Pyrenes fluorescent probe and preparation method and application thereof

A fluorescent probe and pyrene technology, applied in the field of fluorescent probes, can solve the problems of loss of consciousness or even death, environmental pollution, human vomiting, etc., and achieve the effects of simple preparation method, simple detection method, and good cell membrane permeability.

Inactive Publication Date: 2017-05-17
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, cyanide is highly toxic and can cause vomiting, convulsions, loss o

Method used

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  • Pyrenes fluorescent probe and preparation method and application thereof
  • Pyrenes fluorescent probe and preparation method and application thereof
  • Pyrenes fluorescent probe and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] The preparation of embodiment 1 pyrene fluorescent probe, the steps are as follows:

[0054] Take 0.61g (2.5mmol) of acetylpyrene and dissolve it in 60mL of absolute ethanol in a 250mL two-necked flask (it can be heated appropriately to accelerate the dissolution), and then add 0.63g (3.5mmol) of 2,6 -dichloropyridine-3-carbaldehyde solution, then add 3 mL of 10% aqueous sodium hydroxide solution, and stir with a magnetic stirrer at room temperature for 20 h. After the reaction was completed, it was filtered, spotted on a plate to confirm the purity of the product, dried naturally for 3 hours, and then dried in a vacuum oven for 2 hours to obtain 0.89 g of an orange-yellow product with a yield of 88.6%.

[0055] The fluorescent probe was characterized by NMR, and the results are as follows:

[0056] 1 H NMR (600MHz, DMSO-d 6 )δ / ppm: 8.803~8.788(d, 1H, J=9.0Hz), 8.728~8.714(d, 1H, J=8.4Hz), 8.636~8.623(d, 1H, J=7.8Hz), 8.467~8.429 (m, 3H), 8.396~8.380(d, 2H, J=9.6Hz)...

Embodiment 2

[0057] The H of embodiment 2 pyrene fluorescent probes + Titration fluorescence plot

[0058] Add 30 μL pyrene-based fluorescent probe stock solution to 2 ml distilled water for H + Fluorescence titration experiments were detected on a fluorescence spectrophotometer. With the addition of the sample to be tested, the fluorescence intensity at 460nm weakens, and the fluorescence at 420nm increases gradually. Instrument parameters: the slit widths of the excitation wavelength and emission wavelength are 5.0nm and 5.0nm respectively, and the maximum excitation wavelength of the fluorescent probe solution is: λ ex 365nm and maximum fluorescence emission wavelength: λ em 460nm.

Embodiment 3

[0059] Example 3 Pyrene fluorescent probe pair H + Responsive working curve

[0060] Prepare 0.01M, 0.1M, 1M H with distilled water + Solution, 2ml distilled water and 30 μ L pyrene fluorescent probe stock solution are added in the fluorescence cuvette, carry out titration experiment (pH variation range 7.30-1.95); Take pH as abscissa, relative fluorescence intensity I 420nm / I 460nm Draw a graph for the ordinate and perform Sigmoidal fitting to obtain pK a =3.76; Obtaining the best linear response range is pH 3.10-4.66 by linear fitting, and the regression equation is: I 420nm / I 460nm =3.39-0.64*pH, the linear coefficient is R 2 = 0.9819.

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Abstract

The invention provides a pyrenes fluorescent probe and a preparation method and application thereof. The preparation method of the probe comprises the following steps: dissolving acetyl pyrene and 2,6-dichloropyridine-3-formaldehyde with ethanol respectively, mixing, adding 10 percent by mass aqueous sodium hydroxide, and stirring with a magnetic stirrer at the normal temperature for 20 hours; filtering after a full reaction, determining whether a product is pure or not, and drying the product to obtain an orange-yellow solid. The probe has high sensitivity and high selectivity specific to CN<->, HSO3<-> and pH in different systems. In combination with a laser confocal scanning microscopy technology, the pyrene fluorescent probe can be applied to the detection of pH or HSO3<-> in cells, and can be applied to the detection of escherichia coli pH.

Description

technical field [0001] The invention relates to the technical field of fluorescent probes, in particular to a pyrene-based fluorescent probe and its preparation method and application. Background technique [0002] Due to the advantages of non-destructive detection, high sensitivity, strong specificity and fast response time, fluorescence spectroscopy detection technology has attracted more and more attention. Fluorescence imaging has high temporal and spatial resolution and is easy to operate, making it an important means of real-time monitoring of cells. [0003] CN - , HSO 3 - , pH plays a very important role in industrial processes, daily life and physiological processes. Sulfites are widely used in our daily life as preservatives and additives in many food, beverage and pharmaceutical products. However, when sulfite levels are abnormal in the body, it is likely to cause serious illness, including difficulty breathing, wheezing, hives, gastrointestinal distress, and...

Claims

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Application Information

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IPC IPC(8): G01N21/64
CPCG01N21/6428G01N21/6486
Inventor 钞建宾宋凯伦王会娟张永斌王娟娟
Owner SHANXI UNIV
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