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Preparation method of fluorescein isothiocyanate derivative

A technology of fluorescein isothiocyanate and derivatives, applied in organic chemistry and other directions, to achieve the effects of good luminescence effect, high product purity and stable structure

Active Publication Date: 2021-07-16
艾克发(北京)生物技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, FITC usually needs to be coupled to detection molecules such as antibodies before it can be used, and cannot be used alone for the detection of biological materials

Method used

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  • Preparation method of fluorescein isothiocyanate derivative
  • Preparation method of fluorescein isothiocyanate derivative
  • Preparation method of fluorescein isothiocyanate derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] The preparation method of compound 1

[0059]

[0060] Reactions were performed in dry glassware under an argon atmosphere. The starting 4-(but-3-yn-1-yl)phenol alcohol (669 mg, 2.4 mmol, 1.0 equiv) was dissolved in anhydrous dichloromethane (10 mL) and washed with Et3 SiH (773 μL, 563 mg, 4.8 mmol, 2.0 eq) treated. The mixture was cooled to 0 °C, then BF was added 3 ·OEt 2 (613 μL, 687 mg, 4.8 mmol, 2.0 equiv) and the reaction was stirred at 0° C. for 1 hour. When TLC showed that the starting material was completely converted, another 4 equivalents of BF 3 ·OEt 2 (1.2 mL, 1.37 g, 9.6 mmol, 4.0 equiv), the mixture was warmed to room temperature and stirred for 18 hours. TLC showed complete conversion of the intermediate to the final product, the mixture was diluted with dichloromethane (50 mL) and washed with saturated NaHCO 3 (30 mL) aqueous solution. The aqueous layer was back extracted with dichloromethane (2×20 mL), the combined organic layers were washed ...

Embodiment 2

[0062] The preparation method of compound 3

[0063]

[0064] Dissolve 1,4-benzenediol (20mmol), propargyl bromide (10mmol) and potassium carbonate (15mmol) in acetonitrile (50mL) and react overnight at 50°C. The solvent was removed by rotary evaporation, and the target product 3 was obtained by separation by column chromatography.

Embodiment 3

[0066] The preparation method of compound 5

[0067]

[0068] 5 mmol of the compound 5-aminofluorescein (purchased from Aladdin, Lot No. H1801120) was dissolved in 100 mL of acetic acid / water (2:1), and 7.5 mmol of sodium nitrite was added at 0°C. After 15 minutes of reaction, 10 mmol of sodium azide was added, and the reaction was continued for 2 hours. After the reaction, the solvent was removed by rotary evaporation, and the crude product was washed successively with 200 mL of 2M hydrochloric acid and 1000 mL of water. TLC detection reaction. Purification by column chromatography (dichloromethane:methanol=8:1) gave product 5.

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Abstract

The invention provides a novel preparation method of fluorescein isothiocyanate derivatives. The fluorescein isothiocyanate derivative prepared by this method can be directly connected with the amino acid in the biological material, thereby forming a biomolecule labeled with the fluorescein isothiocyanate derivative, and then realizing the detection of the biological material.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a method for preparing fluorescein isothiocyanate derivatives. Background technique [0002] Fluorescein isothiocyanate (FITC) is obtained by adding isothiocyanate groups through chemical reactions on the basis of fluorescein. The thiocyanate group contained in FITC can react with the amino group of the amino acid in the biological material to form a thiourea bond, thereby realizing the fluorescent labeling of the biological material. For example, FITC can be combined with amino acids in various antibody molecules to form FITC-labeled antibody molecules. After the antibody binds to the antigen in the biological material to be detected, the corresponding antigen can be detected qualitatively, locally or quantitatively by observation under a fluorescent microscope or flow cytometry analysis. FITC is currently the most widely used fluorescein, and it has a wide range of uses in f...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/10
CPCC07D493/10
Inventor 彭作富
Owner 艾克发(北京)生物技术有限公司
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