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Tricyclic 2-amino pyridinium salt fluorescent probe as well as preparation method and application of fluorescent probe

An aminopyridinium salt, fluorescent probe technology, applied in the field of biomedical materials, can solve the problems of reducing sensitivity, aggregation-induced luminescence quenching, reducing signal-to-noise ratio, etc.

Active Publication Date: 2020-11-20
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to its large π-conjugated system, traditional fluorescent materials have the problem of aggregation-induced luminescence quenching (ACQ) in the aggregated state; their high background fluorescence will also reduce the signal-to-noise ratio in the detection and diagnosis process. will greatly reduce the sensitivity of its detection

Method used

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  • Tricyclic 2-amino pyridinium salt fluorescent probe as well as preparation method and application of fluorescent probe
  • Tricyclic 2-amino pyridinium salt fluorescent probe as well as preparation method and application of fluorescent probe
  • Tricyclic 2-amino pyridinium salt fluorescent probe as well as preparation method and application of fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078] Embodiment 1 Preparation of a fluorescent probe (BMTAPC-7)

[0079]

[0080] The synthetic route is as follows:

[0081]

[0082] 4-bromobenzoyl chloride (10mmol, 2.19g), 4-methoxyphenylacetylene (10mmol, 1.32g), PdCl 2 (PPh 3 ) 2 (0.2mmol, 144mg) and cuprous iodide (0.4mmol, 76mg) were added to a 250mL two-necked round-bottomed flask, then evacuated with a pump, replaced with nitrogen three times for 3 times; then added dry dichloromethane (100mL) . Triethylamine (11 mmol, 1.5 mL); the reaction was stirred at room temperature for 5 h (reaction progress was monitored by TLC). After the substrate reaction is complete, slowly add anhydrous AlCl to the reaction system 3 (1mmol, 133mg) and DBU (30mmol, 4.5mL), the reaction mixed solution was stirred at room temperature for 2h (TLC monitoring until the reaction was complete), the mixed reaction solution was filtered to remove the catalyst, the filtrate was concentrated, acidified with 20mL of 1M hydrochloric acid, ...

Embodiment 2

[0084] Embodiment 2 Preparation of a fluorescent probe (BMTAPC-5)

[0085]

[0086] The synthetic route is as follows:

[0087]

[0088] 4-bromobenzoyl chloride (10mmol, 2.19g), 4-methoxyphenylacetylene (10mmol, 1.32g), PdCl 2 (PPh 3 ) 2 (0.2mmol, 144mg) and cuprous iodide (0.4mmol, 76mg) were added to a 250mL two-necked round-bottomed flask, then evacuated with a pump, replaced with nitrogen three times for 3 times; then added dry dichloromethane (100mL) , triethylamine (11mmol, 1.5mL), the reaction was stirred at room temperature for 5h (reaction progress was monitored by TLC), and after the substrate had completely reacted, anhydrous AlCl was slowly added to the reaction system 3 (1 mmol, 133 mg) and DBN (30 mmol, 4.5 mL). The reaction mixed solution was stirred at room temperature for 2 h (TLC monitoring until the reaction was complete), the mixed reaction solution was filtered to remove the catalyst, the filtrate was concentrated, acidified with 20 mL of 1M hydroc...

Embodiment 3

[0090] Embodiment 3 Preparation of a fluorescent probe (BMTAP-7)

[0091]

[0092] The synthetic route is as follows:

[0093]

[0094] The solid BMTAPC-7 (1mmol, 485mg) synthesized in Example 1 was dissolved in acetone, an aqueous solution of potassium hexafluorophosphate (2mmol, 368mg) was added, stirred for 2h, the mixture was added with water and then filtered, and the filtered solid was washed with water to remove inorganic salts , dried to give 535 mg of yellow solid BMTAP-7 in 90% yield.

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Abstract

The invention belongs to the technical field of fluorescent probes, and discloses a tricyclic 2-amino pyridinium salt fluorescent probe as well as a preparation method and application of the fluorescent probe. The structure of the tricyclic 2-amino pyridinium fluorescent probe is shown as a formula I, wherein R1 and R2 are independently electron donating groups of aryl, heteroaryl, C1-18 alkyl, C3-8 naphthenic base or aromatic ring derivatives; X is a monovalent anion; m is any integer from 0 to 2; and n is any integer of 0 or 1. The invention also discloses a preparation method of the fluorescent probe. The fluorescent probe provided by the invention has aggregation-induced emission properties, can realize rapid staining recognition of microorganisms, and shows the characteristics of specificity, high efficiency and sensitivity. The fluorescent probe provided by the invention has an excellent antibacterial effect. The fluorescent probe provided by the invention is used for preparing reagents for specific dyeing of mitochondria and dyeing of microorganisms with negative charges on the surface, and is also used for preparing reagents and antibacterial agents for distinguishing deadand living states of microorganisms. .

Description

technical field [0001] The invention belongs to the field of biomedical materials, and in particular relates to a fluorescent probe of a tricyclic 2-aminopyridine salt, a preparation method thereof, and an application in microbial marker recognition and bacteriostasis. Background technique [0002] Under normal conditions, microorganisms and humans are interdependent to maintain the balance of physiological metabolism; once the balance is broken, it is easy to cause diseases. Bacterial infection can cause a variety of diseases and seriously threaten human health. Diagnosis of the bacteria is the first step in the course of treatment. At present, the Gram staining method is mainly used, which is complicated to operate and cannot realize in situ monitoring of live bacteria. At the same time, in the process of treatment, due to the abuse of antibiotics, the emergence of drug-resistant bacteria makes the treatment more difficult. Therefore, it is very important to develop acc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/16C09K11/06A61P31/04A61K31/55A61K31/519G01N21/64
CPCC07D471/16C09K11/06A61P31/04G01N21/6428C09K2211/1007C09K2211/1044G01N2021/6439
Inventor 唐本忠秦安军王柄楠胡蓉蓉赵祖金王志明
Owner SOUTH CHINA UNIV OF TECH
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