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Rhodamine B type fluorescent probe capable of being applied to detection of HOCl in cytolysosome

A technology of fluorescent probes and lysosomes, applied in the direction of fluorescence/phosphorescence, luminescent materials, measuring devices, etc., can solve the problems that hypochlorous acid fluorescent probes do not have organelle targeting function, are not applicable, and are difficult to study

Inactive Publication Date: 2018-11-09
SHANDONG FIRST MEDICAL UNIV & SHANDONG ACADEMY OF MEDICAL SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the reported fluorescent probes for hypochlorous acid do not have the function of targeting organelles, which brings difficulties to the study of HOCl at the organelle level.
[0005] In addition, the reported HOCl probes need to be in more organic solvent systems to achieve the detection of HOCl
However, the intracellular organic solvent content is extremely low, therefore, these probes are not suitable for the test of intracellular HOCl [Shen S.L. et al, Sens. Actuators B 254 (2018) 736-741, Zhang Y.R. et al, Sens. Actuators B240 ( 2017) 18-36]

Method used

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  • Rhodamine B type fluorescent probe capable of being applied to detection of HOCl in cytolysosome
  • Rhodamine B type fluorescent probe capable of being applied to detection of HOCl in cytolysosome
  • Rhodamine B type fluorescent probe capable of being applied to detection of HOCl in cytolysosome

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Experimental program
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Effect test

Embodiment 1

[0023] Embodiment 1: The synthetic route of probe sees figure 1 .

[0024] Compound 1 (2 mmol) was dissolved in 10 mL SOCl 2 After heating to reflux for 2 hours, the solvent was removed under reduced pressure to obtain solid 2 (not purified, directly used in the next reaction).

[0025] Compound 2 (2 mmol) was dissolved in 10 mL of dry pyridine, stirred at room temperature for about 1 hour, then compound 3 (1 mmol) was added to the reaction system, and stirred at room temperature for 12 hours. The reaction solution was poured into 150 mL of dichloromethane, then washed three times with 200 mL of water, the organic phase was dried with anhydrous sodium sulfate, the solvent was removed under reduced pressure, and then separated by column chromatography to obtain the probe RL1 of the present invention, White solid, 45% yield.

[0026] by 1 H NMR, 13 C NMR and HRMS carry out its structure, the data are as follows:

[0027] 1 H NMR (400 MHz, d 6 -DMSO), δ (ppm): 1.09 (t, 1...

Embodiment 2

[0031] Prepare 1 μM probe in PBS buffer solution (containing 1% ethanol, pH 5.00). Then add the following ions respectively, 1: blank, 2: Na + , 3: K + , 4: Ca 2+ , 5: Mg 2+ , 6: Zn 2+ , 7: Al 3+ , 8: Cu 2+ , 9: Mn 2+ , 10: Li + , 11:Co 2+ , 12: Hg 2+ , 13: Pb 2+ , 14: F - , 15: Cl - , 16: Br - , 17: I - , 18: AcO - , 19: NO 3 - ,20: NO 2 - , 21: S 2 o 3 2- , 22: HCO 3 - , 23: HPO 4 2- , 24: HS - , 25: SO 4 2- , 26: Asn, 27: Asp, 28: Glu, 29: Gly, 30: Hcy, 31: Ser, 32: Trp, 33: Cys, 34: H 2 o 2 , 35: t -BuOOH,36: t -BuO•, 37: 1 o 2 , 38: - o 2 , 39: •OH, 40: HOCl. Concentration: 40 µM for (2)-(39); 3 µM for (40). Find by fluorescence test, only when HOCl exists, probe just has fluorescent emission at 592 nm, and other ions can not cause probe to change fluorescence at 592 nm, so probe of the present invention is sensitive to hypochlorous acid have good selectivity, such as figure 2 shown.

Embodiment 3

[0033]Prepare 1 μM probe in PBS buffer solution (containing 1% ethanol, pH 5.00). Add 0 μM, 0.1 μM, 0.2 μM, 0.3 μM, 0.4 μM, 0.5 μM, 0.6 μM, 0.7 μM, 0.8 μM, 0.9 μM, 1.0 μM, 1.5 μM, 2.0 μM, 2.5 μM, 3.0 μM, 3.5 μM hypochlorous acid, and then carry out fluorescence spectrum analysis, the results show that the fluorescence emission of the probe at 592nm becomes stronger with the increase of hypochlorous acid concentration, as shown in image 3 As shown, figure (a) is the fluorescence emission diagram of the probe in different concentrations of HOCl, and figure (b) is the relationship between the fluorescence intensity of the probe at 592 nm and the concentration of HOCl. The experimental results show that the probe can be used for the detection of HOCl in solution.

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Abstract

The invention discloses a rhodamine B type fluorescent probe capable of being applied to detection of HOCl in cytolysosome. The probe takes rhodamine B as fluorophore and thiodihydrazide as a responsegroup; a morpholine structure is introduced into a probe structure and is used as a lysosome positioning group. When no HOCl exists, the probe does not emit fluorescent light; when the HOCl exists, the probe emits strong fluorescent light at a part with the wavelength of 592nm. The fluorescence intensity becomes strong along the increasing of the concentration of hypochlorous acid; the concentration of the HOCl is in a range of 0 to 2muM, and the fluorescence intensity and the concentration of the hypochlorous acid are linearly increased. The probe has the characteristics of high selectivity,high sensitivity and rapid response, can be applied to the detection of the HOCl in the cytolysosome and has a wide application prospect.

Description

technical field [0001] The invention relates to a rhodamine B fluorescent probe which can be applied to the detection of HOCl in the cell lysosome, and the probe can detect the change of the concentration of HOCl in the cell lysosome. Background technique [0002] HOCl is one of the important reactive oxygen species in organisms and plays an important role in the redox balance of cells. When pathogens invade organisms, cells will produce HOCl to oxidize and kill pathogens; but when the concentration of hypochlorous acid in cells is too high, it will cause abnormal cell function, which will lead to the occurrence of many diseases, such as Alzheimer's disease and rheumatoid arthritis , cancer, etc. Therefore, the realization of real-time monitoring of intracellular HOCl is of great significance for the study of diseases related to abnormal HOCl in organisms. [0003] Compared with traditional analysis methods, fluorescent probes have the advantages of high sensitivity, good ...

Claims

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Application Information

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IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06G01N21/6428
Inventor 申世立曹晓群黄晓晴
Owner SHANDONG FIRST MEDICAL UNIV & SHANDONG ACADEMY OF MEDICAL SCI
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