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Ultrahigh-sensitivity fluorescent probe for detecting nitrogen monoxide

A fluorescent probe, nitric oxide technology, used in fluorescence/phosphorescence, luminescent materials, organic chemistry, etc., can solve problems that have not been reported yet, and achieve the effects of simple biological detection reagents, reduced light damage, and high selectivity

Inactive Publication Date: 2012-08-01
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Especially with the development of fluorescence imaging microscopy in recent years, there are few nitric oxide fluorescent probes based on naphthalimide fluorescent chromophores, and they have not been reported internationally.

Method used

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  • Ultrahigh-sensitivity fluorescent probe for detecting nitrogen monoxide
  • Ultrahigh-sensitivity fluorescent probe for detecting nitrogen monoxide
  • Ultrahigh-sensitivity fluorescent probe for detecting nitrogen monoxide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024]

[0025] a According to the equimolar ratio of 4-bromo-1,8-naphthalene anhydride and o-nitro-p-phenylenediamine, dissolve them in ethylene glycol monomethyl ether respectively, reflux at 120°C for 5 hours under stirring, and pour the reaction solution Put into ice water, suction filter to obtain light yellow solid, yield 90%, HRMS410.9855

[0026]

[0027] b Dissolve the product obtained in step a in DMSO, add an equimolar amount of propylamine, react at 120°C for 5 hours, pour the reaction solution into ice water, and filter with suction to obtain a yellow solid with a yield of 85%, HRMS 390.1325

[0028]

[0029] c, the product that b procedure obtains is dissolved in the mixed solvent of tetrahydrofuran and methanol (volume ratio is 5: 1), adds 10% Pd / C as catalyst, the H of 2.5MPa 2 , stirred at room temperature for 24 hours, after the reaction was completed, the reactant was evaporated to dryness under reduced pressure to obtain a yellow solid with a yield...

Embodiment 2

[0031]

[0032] Replace propylamine with butylamine in b operation, all the other are with example 1, productive rate 92% HRMS 374.1733

Embodiment 3

[0034]

[0035] Use N in b operation, N-dimethylaminoethylenediamine replaces propylamine, all the other are with example 1, productive rate 91%, HRMS 389.1850

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Abstract

The invention relates to an ultrahigh-sensitivity fluorescent probe for detecting nitrogen monoxide. The ultrahigh-sensitivity fluorescent probe has the structural general formula in the original text. During preparation, firstly, 4-bromine-1, 8-anhydride naphthalene and o-nitro p-phenylenediamine with equal molar weights are used as raw materials, dissolved in ethylene glycol monomethyl ether and heated for reaction to obtain light yellow solid. Secondly, the light yellow solid is dissolved in anhydrous DMSO, primary amine is added into the anhydrous DMSO, the anhydrous DMSO is heated and refluxed, and reaction liquid is filtered in a sucking manner, depressurized and dried to obtain yellow solid. The yellow solid is dissolved in mixed liquid of tetrahydrofuran and methanol, and a yellow probe is obtained under catalysis of hydrogen and catalysts. Probe molecules have fine chemical and optical stability, good solubility and biological compatibility and high nitric oxide selectivity, and are free of interference of other active oxygen, active nitrogen and the like. Laser confocal imaging experiments indicate that the probe has fine cellular permeability, has no toxic and side effects on cells and organisms, and can be used for detecting protogenetic nitrogen monoxide in a high-sensitivity manner.

Description

technical field [0001] The invention relates to a class of high-sensitivity naphthalimide fluorescent probes for detecting nitric oxide. Background technique [0002] Nitric oxide plays an important role in life sciences and is an important messenger molecule. Since the 1980s, scientists have discovered that nitric oxide molecules are produced in the life activities of organisms. Nitric oxide not only has physiological functions such as immune regulation, neurotransmission, physiological regulation of blood pressure and inhibition of platelet aggregation, but also is closely related to many diseases, including gene mutation, cancer, arteriosclerosis and other diseases. However, the amount of nitric oxide produced in organisms is small and its half-life is short. Real-time, in situ, and quantitative detection of nitric oxide will help us further understand the physiological functions of nitric oxide and help understand The causes of certain diseases and, ultimately, appropr...

Claims

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Application Information

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IPC IPC(8): C07D221/14C07F9/50C09K11/06C12Q1/02G01N21/64
Inventor 肖义于海波张玉慧张晓琳
Owner DALIAN UNIV OF TECH
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