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Preparation and application of rhodamine hypochlorous acid fluorescent probe capable of targeting lysosome

A technology of fluorescent probes and lysosomes, which is applied in the field of synthesis of new HOCl fluorescent probes, can solve the problem of insufficient hypochlorous acid fluorescent probes

Pending Publication Date: 2018-09-11
山东省第一医科大学
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, there are not many reports on lysosome-targeted hypochlorous acid fluorescent probes today.
[0005] In addition, the reported probe needs to be in a mixture of a higher content of organic solvent and buffer solution to achieve the detection of hypochlorous acid [Qiao L. et al, J. Mater. Chem. B 5 (2017) 525 -530; Li K. et al, Chem. Commun. 53 (2017) 5539-5541; Tang Z. et al, RSC Adv. 5 (2015)99664-99668; Shen S.L. et al, Sens. Actuators B 263 (2018 ) 252-257], however, these probes are not suitable for the detection of HOCl in the intracellular environment

Method used

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  • Preparation and application of rhodamine hypochlorous acid fluorescent probe capable of targeting lysosome
  • Preparation and application of rhodamine hypochlorous acid fluorescent probe capable of targeting lysosome
  • Preparation and application of rhodamine hypochlorous acid fluorescent probe capable of targeting lysosome

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1: The synthetic route of probe sees figure 1 .

[0023] Compound 1 (2 mmol) was dissolved in 7 mL SOCl 2 , stirred at room temperature for 6 hours, and then removed the solvent under reduced pressure to obtain a yellow solid 2 (directly used in the next reaction without purification).

[0024] Dissolve compound 2 (2 mmol) in 50 mL of dry dichloromethane, add triethylamine (6 mmol) and compound 3 (1 mmol) respectively, stir at room temperature for about 6 h, then wash the reaction solution with water, anhydrous sodium sulfate After drying, the solvent was removed under reduced pressure, followed by separation and purification by column chromatography to obtain the probe LR1 of the present invention.

[0025] by 1 H NMR, 13 C NMR and HRMS characterize it, the data are as follows:

[0026] 1 H NMR (400 MHz, d 6 -DMSO), δ (ppm): 1.09 (t, 6H, J = 6.8 Hz, CH 3 ), 2.36(s, 4H, CH 2 ), 3.24 (br, 4H, CH 2 ), 3.32 (br, 4H, CH 2 ), 3.50 (br, 4H, CH 2 ), 3...

Embodiment 2

[0029] Example 2: Selectivity of the probes of the present invention to hypochlorous acid.

[0030] Prepare 1 μM probe in PBS buffer solution (containing 0.5% ethanol, pH 5.00). Then add common metal ions, anions and active oxides respectively. Result shows that probe of the present invention has good selectivity to hypochlorous acid, as figure 2 shown. (1): blank, (2): H 2 o 2 , (3): t -BuOOH, (4): t -BuO•, (5): 1 o 2 , (6): - o 2 , (7): ON, (8): •OH, (9): ONOO - , (10): Br - , (11): Cl - , (12): I - , (13): CO 3 2- , (14):SO 4 2- , (15): NO 3 - , (16): Na + , (17): K + , (18): Ca 2+ , (19): Mg 2+ , (20): Zn 2+ , (21):Cu 2+ , (22): Hg 2+ , (23): HOCl. Conditions: [HOCl] = 3 µM, [Other ROS / RNS] = 10 µM, [Anions] = 50 µM, [Cations] = 5 µM.

Embodiment 3

[0031] Embodiment 3: Detection of the change of the concentration of hypochlorous acid in the solution by the probe of the present invention.

[0032]Prepare 1 μM probe in PBS buffer solution (containing 0.5% ethanol, pH 5.00). Add 0 μM, 0.125 μM, 0.25 μM, 0.375 μM, 0.5 μM, 0.625 μM, 0.75 μM, 0.875 μM, 1.0 μM, 1.25 μM, 1.5 μM, 1.75 μM, 2.0 μM, 2.25 μM, 2.5 μM, 2.75 eq, 3.0 eq hypochlorous acid solution, and then carry out fluorescence spectrum analysis, the results show that the fluorescence intensity becomes stronger with the increase of hypochlorous acid concentration, such as image 3 shown.

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Abstract

The invention discloses a rhodamine hypochlorous acid fluorescent probe capable of targeting a lysosome. According to the probe, a morpholine structure is used as a locating group of the lysosome, when hypochlorous acid exists, a rhodamine group is converted into an open-loop structure, strong fluorescent light is emitted from a portion at 582 nm, and the intensity of the fluorescent light is improved along with the increase of the concentration of hypochlorous acid. The probe has high selectivity and sensitivity to hypochlorous acid and high response speed, and can target the lysosome.

Description

technical field [0001] The invention relates to the synthesis and application of a novel HOCl fluorescent probe, which can be used to detect the change of HOCl concentration in cell lysosomes. Background technique [0002] Hypochlorous acid is a weak acid, which is an important active oxide in living organisms and plays an important role in the redox balance in cells. When hypochlorous acid is too much, it will lead to many diseases in the body, such as: Alzheimer's disease, rheumatoid arthritis, cancer and so on. The real-time monitoring of hypochlorous acid concentration plays an important role, so the detection of hypochlorous acid in organisms has become a hot topic for scholars today. [0003] Fluorescent probes have now become an important tool for detecting active small molecules in cells. It has good selectivity, high sensitivity, and a small amount of sample with little toxicity to cells. Therefore, fluorescent probes have gradually become a research hotspot for s...

Claims

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Application Information

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IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06C09K2211/1007C09K2211/1029C09K2211/1033C09K2211/1044C09K2211/1088G01N21/6428G01N2021/6439
Inventor 申世立曹晓群黄晓晴
Owner 山东省第一医科大学