Azine hydrazine compound containing diethylamine as well as preparation method and application thereof

A technology of diethylamine and compounds, which is applied in the field of azinehydrazine compounds and their preparation, can solve problems such as limited application and limited solubility, and achieve the goals of increasing Stokes shift, preventing self-absorption, and strong binding ability Effect

Active Publication Date: 2020-11-17
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the solubility of such substances is limited, and they will form aggregates under physiological conditions, resulting in the inhibition of their luminescence and the generation of active oxygen, which limits their further application in the integration of microbial diagnosis and treatment.

Method used

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  • Azine hydrazine compound containing diethylamine as well as preparation method and application thereof
  • Azine hydrazine compound containing diethylamine as well as preparation method and application thereof
  • Azine hydrazine compound containing diethylamine as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076] According to the following synthetic route, specifically synthesize the following compounds:

[0077]

[0078] (1) Synthesis of compound 2

[0079] A mixture of compound 1 (2 mmol) and excess hydrazine hydrate was stirred under reflux for 4 hours. After the reaction was completed, the solvent and the remaining hydrazine hydrate were removed by rotary evaporation to obtain compound 2 as a transparent oil with a yield of 100%.

[0080] (2) Synthesis of compound DPNAP

[0081] Compound 2 (1 mmol) and Compound 3 (1.5 mmol) were stirred under reflux for 4 hours. After the reaction was completed, it was separated with a chromatographic silica gel column to obtain a yellow solid compound DPNAP (an azine hydrazine compound containing diethylamine) with a yield of 81.2%.

[0082] figure 1 The hydrogen spectrum of DPNAP proves the correctness of its structure.

[0083] figure 2 for DPNAP in H 2 Normalized UV absorption spectrum and fluorescence emission spectrum in O / T...

Embodiment 2

[0087] Embodiment 2: compound is used for identifying and killing bacteria in embodiment 1

[0088] (1) Bacteria Imaging Experiment

[0089] a. Bacteria (Escherichia coli, Staphylococcus aureus, Bacillus subtilis, Enterococcus faecalis, Pseudomonas aeruginosa, Candida albicans, Saccharomyces cerevisiae) were inoculated in 5 mL of culture medium, and cultured at 37° C. for 12 hours. Afterwards, the bacterial classification was centrifuged at 7100 rpm for 1 minute, while washing three times with phosphate buffered saline (PBS, 10 mM, pH=7.4), the supernatant was discarded, and the remaining bacterial classification was suspended in PBS, and then diluted at 600 nm to 1.0 optical density (OD 600 = 1.0). For mixed bacteria samples, Candida albicans, Escherichia coli and Staphylococcus aureus were mixed together.

[0090] b. The strains were co-stained with 5 μM DPNAP in PBS buffer solution at 37°C for 20 minutes, and then centrifuged at 7100 rpm for 1 minute. The stained strains...

Embodiment 3

[0110] According to the following synthetic route, specifically synthesize the following compounds:

[0111]

[0112] (1) Synthesis of Compound 5

[0113] A mixture of compound 4 (2 mmol) and excess hydrazine hydrate was stirred at reflux for 4 hours. After the reaction was completed, the solvent and remaining hydrazine hydrate were removed by rotary evaporation to obtain compound 5 with a yield of 100%.

[0114] (2) Synthesis of compound DO-DPAS

[0115] Compound 5 (1 mmol) and compound 3 (1.5 mmol) were stirred under reflux for 4 hours. After the reaction was completed, it was separated with a chromatographic silica gel column to obtain a yellow solid compound DO-DPAS with a yield of 75%.

[0116] Figure 16 It is the hydrogen spectrum of DO-DPAS.

[0117] Figure 17 for DO-DPAS in H 2 Normalized UV absorption and fluorescence emission spectra in O / THF (99:1, v / v) solution. [DO-DPAS] = 10 μM; λ ex = 401 nm. Depend on Figure 17 It can be seen that the maximum e...

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Abstract

The invention discloses an azine hydrazine compound containing diethylamine as well as a preparation method and application thereof. The method comprises the following steps: carrying out a heating reaction on a diphenyl hydrazine derivative and diethylamine-containing aryl in a solvent, and separating and purifying the reaction product to obtain the diethylamine-containing azine hydrazine compound. The invention further discloses application of the compound, the fluorescence intensity of the azine hydrazine compound is adjusted by adjusting the strength of interaction between the azine hydrazine compound and microorganisms, and fungus recognition and selective antibiosis are achieved. The azine hydrazine compound containing diethylamine has remarkable capability of generating active oxygen due to aggregation-induced emission (AIE) property, shows selective bacterial fluorescence staining capability and antibacterial activity, and has a good application prospect.

Description

technical field [0001] The invention belongs to the field of analysis and detection materials, and in particular relates to a diethylamine-containing azine hydrazine compound and a preparation method and application thereof. Background technique [0002] Human beings have suffered from infectious diseases caused by various pathogenic microorganisms (such as bacteria, fungi, viruses and parasites) since ancient times. For many years, antibiotics have been widely used as the most effective drugs to control epidemic diseases, but due to the misuse and abuse of antibiotics in medical and health, industrial and agricultural production and other fields (antibiotics are used in agriculture and animal husbandry to help livestock grow), evolved Antimicrobial-resistant pathogenic bacteria have caused hundreds of thousands of deaths in developed countries every year. Relevant data from 129 member states collected by the World Health Organization (WHO) show that antibiotic resistance h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C251/88C09K11/06C12Q1/18G01N21/64
CPCC07C251/88C09K11/06G01N21/6428C12Q1/18G01N2021/6432C09K2211/1007Y02A50/30
Inventor 唐本忠王志明胡蓉周凡崔娜邓棋云张可心印平安
Owner SOUTH CHINA UNIV OF TECH
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