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BODIPY-based high-sensitivity fluorescent probe and synthesis method and application thereof

A technology of fluorescent probe and synthesis method, which is used in biological analysis and imaging applications, and the synthesis of high-sensitivity fluorescent probes, which can solve the problems of insufficient cell membrane permeability and poor water solubility.

Inactive Publication Date: 2017-12-01
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Based on this characteristic, many fluorescent probes targeting such organelles have been developed. However, due to the high lipid solubility of triphenylphosphine, it has disadvantages such as poor water solubility and insufficient cell membrane permeability.

Method used

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  • BODIPY-based high-sensitivity fluorescent probe and synthesis method and application thereof
  • BODIPY-based high-sensitivity fluorescent probe and synthesis method and application thereof
  • BODIPY-based high-sensitivity fluorescent probe and synthesis method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The synthesis route of BODIPY mother core is as follows:

[0036]

[0037] The synthesis method is as follows:

[0038] Under an ice-water bath, methanol (1.60 g, 50.0 mmol) was slowly added dropwise to oxalyl chloride (6.35 g, 50.0 mmol) in dichloromethane (CH 2 Cl 2 , 100 mL) solution, then stirred at room temperature for 30 min, and the solvent was removed by rotary evaporation, and the obtained methyl oxalyl chloride was directly used in the next reaction. Dissolve 2,4-dimethylpyrrole (7.14g, 75.0mmol) in dichloromethane (140mL), cool to -78°C, slowly add methyl oxalyl chloride (3.67g, 30.0mmol) in dichloromethane (80mL) solution, then continued stirring at -78°C for 2h, and slowly added triethylamine (Et 3 N, 12.14g, 120.0mmol), boron trifluoride ether (BF 3 ·Et 2 (0, 22 mL), raised to room temperature, and continued to stir for 2h. The solvent was removed by rotary evaporation, and B-Me (3.67 g, yield 40.0%) was isolated by passing through the column with...

Embodiment 2

[0040] The synthetic routes of Alk-Ba and Azide-tpp are as follows:

[0041]

[0042] The synthesis method is as follows:

[0043] Stir 3,4-dihydroxybenzaldehyde (2.76g, 20.0mmol), potassium carbonate (2.76g, 20.0mmol) in acetone (30mL) for 10min, and slowly add propargyl bromide (2.38g, 20.0mmol) dropwise at room temperature ) in acetone (50 mL) for two hours and stirred for 14 hours. Filtrate, spin evaporate the filtrate to remove acetone, dissolve with ethyl acetate (100mL), wash with distilled water (100mL) and saturated sodium chloride solution (100mL) successively once, the organic layer is dried with anhydrous sodium sulfate, spin evaporate to remove solvent, use The dichloromethane:petroleum ether mixed solvent with a volume ratio of 1:1 was passed through the column as an eluent, and 3-hydroxy-4-propargyloxybenzaldehyde (1.73 g, yield 49.1%) was isolated.

[0044] 3-Hydroxy-4-propargyloxybenzaldehyde (1.70g, 10.0mmol), potassium carbonate (2.76g, 20.0mmol) was st...

Embodiment 3

[0048] B-TEG 4 The synthetic route of -COOH is as follows:

[0049]

[0050] The synthesis method is as follows:

[0051] At 0°C, a solution of p-toluenesulfonyl chloride (20.97g, 110.0mmol) in tetrahydrofuran (100mL) was slowly added dropwise to triethylene glycol monomethyl ether (16.42g, 100.0mmol) and triethylamine (22.26g, 220.0mmol) ) in dichloromethane (300mL) solution, then stirred at room temperature for 14 hours, filtered, the filtrate was washed with distilled water (150mL; 1 time), saturated ammonium chloride solution (150mL×3 times), and the organic layer was washed with anhydrous sulfuric acid After drying over sodium, the solvent was removed by rotary evaporation, and the column was separated with petroleum ether and ethyl acetate (V:V=10:1) as eluents to obtain Ts-TEG (30.88 g, yield 97.0%).

[0052] 3,4-dihydroxybenzaldehyde (1.38g, 10.0mmol), potassium carbonate (K 2 CO 3 , 6.91g, 50.0mmol), potassium iodide (KI, 0.30g) were stirred in acetone (200mL) ...

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Abstract

The invention relates to a BODIPY-based high-sensitivity fluorescent probe and a synthesis method and application thereof. A structural general formula of the probe is shown as (I), wherein Trigger is stimulant triggering groups, R1 and R2 are groups for regulating and controlling fluorescent transmission wavelength of the probe and introducing organelle targeting, and R1 and R2 are defined in the description. By the probe, detection of different substrates can be realized without changing mother nucleus structure of the probe by only changing different Trigger groups. In addition, according to different needs on wavelength and targeting, the mother nucleus structure of the probe can be quickly modified. By changing R1 and R2, maximum fluorescent emission wavelength of the probe can be changed, and the probe can target mitochondrion to realize detection of active substances in the mitochondrion. The probe has good biocompatibility, thereby being applicable to detecting biological systems. Application value of the fluorescent probe in the aspect of detecting bioactive molecules and protease over-expressed in inflammatory or tumor tissue has potential social benefit and economic benefit.

Description

technical field [0001] The invention relates to a BODIPY-based highly sensitive fluorescent probe and its synthesis method and application, in particular to the synthesis of the BODIPY-based highly sensitive fluorescent probe and its application in biological analysis and imaging. These fluorescent probes have potential applications in the detection of bioactive small molecules and proteases overexpressed in tumor or inflammatory tissues. Background technique [0002] Biological metabolism consists of many parts, including biologically active small molecules (such as hydrogen peroxide, hydrogen sulfide, etc.), and biologically active macromolecules (such as protease, etc.). The occurrence of almost all diseases is accompanied by the abnormal expression of certain active substances, therefore, the detection of these active substances can be used for the diagnosis of diseases. As a powerful tool, fluorescence imaging technology has the advantages of high spatial and temporal ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C07F9/6596C09K11/06G01N21/64C12Q1/34
CPCC07F5/022C07F5/025C07F9/6596C09K11/06C12Q1/34G01N21/6486G01N2333/984
Inventor 李昌华陈浩亮
Owner NANKAI UNIV
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