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Fluorescent probe HM, and preparation method and application thereof

A fluorescent probe and stock solution technology, applied in the field of fluorescent probes, can solve the problems of complex operation, low sensitivity, and inability to use HClO/ClO-detection, etc., and achieve the effects of good selectivity, high sensitivity and short response time.

Active Publication Date: 2021-05-04
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 HM, and preparation method and application thereof
  • Fluorescent probe HM, and preparation method and application thereof
  • Fluorescent probe HM, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The preparation of embodiment 1 fluorescent probe

[0028] (1) Dissolve 7-(diethylamino)coumarin-3-carbaldehyde (0.1225g, 0.5mmol) and 1-(2-hydroxy-5-methoxyphenyl)ethanone (0.083,0.5mmol) In acetonitrile (10mL), piperidine (0.1mL, 1mmol) was added dropwise, heated to reflux for 20 hours, during which a red solid was continuously precipitated;

[0029] (2) After the reaction finishes, cool to room temperature, and a large amount of red solids are precipitated;

[0030] (3) Filtrate under reduced pressure, wash the precipitate, and dry to obtain 0.063 g of a red solid product with a yield of 32%.

[0031] For fluorescent probes 1 H NMR characterization, the results are as follows:

[0032] 1 H NMR (600MHz, DMSO-d 6 ,δ / ppm): δ11.98(s,1H),8.55(s,1H),8.07(d,J=15.4Hz,1H),7.77(d,J=15.3Hz,1H),7.52(d, J=9.0Hz, 1H), 7.44(d, J=3.0Hz, 1H), 7.21(dd, J=9.0, 3.0Hz, 1H), 6.95(d, J=9.0Hz, 1H), 6.82(dd, J=9.0,2.2Hz,1H),6.62(d,J=1.9Hz,1H),3.80(s,3H),3.50(q,J=7.0Hz,4H),1.15(t,J=7.0...

Embodiment 2

[0034] Embodiment 2 fluorescent probe HM along with ClO - Varying UV Absorption Spectrum

[0035] In 2.0mL C 2 h 5 Add 10.0 μL fluorescent probe stock solution to OH / PBS (2 / 3, v / v) system, and carry out ClO - UV titration experiment, and record its UV absorption spectrum ( figure 1 ). With ClO - With the increase of the amount, the ultraviolet absorption value at 400nm increases, and the ultraviolet absorption value at 490nm decreases.

Embodiment 3

[0036] Embodiment 3 fluorescent probe HM along with ClO - Fluorescence titration plot of change

[0037] In 2.0mL C 2 h 5 Add 10.0 μL fluorescent probe stock solution to OH / PBS (2 / 3, v / v) system for ClO -Fluorescence titration experiment, detected on a spectrofluorometer, with ClO - With the increase of , the fluorescence intensity at 605nm is gradually enhanced ( 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 λ of the fluorescent probe solution ex 485nm, the maximum emission wavelength λ em 605nm. Draw the graph with the fluorescence intensity value F as the ordinate, and get ClO - The working curve of concentration, the linear regression equation is F=26.382*[NaClO]+333.235, the unit of NaClO concentration is 10 -6 mol / L; the linear correlation coefficient is R 2 =0.9937, the best linear response range is 0μM–29.48μM...

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Abstract

The invention provides a fluorescent probe HM, and a preparation method and application thereof. The fluorescent probe is 7-(diethylamino)-3-[3-(2-hydroxy-5-methoxyphenyl)-3-oxo-1-propenyl]coumarin. The preparation method comprises the following steps: dissolving 7-(diethylamino)coumarin-3-formaldehyde and 1-(2-hydroxy-5-methoxyphenyl)ethanone in acetonitrile according to an equal molar ratio, dropwise adding piperidine, carrying out heating reflux for 20 hours, cooling to room temperature, carrying out reduced pressure suction filtration, collecting filter residues, and carrying out vacuum drying to obtain a product which is a red solid. The fluorescent probe is enhanced in detection of ClO<->, shows high sensitivity and good selectivity and stability, and has the advantages of simple and rapid detection process, accurate detection result and the like. In addition, by combining a laser confocal scanning microtechnique and a biological living body imaging technique, the novel fluorescent probe is successfully applied to detection of ClO<-> in cells and liver cancer mouse models.

Description

technical field [0001] The invention relates to a fluorescent probe, specifically to a fluorescent probe and a preparation method thereof, and the application of the probe to ClO in biological samples - detection. Background technique [0002] Reactive oxygen species (ROS) are highly reactive metabolites of oxygen, such as hydrogen peroxide (H 2 o 2 ), hypochlorous acid / hypochlorite (HOCl / OCl - ), singlet oxygen ( 1 o 2 ), peroxynitrite (ONOO - ), hydroxyl radicals (OH ) and ozone (O 3 ). Normal levels of ROS can maintain redox homeostasis in cells and tissues, and the oxidative stress caused by excessive ROS is an important factor involved in the occurrence and development of various human diseases and human aging. As catalyzed by myeloperoxidase (MPO), H 2 o 2 and chloride ions (Cl - ) The oxidation product produced by the reaction, OCl - It is a strong oxidizing ROS. OCl - Can interact with DNA, proteins and lipids and is involved in a variety of biological ...

Claims

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Application Information

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IPC IPC(8): C07D311/16C09K11/06G01N21/64
CPCC07D311/16C09K11/06G01N21/64C09K2211/1088
Inventor 张永斌段月香王娟娟钞建宾
Owner SHANXI UNIV
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