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Nitric oxide probe based on fluorescent double-response mechanism and synthesis and application thereof

A nitric oxide and fluorescent probe technology, applied in the field of organic photochemistry, can solve the problems of background fluorescence interference, low detection sensitivity, semi-quantitative and quantitative detection of few cells, and achieve short response time, high sensitivity and good application foreground effect

Inactive Publication Date: 2017-02-22
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Existing nitric oxide (NO) probes are based on the structure of ortho-diamines, but usually the NO probes based on ortho-diamines are often analyzed and detected by directly utilizing the changes in the fluorescence spectrum emission intensity of the probe molecule itself, so that The method will be limited by the background fluorescence interference of the probe itself, resulting in low detection sensitivity
In addition, traditional NO probes based on o-phenylenediamine substituents are rarely used for semi-quantitative and quantitative detection in cell imaging due to their own background interference.

Method used

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  • Nitric oxide probe based on fluorescent double-response mechanism and synthesis and application thereof
  • Nitric oxide probe based on fluorescent double-response mechanism and synthesis and application thereof
  • Nitric oxide probe based on fluorescent double-response mechanism and synthesis and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] The molecular structure of the probe molecular material A-1 prepared in this example is:

[0053]

[0054] The present embodiment 1 is prepared by the preparation method (1), and the specific steps are:

[0055] i) In a two-neck flask (100mL), dissolve 4,7-dibromo-2,1,3-benzothiadiazole (2.01g, 6.84mmol), 2-thiopheneboronic acid (1.42g, 11mmol) in 20mL toluene 15 mL of 2M potassium carbonate solution was injected into the mixture, and the gas was exchanged three times. Under nitrogen protection, tetrakis(triphenylphosphine)palladium (150 mg, 0.14 mmol) was added, heated to 75° C., and reacted for 2-8 hours. Naturally cooled to room temperature, extracted with dichloromethane, dried, concentrated, and separated by column chromatography to obtain 1.73 g of red crystal 4,7-dithiophene-2,1,3-benzothiadiazole with a yield of 84.3%. 1 H NMR (400MHz, CDCl 3 )δ8.12(dd, J=3.7,1.1Hz,2H),7.88(s,2H),7.46(dd,J=5.1,1.1Hz,2H),7.24–7.20(m,2H). 13 C NMR (101MHz, CDCl 3 ) δ152.61,...

Embodiment 2

[0060] The molecular structure of the probe molecular material B-1 prepared in this example is:

[0061]

[0062] The present embodiment 2 is prepared by the preparation method (1), and the specific steps are:

[0063] i) The preparation process of 4,7-dithiophene-2,1,3-benzothiadiazole is the same as step i) of Example 1.

[0064] ii) In a two-necked flask (250ml), 1-bromo-2-(2-(2-methoxyethoxy)ethoxy)ethane (7.3g, 27.4mmol), dibromofluorene (2.9g , 12mmol), potassium iodide (200mg, 1.2mmol) was dissolved in DMSO (100ml) and 50% (w / w) NaOH aqueous solution (30ml). The reaction mixture was at 60. Inversely stirred for 6h. Extracted with dichloromethane, dried, concentrated, and separated by column chromatography to obtain light yellow liquid 9,9-bis(3,3'-2-(2-(2-methoxyethoxy)ethoxy)ethane) - 4.9 g of 2-bromofluorene, yield 79.1%. 1 H NMR (400MHz, CDCl 3)δ7.65(dd, J=5.6,3.0Hz,1H),7.56–7.52(m,2H),7.46(dd,J=8.0,1.8Hz,1H),7.38(d,J=2.6Hz,1H ), 7.33(dd, J=6.2, 2.8Hz, 2H),...

Embodiment 3

[0068] The molecular structure of the probe molecular material C-1 prepared in this example is:

[0069]

[0070] The present embodiment 3 is prepared by the preparation method (2), and the specific steps are:

[0071] i) In a two-necked bottle (100mL), 4,7-dibromo-2,1,3-benzothiadiazole (2.01g-3.05, 6.84-10mmol), trimethylsilylacetylene (0.67g-1.0g , 15-22.5mmol) was dissolved in 20-40mL tetrahydrofuran, and 15-30mL triethylamine was injected. The gas was exchanged three times, and under the protection of nitrogen, tetrakis(triphenylphosphine)palladium (50-150 mg, 0.05-0.14 mmol) was added, and the mixture was reacted at 50-80° C. for 4-24 h. Naturally cooled to room temperature, extracted with dichloromethane, dried, concentrated, and separated by column chromatography to obtain yellow-green crystal 4,7-ditrimethylsilylethynyl-2,1,3-benzothiadiazole, yield 77- 84.3%. 1 H NMR (400MHz, CDCl 3 )δ8.22(dd,J=3.7,1.1Hz,2H),0.14(m,18H).

[0072] ii) In a two-neck flask (150m...

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Abstract

The invention discloses a molecular design and preparation method of a nitric oxide fluorescent probe based on a double-response mechanism. The structure of the nitric oxide fluorescent probe can be represented by a general formula (I) (please see the formula in the description), wherein Spacer represents a single bond or acetylene bond or thiophene or substituted aryl unit, Ar represents one of an aryl group, a substituted aryl group, a heterocyclic aryl group and substituted aryl amine, and the substituted group can be one of a hydrophilic ether chain, a sulfonic acid group, quaternary ammonium salt and the like. The key steps of synthesis of the probe molecule can be achieved through a Suzuki coupling reaction or a C-H activation coupling reaction and the like. The probe molecule has the advantages of being high in sensitivity, good in selectivity, short in response time, good in membrane permeability, low in background noise, capable of achieving direct observation and fluorescence-ultraviolet-visible spectrum dual-band response and the like, is a brand-new sensing detection platform and has a good application prospect.

Description

technical field [0001] The invention belongs to the technical field of organic photochemistry, and in particular relates to a class of probe molecular materials based on a fluorescence "double response" mechanism, specifically a class of push- An electron-pulling conjugated semiconductor organic molecular material, which realizes the detection of dual signal responses to nitric oxide molecules and the application of fluorescence imaging. Background technique [0002] Sensing technology is the cutting-edge technology of modern science and technology. Many countries have listed sensing technology as equally important as communication technology and computer technology, becoming one of the three pillars of information technology. The so-called sensing technology is a series of technical measures taken by people to qualitatively understand and quantitatively grasp the information contained in the measured object, and the sensor is the device or device that completes the correspo...

Claims

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Application Information

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IPC IPC(8): C07D333/24C07D333/20C07D209/86C07D519/00C09K11/06G01N21/64
CPCG01N21/6486C09K11/06C07D209/86C07D333/20C07D333/24C07D519/00C09K2211/1092C09K2211/1029
Inventor 黄维李清赵保敏李兆宁董晓臣
Owner NANJING UNIV OF TECH
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