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A fluorescent probe for targeting and labeling eye lens epithelial cells, its preparation and application

A technology of fluorescent probes and epithelial cells, which is applied in the field of fluorescent sensing materials, can solve the problem that eye lens epithelial cells cannot be completely removed at one time, and achieve the effect of avoiding postoperative complications and inhibiting proliferation

Inactive Publication Date: 2019-02-19
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In view of the problem that eye lens epithelial cells cannot be completely removed at one time during the current cataract operation and cause postoperative complications, one of the purposes of the present invention is to provide a fluorescent probe for targeting and labeling eye lens epithelial cells. At the same time, it has the functions of in situ target labeling of eye lens epithelial cells and inhibition of eye lens epithelial cell proliferation, and has a good application prospect in the field of cataract treatment; the second purpose is to provide a fluorescent probe for target labeling of eye lens epithelial cells The preparation method, described preparation method is simple, easy to operate

Method used

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  • A fluorescent probe for targeting and labeling eye lens epithelial cells, its preparation and application
  • A fluorescent probe for targeting and labeling eye lens epithelial cells, its preparation and application
  • A fluorescent probe for targeting and labeling eye lens epithelial cells, its preparation and application

Examples

Experimental program
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Effect test

Embodiment 1

[0040] (1) Take 56.8mg (0.1mmol) of 1,4-bis(4-bromophenyl)-2,5-diphenyl-1,4-dihydropyrrolo[3,2-b]pyrrole, 45mg (0.3mmol) 4-formyl phenylboronic acid, 6mg (0.005mmol) tetrakis (triphenylphosphine) palladium, 67.5mg (0.5mmol) potassium carbonate were added to a 100mL two-necked round-bottomed flask, vacuumed and filled with nitrogen three times, and 12mL was added to remove A mixed solvent of toluene and methanol (volume ratio of toluene and methanol is 3:1), after reflux at 110°C for 8h, cool the reaction solution in the two-necked round-bottomed flask to room temperature, and then add a volume twice the volume of the reaction solution A mixture of water and dichloromethane (V 水 :V 二氯甲烷 =1:1) to extract the reaction solution, dry the separated organic phase with anhydrous magnesium sulfate, and then use a rotary evaporator to spin dry at 40°C to obtain a crude product; the crude product is separated and purified by column chromatography, and placed Dry it in a vacuum drying o...

Embodiment 2

[0051] (1) Take 113.6mg (0.2mmol) of 1,4-bis(4-bromophenyl)-2,5-diphenyl-1,4-dihydropyrrolo[3,2-b]pyrrole, 90mg (0.6mmol) 4-formyl phenylboronic acid, 12mg (0.01mmol) tetrakis (triphenylphosphine) palladium, 135mg (1mmol) potassium carbonate were added to a 100mL two-necked round-bottomed flask, evacuated and filled with nitrogen three times, and added 12mL of deoxygenated A mixed solvent of toluene and methanol (the volume ratio of toluene and methanol is 3:1), after reflux at 110°C for 8 hours, cool the reaction solution in the two-necked round bottom flask to room temperature, and then add water twice the volume of the reaction solution and dichloromethane mixture (V 水 :V 二氯甲烷 =1:1) to extract the reaction solution, dry the separated organic phase with anhydrous magnesium sulfate, and then use a rotary evaporator to spin dry at 40°C to obtain a crude product; the crude product is separated and purified by column chromatography, and placed Dry it in a vacuum oven at 25°C t...

Embodiment 3

[0064] (1) 0.95mg DPPHP-2CHO prepared in Example 1 was dissolved in 1.5mL DMSO to make a concentration of 1×10 -3 mol / L solution g, then take 0.1mL solution g and dilute it with DMEM to a concentration of 1×10-4 mol / L solution h, filter solution h with a microporous membrane with a pore size of 0.22 μm to obtain solution I;

[0065] (2) Passage the rabbit eye lens epithelial cells (BLE cells) and ICR mouse embryonic fibroblasts (MEF cells) that have covered the bottom of the culture dish to a small culture dish (Φ=20mm) with slides at the bottom. ), each group contains three parallel experiments, at 37℃, CO 2 Cultivate for 12 hours in an incubator with a volume fraction of 5%;

[0066] (3) Aspirate the medium from the culture dish containing the cells, add solution I with a volume of 0.5mL and place it under a laser confocal microscope (excitation wavelength 543nm, wavelength range 555-700nm) to observe the concentration of solution I in the BLE cell and MEF cell. Imaging si...

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Abstract

The invention relates to a fluorescent probe for targeted marking eye lens epithelial cells and a preparation method and application thereof and belongs to the field of fluorescent sensing materials. The fluorescent probe is DPPHP-2CHO, has functions of in-situ targeted marking of the eye lens epithelial cells and inhibiting of lens epithelial cell proliferation and is suitable for the field of treating cataract. The preparation method includes: adding 1, 4-bis(4-bromophenyl)-2, 5-diphenyl-1, 4-dihydropyroole[3, 2-b] pyrrole, 4-formylbenzeneboronic acid and a catalyst into a reaction container; vacuumizing, feeding shielding gas for more than twice, adding a deoxidized solvent I, and allowing backflow reaction; cooling, adding a solvent II for extraction, using anhydrous magnesium sulfate to dry an organic phase obtained by extraction and separation, and spin-drying the organic phase to obtain a crude product; subjecting the crude product to column chromatography separation and purification, and drying to obtain solid powder which is the fluorescent probe.

Description

technical field [0001] The invention relates to a fluorescent probe for targeting and marking eye lens epithelial cells, its preparation and application, in particular to a fluorescent probe for 2,5-diphenylpyrrole derivatives containing 4,4'-dialdehyde groups. The needle, its preparation and application belong to the field of fluorescent sensing materials. Background technique [0002] At present, cataract has become the main cause of blindness in the world. In my country, the number of blindness due to this disease accounts for about 10% of the global cataract blindness, and there are 1 million new cataract cases every year, especially with the aging of the population. Still growing. Although cataract extraction and intraocular lens implantation are the most mature and ideal methods for treating cataracts, the intraocular lens still has certain defects and cannot completely replace the function of the human eye lens, especially for adolescents and children. There are some...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04C09K11/06A61K49/00
CPCA61K49/0021A61K49/006C07D487/04C09K11/06C09K2211/1007C09K2211/1029
Inventor 董宇平陈笛笛彭喆朱思泉佟斌赵阳
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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