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Fluorescein diacetate fluorescence probe containing aldehyde group structure and preparation method and application thereof

A fluorescein diacetate, fluorescent probe technology, used in fluorescence/phosphorescence, biochemical equipment and methods, chemical instruments and methods, etc., can solve problems such as unsolved problems, leakage of fluorescent products, etc. Achieve good chemical stability, good solubility and biocompatibility, and enhance the effect of specific selectivity

Inactive Publication Date: 2016-07-13
LIAONING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Fluorescein diacetate, aminofluorescein and isothiocyanate fluorescein have been used to label living cells, but the leakage of fluorescent products has not been well resolved

Method used

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  • Fluorescein diacetate fluorescence probe containing aldehyde group structure and preparation method and application thereof
  • Fluorescein diacetate fluorescence probe containing aldehyde group structure and preparation method and application thereof
  • Fluorescein diacetate fluorescence probe containing aldehyde group structure and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0021] Embodiment 1 A kind of preparation method of fluorescein diacetate fluorescent probe (A-FDA fluorescent probe) containing aldehyde structure

[0022] Add 1 mol of fluorescein monoaldehyde and 2 mol of potassium carbonate to 3 mol of ether, add 3 drops of dichloromethane until dissolved, add 5 ml of acetic anhydride dropwise, and react with magnetic stirring for 6 hours at room temperature, filter the reactant with suction, and remove the filtrate. Spin-dry, and purify by silica gel column chromatography to obtain a white solid, which is the target product A-FDA fluorescent probe.

[0023] HRMS: 444.0845.

[0024] The preparation reaction formula is as follows:

[0025]

[0026] Among them, the synthesis method of fluorescein monoaldehyde is as follows: take 2g of fluorescein in a flask, add 12ml of chloroform and 0.4ml of 15-crown-5 into the flask, slowly add NaOH solution dropwise to the flask, put it in an oil bath at 55°C, and react for 7 hours , take the produc...

Embodiment 2

[0033] Embodiment 2, A-FDA fluorescent probe measures soil hydrolytic enzyme

[0034] Take 2g of soil in a 125ml Erlenmeyer flask, add 15ml of phosphate buffer solution (pH=7.4, 60mM) into the Erlenmeyer flask, add 0.2ml of A-FDA solution (3mM) into the Erlenmeyer flask, and cultivate at 30°C Add a terminator (a mixed solution of chloroform and methanol at a volume ratio of 2:1) in 1h, take the sample in a 15ml centrifuge bottle, rotate at 2000, centrifuge for 3min, filter the supernatant, and test, the result is as follows: Figure 4 Ac 1 ; set the amount of the control group, one group is: take 2g of soil in the Erlenmeyer flask, add 15ml of phosphate buffer solution (pH=7.4, 60mM), add 0.2ml of acetone into the Erlenmeyer flask, culture at 30°C for 1h with constant temperature shaking, add Terminator, centrifuged to get the supernatant, tested, the results are as follows Figure 4 Ab 1 The other group is: add the same amount of phosphate buffer solution and 0.2ml A-FDA s...

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Abstract

The invention discloses a fluorescein diacetate fluorescence probe containing an aldehyde group structure and a preparation method and application thereof.The fluorescence probe is A-FDA, and the structural formula of A-FDA is shown in the formula (I).The A-FDA fluorescence probe is applied to indication for the activity of hydrolytic enzymes in living cells.By means of an aldehyde group in the probe, the lipophicity of the probe is improved, the specific selectivity of the probe is enhanced, reverse osmosis of hydrolyzed fluorescein generated after the probe enters the cells is relieved, and meanwhile good chemical stability, light stability, solubility and biocompatibility are achieved.A microimaging experiment shows that the probe has good cell targeting and permeability and has no toxic or side effect on the cells and organisms.The structural formula is shown in the description.

Description

technical field [0001] The invention relates to a fluorescein diacetate fluorescent probe containing an aldehyde structure and a preparation method and application thereof. Background technique [0002] The fluorophore of fluorescein is the most common fluorescent derivatization reagent for covalently labeling proteins. Fluorescein diacetate (FDA) hydrolysis is widely accepted as an accurate and simple measure of total microbial activity. This method has the advantages of simplicity, rapidity, and sensitivity, and fluorescein diacetate (FDA) hydrolysis is widely used as an indicator to measure the total microbial activity. It is used for plant cell staining, determination of pollen viability and in vitro cell viability detection, so the fluorescein staining and labeling of cells is widely used. Fluorescein diacetate (FDA) is the diacetate ester of fluorescein. It is more lipophilic than fluorescein and is easily absorbed by cells through the cell membrane. The fluorescenc...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D493/10G01N21/64C12Q1/02
CPCC07D493/10C09K11/06C09K2211/1088C12Q1/02G01N21/6428
Inventor 于海波李谷丽宋有涛方培菊吕春娇
Owner LIAONING UNIVERSITY
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