A kind of lipophilic fluorescein probe and preparation method thereof

A fluorescein and lipophilic technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., to achieve high affinity, not easy to self-hydrolyze, and easy to operate

Active Publication Date: 2022-07-22
TIANJIN QUANHECHENG TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is still room for further improvement in the affinity of the fluorescein probe to lipase and the minimum detection limit

Method used

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  • A kind of lipophilic fluorescein probe and preparation method thereof
  • A kind of lipophilic fluorescein probe and preparation method thereof
  • A kind of lipophilic fluorescein probe and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] The following methods were used to prepare lipophilic fluorescein probes according to the present application:

[0056]

[0057] (1) slowly add the oxalyl chloride of 35g in the 5-bromo-4-methylvaleric acid of 10g, then react at room temperature for 5 hours, after the completion of the reaction, under reduced pressure distillation at 80 ℃, obtain the product 5-bromo- of 10.33g- 4-Methylvaleryl chloride;

[0058] (2) 17.68g (0.05321mol) of fluorescein was added to 110mL (145.8g) of dichloromethane, the 5-bromo-4-methylvaleryl chloride obtained in step (1) was slowly added under stirring at room temperature, and then heated to reflux The reaction was performed for 5 hours, washed with saturated aqueous sodium bicarbonate solution after the reaction was completed, and the organic phase was distilled under reduced pressure at 40° C. The residue was washed with ethanol, and then dried at 55° C. for 3 hours to obtain 28.08g of product two ( 5-Bromo-4-methylvaleric acid) f...

Embodiment 2

[0061] The following methods were used to prepare lipophilic fluorescein probes according to the present application:

[0062]

[0063] (1) slowly add the oxalyl chloride of 30g in the 6-bromohexanoic acid of 10g, then react at room temperature for 3.5 hours, after the completion of the reaction, under reduced pressure distillation at 75 ℃, obtain the product 6-bromohexanoyl chloride of 10.11g;

[0064] (2) 19.67 g (0.05919 mol) of fluorescein was added to 140 mL (185.5 g) of dichloromethane, the 6-bromohexanoyl chloride obtained in step (1) was slowly added under stirring at room temperature, and then heated under reflux for 6 hours to react. After completion, it was washed with saturated aqueous sodium bicarbonate solution, and the layers were separated. The organic phase was distilled under reduced pressure at 45 °C, the residue was washed with methanol, and then dried at 55 °C for 3.5 hours to obtain 26.27 g of the product bis(6-bromohexanoic acid) ) fluorescein ester; ...

Embodiment 3

[0067] The following methods were used to prepare lipophilic fluorescein probes according to the present application:

[0068]

[0069] (1) slowly add the thionyl chloride of 40g to the 6-bromo-5-methylhexanoic acid of 10g, then react at room temperature for 2 hours, after the completion of the reaction, distillation under reduced pressure at 70° C. to obtain 10.41g of product 6- bromo-5-methylhexanoyl chloride;

[0070] (2) 15.96g (0.04803mol) of fluorescein was added to 100mL (132.5g) of dichloromethane, the 6-bromo-5-methylhexanoyl chloride obtained in step (1) was slowly added under stirring at room temperature, and then heated to reflux The reaction was carried out for 2 hours, washed with saturated aqueous sodium bicarbonate solution after the reaction was completed, and the organic phase was distilled under reduced pressure at 45° C. The residue was washed with methanol, and then dried at 60° C. for 4 hours to obtain 26.71 g of product two ( 6-Bromo-5-methylhexanoic...

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Abstract

The present application relates to the field of lipophilic fluorescein probes, and specifically discloses a lipophilic fluorescein probe and a preparation method thereof. The lipophilic fluorescein probe according to the present application is represented by the following chemical formula 1, wherein, R is a C1-C20 alkylene or cycloalkylene; R' is a C1-C20 alkyl, cycloalkyl, aralkyl , arylcycloalkyl, alkaryl or cycloalkaryl. The lipophilic fluorescein probe has high stability and is not easy to self-hydrolyze, but can be rapidly hydrolyzed to release fluorescein under the action of lipase, so it has a very high affinity for lipase and a very low detection rate. limit. In addition, the preparation method according to the present application has simple operation and high yield. [Chemical formula 1]

Description

technical field [0001] The present application relates to the field of lipophilic fluorescein probes, and more particularly, to a lipophilic fluorescein probe and a preparation method thereof. Background technique [0002] Fluorescein, also known as: fluorescent yellow, fluorescent raw, fluorescent red, English name: fluorescein, molecular formula: C 20 H 12 O 5 , molecular weight: 332.31, CAS number: 2321-07-5. In 1871, Baye synthesized fluorescein for the first time by the condensation of resorcinol and phthalic acid under the catalysis of zinc chloride, because of its high molar Extinction coefficient, excitation and emission wavelengths are all in the visible light region, high fluorescence quantum yield in water, non-toxic, low cost and other advantages, so it is widely used in biochemistry, medicine and medicinal chemistry research. Fluorescein is a xanthene dye with two isomers of lactone (yellow) and quinone (red) (as shown below), the chemical names are: 3',6'-di...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/6561C09K11/06G01N21/64
Inventor 宋艳民陈勇张超
Owner TIANJIN QUANHECHENG TECH
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