Methylene violet derivative fluorescent probe as well as synthesis method and application thereof

A methylene violet and fluorescent probe technology, applied in the field of fluorescent sensing materials, can solve the problems of surrounding tissue damage, inability to directly act on the target tissue, and partial treatment effect, and achieve good anti-tumor ability, fast speed, and water solubility Good results

Active Publication Date: 2021-03-12
HUBEI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the therapeutic effect is quite partial and requires very high selectivity. Without a positioning group, it cannot directly act on the target tissue and has harmful effects on the surrounding tissue.

Method used

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  • Methylene violet derivative fluorescent probe as well as synthesis method and application thereof
  • Methylene violet derivative fluorescent probe as well as synthesis method and application thereof
  • Methylene violet derivative fluorescent probe as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] A method for preparing a fluorescent probe of a methylene violet derivative is provided, and the reaction formula is as follows:

[0054]

[0055] Include the following steps:

[0056] (1) Dissolve 4-fluoronitrobenzene (4g, 28mmol), potassium carbonate (7.84g, 54mmol) and piperazine (3.6g, 42mmol) in DMSO (30mL), stir at 70°C for 5h, then add appropriate amount of Ice water, a large number of yellow solids precipitated, suction filtered to obtain yellow solid D.

[0057] (2) The above-mentioned compound D (5g, 16mmol), iron powder (1.8g, 32mmol) and ammonium chloride (2.6g, 48mmol) were dissolved in ethanol (100mL), refluxed at 90°C, monitored by TLC until the raw material point disappeared, After the solution is cooled, add saturated sodium bicarbonate solution, stir well and filter. Extracted with ethyl acetate, evaporated to dryness under reduced pressure, and separated by column chromatography to obtain brown oily liquid E.

[0058] (3) The above compound E (1...

Embodiment 2

[0066] A method for preparing a fluorescent probe of a methylene violet derivative is provided, and the reaction formula is as follows:

[0067]

[0068] Include the following steps:

[0069] (1) Methylene violet 3RAX (1 g, 2.6 mmol), chloroacetyl chloride (0.33, 2.9 mmol) and triethylamine (provided with basic conditions) were all dissolved in dichloromethane (25 mL), stirred at room temperature for 8 h, Evaporate to dryness under reduced pressure, and separate by column chromatography to obtain a purple solid A 1 .

[0070] (2) the above compound A 1 (1g, 2mmol), piperazine (0.38g, 4mmol) and potassium carbonate (weak base conditions) (1.2g, 9mmol) were all dissolved in acetonitrile (30mL), stirred at room temperature for 2h, evaporated to dryness under reduced pressure, ethyl acetate Ester extraction, separation by column chromatography, to obtain a red solid B 1 .

[0071] (3) the above compound B 1 (1g, 2mmol), NBD-Cl (0.6g, 3mmol) and triethylamine (provided wit...

Embodiment 3

[0074] A method for preparing a fluorescent probe of a methylene violet derivative is provided, and the reaction formula is as follows:

[0075]

[0076] (1) Add methylene violet 3RAX (1g, 2.6mmol) to concentrated hydrochloric acid and stir for 3h at room temperature, then add 1-phenylpiperazine (0.64g, 4mmol) to the concentrated hydrochloric acid solution of methylene violet , After continuing to stir for 4h, suction filtration gave blue solid C.

[0077] (2) The above-mentioned compound C (1g, 2mmol), NBD-Cl (0.54g, 3mmol) and triethylamine (provided with basic conditions) were all dissolved in dichloromethane (20mL), stirred at 40°C for 15h, and then Evaporate to dryness under pressure and separate by column chromatography to obtain a blue-green solid, which is the fluorescent probe of the methylene violet derivative, which is denoted as 3RAX-N-NBD-3 probe.

[0078] different concentrations of Na 2 The linear curve (R=0.9908) obtained after the interaction of S with th...

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Abstract

The invention discloses a methylene violet derivative fluorescent probe as well as a synthesis method and application thereof. The fluorescent probe is connected with an NBD group through piperazine on the basis of a cationic main structure of methylene violet. The preparation method comprises the following steps: directly reacting methylene violet 3RAX with piperazine, or firstly reacting with X-R5-X and then reacting with piperazine, and finally introducing an NBD group to a piperazine group to obtain the target fluorescent probe; or reacting 4-fluoronitrobenzene, piperazine and aniline to obtain a cationic main structure of methylene violet, and finally introducing an NBD group to a piperazine group to obtain the target fluorescent probe. The fluorescent probe is good in water solubility, can be used for sulfur ion detection, is high in detection sensitivity and low in detection limit, and can also be used as a tumor photodynamic therapy probe to quickly release singlet oxygen for tumor photodynamic therapy; synthesis is simple, conditions are mild, and cost is low.

Description

technical field [0001] The invention relates to the technical field of fluorescent sensing materials, in particular to a methylene violet derivative fluorescent probe and its synthesis method and application. Background technique [0002] Sulfide ions exist in some industrial wastewater and domestic sewage, and protonation will produce highly toxic hydrogen sulfide, which is a recognized environmental pollutant; protonation of sulfide ions in organisms forms hydrogen sulfide gas. With the pair S 2- Through in-depth research, it is found that low-concentration protonated sulfide ions are the third important endogenous gas signal molecules that play physiological roles, and are closely related to many diseases. This gas molecule is responsible for important physiological and pathological functions in the cardiovascular and nervous systems. Regulatory effect. Studies have shown that levels of hydrogen sulfide are associated with a variety of diseases, including Alzheimer's di...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/12C09K11/06G01N21/64A61K41/00
CPCC07D413/12C09K11/06G01N21/643A61K41/0057C09K2211/1044C09K2211/1048
Inventor 王凯贾芳宋世昊赵芳潘洁赵一玫姜军叶文静
Owner HUBEI UNIV
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