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Long-wavelength fluorescence probe, and preparation method and application thereof

A fluorescent probe, long-wavelength technology, applied in the field of fluorescent probes, can solve problems such as the influence of fluorescence intensity, and achieve the effects of less biological damage, simple preparation method and good selectivity

Inactive Publication Date: 2015-06-10
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, commercial fluorescein and rhodamine sulfhydryl fluorescent reagents have been developed and utilized, but the fluorescence intensity of these fluorescent reagents is easily affected by the environment (such as pH and temperature), and most of their excitation and emission wavelengths are in the ultraviolet-visible region. Therefore, the application in biological

Method used

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  • Long-wavelength fluorescence probe, and preparation method and application thereof
  • Long-wavelength fluorescence probe, and preparation method and application thereof
  • Long-wavelength fluorescence probe, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Dissolve 1,3,5,7-tetramethyl-8-phenyl-(2'-nitro)boron difluoride dimethylpyrrole (0.65 mmol) in benzene (15 mL), then add benzaldehyde in sequence (1.30mmol), piperidine (0.52mL) and glacial acetic acid (0.39mL), refluxed at 75°C for 30h with an oil-water separator, distilled off the solvent under reduced pressure, and purified by column chromatography with dichloromethane as eluent to obtain 1,7-Dimethyl-3,5-distyryl-8-phenyl-(2'-nitro)-borondifluoride dipyrromethane (276.5 mg, 78% yield), the intermediate Product 1: Dissolve intermediate product 1 (276.5mg, 0.50mmol) in 47mL of glacial acetic acid, add 6.5g of zinc powder, stir at room temperature for 80min, filter with suction to obtain the filtrate, distill off the solvent under reduced pressure, rinse with dichloromethane The solution was purified by column chromatography to obtain 1,7-dimethyl-3,5-distyryl-8-phenyl-(2'-amino)-boron difluoride dipyrromethane (194.3 mg, yield 75%), namely the intermediate product 2...

Embodiment 2

[0036]Dissolve 1,3,5,7-tetramethyl-8-phenyl-(2'-nitro)boron difluoride dimethylpyrrole (1.56mmol) in 20mL of benzene, then add benzaldehyde (4.68 mmol), piperidine (1.3mL) and glacial acetic acid (1.1mL), heated to reflux at 80°C for 24 hours with an oil-water separator device, distilled off the solvent under reduced pressure, and purified by column chromatography with dichloromethane as eluent to obtain Blue solid powder compound 2,1,7-dimethyl-3,5-distyryl-8-phenyl-(2'-nitro)-borondifluoride dipyrromethane (680.4 mg, yield 80%), namely intermediate product 1; intermediate product 1 (680.4 mg, 1.24 mmol) was dissolved in 100 mL of glacial acetic acid, zinc powder (17.5 g) was added, stirred at room temperature for 90 min, and the filtrate was obtained by suction filtration, which was distilled off under reduced pressure Solvent, purified by column chromatography with dichloromethane as eluent to obtain blue solid powder compound 1,7-dimethyl-3,5-distyryl-8-phenyl-(2'-amino) ...

Embodiment 3

[0038] Dissolve 1,3,5,7-tetramethyl-8-phenyl-(2'-nitro)boron difluoride dimethylpyrrole (1.56mmol) in 20mL of benzene, then add benzaldehyde (6.25 mmol), piperidine (1.4mL) and glacial acetic acid (1.25mL), heated to reflux at 85°C for 28 hours with an oil-water separator, distilled off the solvent under reduced pressure, and purified by column chromatography with dichloromethane as eluent to obtain Blue solid powder compound 2,1,7-dimethyl-3,5-distyryl-8-phenyl-(2'-nitro)-borondifluoride dipyrromethane (671.9 mg, yield 79%), that is, intermediate product 1; intermediate product 1 (671.9 mg, 1.22 mmol) was dissolved in 104 mL of glacial acetic acid, zinc powder (18.3 g) was added, stirred at room temperature for 84 min, and the filtrate was obtained by suction filtration, which was distilled off under reduced pressure Solvent, using dichloromethane as the eluent for column chromatography purification, to obtain blue solid powder compound 3,1,7-dimethyl-3,5-distyryl-8-phenyl-(2...

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Abstract

The invention discloses a long-wavelength fluorescence probe, and a preparation method and application thereof. The preparation method comprises the following steps: reacting 1,3,5,7-tetramethyl-8-phenyl-(2'-nitro)-boron difluoride-dimethyl pyrrole and benzaldehyde to generate a conjugated system with a larger 3,5-distyryl group, reducing -NO2 into -NH2 with zinc powder, carrying out addition reaction with maleic anhydride, and reacting with acetic anhydride to obtain the long-wavelength fluorescence probe 1,7-dimethyl-3,5-distyryl-8-phenyl-(2'-maleimido)-boron difluoride dipyrromethene. The preparation method is simple; the prepared long wavelength fluorescence probe has the advantages of small influence by environmental pH value, favorable selectivity for sulfhydryl compounds, and high sensitivity; the autofluorescence intensity of the fluorescence probe is very weak, but can be enhanced after reaction with sulfhydryl group, and thus, the fluorescence probe can be used for detecting sulfhydryl compounds; and the fluorescence probe can generate small damage to organisms, and thus, has wide application prospects in the fields of biological tissues, cell fluorescence imaging and the like.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes, and relates to a long-wavelength fluorescent probe for detecting sulfhydryl compounds, a preparation method and application thereof. Background technique [0002] Sulfhydryl compounds are important components of various proteins and simple small molecules in organisms, and play an important role in the metabolic activities of organisms. Studies have shown that many intracellular and extracellular redox reactions, metal transfer reactions, carbon dioxide fixation, and reactions involving coenzyme A are all related to sulfhydryl compounds to a certain extent. Too much or too little mercapto compounds in the body can cause some diseases, such as liver damage, Alzheimer's disease, coronary heart disease and stroke. Therefore, the determination of sulfhydryl compounds is of great significance to the understanding and treatment of these diseases. [0003] Fluorescent probes have been widel...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07F5/02G01N21/64
Inventor 王红张华山张李云郭小峰
Owner WUHAN UNIV
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