staining reagent as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0106] The present embodiment has the preparation method of the silicon-based rhodamine fluorescent dyeing reagent of formula (I), comprising the following steps:

[0107] (1) Synthesis of intermediate A1

[0108] The synthetic route is as follows:

[0109]

[0110] m-Bromoaniline (1.0 mmol), 1,4-dibromobutane (1.5 mol) and potassium carbonate (3.0 mmol) were mixed and stirred in acetonitrile (5 mL) for 12 hours, then 100 mL of water was added. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (30 mL×3). The organic extracts were washed with brine and treated with Na 2 SO 4 dry. After the solvent was removed and distilled under reduced pressure, it was purified by 200-300 mesh silica gel column chromatography. Eluted with petroleum ether / ethyl acetate (20:1), the intermediate A1 was obtained as a light yellow liquid with a yield of 68%.

[0111] (2) Synthesis of Intermediate A2

[0112] The synthetic route is as follows:

[0113...

Embodiment 2

[0137]This example is basically the same as Example 1, except that the starting material is replaced by the B intermediate obtained by 6-bromoindole, and its synthetic route is shown in Figure 1 (b), which includes the following steps:

[0138] (1) Synthetic Intermediate B1

[0139] The synthetic route is as follows:

[0140]

[0141] 6-Bromoindole (1.0 mmol), iodomethane (1.5 mol) and potassium carbonate (2.0 mmol) were mixed and stirred in acetonitrile (5 mL) for 12 hours, then 100 mL of water was added. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (30 mL×3). The organic extracts were washed with brine and treated with Na 2 SO 4 dry. After the solvent was removed and distilled under reduced pressure, it was purified by 200-300 mesh silica gel column chromatography. Eluted with petroleum ether / ethyl acetate (10:1), the intermediate B1 was obtained as a light yellow liquid with a yield of 75%.

[0142] (2) Synthesis of interm...

Embodiment 3

[0171] This example is basically the same as Example 1, except that the starting material is replaced by the C intermediate prepared by m-bromoaniline, and its synthetic route is shown in Figure 1 (c), which includes the following steps:

[0172] (1) Synthesis of intermediate C1

[0173] The synthetic route is as follows:

[0174]

[0175] m-Bromoaniline (1.0 mmol), acetone (10 mol) and iodine (0.01 mmol) were mixed and stirred in acetonitrile (5 mL) for 12 hours, and then 100 mL of water was added. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (30 mL×3). The organic extracts were washed with brine and treated with Na 2 SO 4 dry. After the solvent was removed and distilled under reduced pressure, it was purified by 200-300 mesh silica gel column chromatography. Eluted with petroleum ether / ethyl acetate (10:1), the intermediate C1 was obtained as a light yellow liquid with a yield of 47%.

[0176] (2) Synthetic intermediate C2 ...

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Abstract

The invention discloses a silicon-based rhodamine fluorescent staining reagent as well as a preparation method and application thereof, and belongs to the field of organic chemistry and biochemistry.According to the silicon-based rhodamine fluorescent staining reagent as well as preparation method and application thereof of the invention, a silicon atom substituted rhodamine derivative is used asa basic frame, and is modified with aromatic amines in different forms, so that the silicon-based rhodamine fluorescent staining reagent which has large Stokes shift and high fluorescence intensity and can mark immunoglobulin IgG can be synthesized, so that the silicon-based rhodamine fluorescent staining reagent can be used for in-vitro SARS-CoV2-virus specific antibody fluorescence ELISA detection. The silicon-based rhodamine fluorescence staining reagent has large Stokes shift (greater than 140 nm), can effectively avoid mutual interference of excitation light and emitted light, and is high in detection sensitivity; a fluorescence ELISA detection method established based on the fluorescence antibody can be suitable for microplate readers with different bandwidths, and is wide in application range.

Description

technical field [0001] The invention relates to the fields of organic chemistry and biochemistry, in particular to the technical field of immunology, and in particular to a silicon-based rhodamine fluorescent staining reagent and its preparation method and application. Background technique [0002] SARS-CoV-2 virus is a novel coronavirus pathogen that caused 2019 Severe Acute Respiratory Syndrome (SARS). The main clinical manifestations of infected patients are respiratory symptoms and pneumonia. In February 2020, the Drug International Virus Taxonomy Committee officially named the virus SARS-CoV-2, and the World Health Organization (WHO) named the disease 2019 coronavirus disease (2019corona virusdisease, COVID-19). The SARS-CoV-2 virus has strong transmission ability, long incubation time, and high incidence rate. Traditional virus defense measures are not effective in controlling the virus. The global pandemic trend is obvious, and the situation of virus prevention and co...

Claims

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Application Information

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IPC IPC(8): C09B57/00C07F7/08C09K11/06G01N33/569G01N33/533
CPCC09B57/00C07F7/0816C09K11/06G01N33/56983G01N33/533C09K2211/1029C09K2211/1055C09K2211/1096G01N2333/165G01N2469/20
Inventor 李坤张宏刘艳红余孝其
Owner SICHUAN UNIV
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