Fluorescent probe DCCO and preparation method and application thereof

A technology of fluorescent probes and stock solutions, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of complex operation, low sensitivity, and inability to apply HClO/ClO- detection, etc., to achieve good selectivity, The effect of high sensitivity and short response time

Active Publication Date: 2019-09-24
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods have low sensitivity, complicated operation, and more importantly, cannot be applied to HClO / ClO in vivo - detection

Method used

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  • Fluorescent probe DCCO and preparation method and application thereof
  • Fluorescent probe DCCO and preparation method and application thereof
  • Fluorescent probe DCCO and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The preparation of embodiment 1 fluorescent probe DCCO

[0029] (1) 3-acetyl-7-(diethylamino)-2H-pyran-2-one (0.777g, 3mmol), 9-ethyl-9H-carbazole-3-formaldehyde (0.669g, 3mmol), dissolved in 15mL of ethanol / acetonitrile (1 / 1, V / V) mixed solution, piperidine (0.75mL, 7.5mmol) was added dropwise, heated to reflux for 30 hours, the reaction solution turned from orange to red, TLC Tracking Response (V 乙酸乙酯 :V 石油醚 =1:3);

[0030] (2) After the reaction is over, the solvent is removed under reduced pressure, and the gradient elution method is used for column chromatography separation, first eluted with ethyl acetate / petroleum ether (1 / 3, V / V), and then ethyl acetate / petroleum ether (1 / 2, V / V) elutes, obtains 0.699g crude product;

[0031] (3) The crude product was dissolved in ether, filtered, and dried to obtain 0.349 g of an orange-yellow pure product with a yield of 25%.

[0032] For fluorescent probes 1 H NMR characterization, the results are as follows:

[0033] ...

Embodiment 2

[0035] Embodiment 2 fluorescent probe DCCO with ClO - Varying UV Absorption Spectrum

[0036] Add 10.0 μL of fluorescent probe stock solution to 2.0 mL of water / DMSO (1 / 1, v / v) system for ClO - UV titration experiment, and record its UV absorption spectrum ( figure 1 ). With ClO - With the increase of the amount, the ultraviolet absorption at 290nm, 321nm and 355nm all increased, and the ultraviolet absorption at 480nm decreased.

Embodiment 3

[0037] Embodiment 3 fluorescent probe DCCO with ClO - Fluorescence titration plot of change

[0038] Add 10.0 μL fluorescent probe stock solution to 2.0 mL water / DMSO (1 / 1, v / v) system for ClO -Fluorescence titration experiment, detected on a spectrofluorometer, with ClO - With the increase of , the fluorescence intensity at 570nm gradually weakened, and a new peak appeared at 420nm and gradually increased ( figure 2 ). Instrument parameters: the slit widths of the excitation wavelength and emission wavelength are 5.0nm and 5.0nm respectively, the voltage is 600V, and the maximum excitation wavelength of the fluorescent probe solution is: λ ex 335nm and a maximum emission wavelength of λ em 570nm. Fluorescence ratio I 420nm / I 570nm Plotting the graph for the ordinate gives ClO - Concentration working curve, the linear regression equation is I 420nm / I 570nm =0.033*[NaClO]-1.586, the unit of NaClO concentration is 10 -6 mol / L; the linear correlation coefficient is...

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Abstract

The invention provides a fluorescent probe DCCO and a preparation method and application thereof. The fluorescent probe is 7-(diethylamino)-3-(E)-3-(9-ethyl-9H-carbazole-3-base)acryloyl-2H-pyran-2-ketone. The preparation method of the fluorescent probe DCCO comprises the steps that 3-acetyl-7-(diethylamino)-2H-pyran-2-ketone and 9-ethyl-9H-carbazole-3-formaldehyde amine are dissolved in an ethyl alcohol / acetonitrile (1 / 1, V / V) mixed solution in an equimolar ratio, piperidine is dripped, heating reflux is carried out, and the solution is changed from saffron yellow to red; decompression is carried out to remove a solvent, column chromatography isolation is carried out through a gradient elution method, and a crude product of the fluorescent probe is obtained; the crude product of the fluorescent probe is dissolved, filtered and dried to obtain a pure product. The detection of ClO<-> by the fluorescent probe is of a ratio type, the high sensitivity and good selectivity and stability are shown, and the fluorescent probe has the advantages that the detection process is simple, convenient and rapid, and detection results are accurate. The fluorescent probe DCCO can be applied in the detection of ClO<-> of biological samples.

Description

technical field [0001] The invention relates to an organic small molecule fluorescent probe, specifically belongs to a fluorescent probe DCCO and a preparation method thereof, and the probe is applied to ClO in biological samples - detection. Background technique [0002] For more than 100 years, ClO - As an effective drug against a variety of microorganisms, it is used as a clinical general disinfectant. In animals and humans, ClO - Also considered a key microbicide during the immune response, corresponding to the digestion process of bacteria engulfed by neutrophils. However, under inflammatory conditions, the excess HClO produced may trigger or exacerbate a variety of diseases, including Alzheimer's disease, cardiovascular disease, atherosclerosis, inflammatory bowel disease, myocardial infarction, organ transplant rejection, and even cancer. Therefore, there is an urgent need to develop a method for detecting ClO in organisms - fast and effective tool. [0003] Cur...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D405/06G01N21/64A61K49/00
CPCA61K49/0021C07D405/06C09K11/06C09K2211/1029C09K2211/1088G01N21/6428G01N21/643
Inventor 钞建宾段月香张永斌
Owner SHANXI UNIV
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