Lysosome-targeted photo-controlled fluorescent molecular switch, and synthesis method and application thereof

A technology of fluorescent molecules and synthesis methods, applied in the field of light-controlled fluorescent molecular switches and their synthesis, can solve the problems of photoactivation performance failure, limited application, fluorescence interference, etc., and achieve good imaging effects

Active Publication Date: 2019-09-24
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, when the rhodamine spiramide dye is exposed to the acidic environment in the lysosome, the fluorescence generated by its acid activation will seriously interfere or even lead to the complete failure of the photoactivation performance. Applications in volumetric super-resolution imaging

Method used

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  • Lysosome-targeted photo-controlled fluorescent molecular switch, and synthesis method and application thereof
  • Lysosome-targeted photo-controlled fluorescent molecular switch, and synthesis method and application thereof
  • Lysosome-targeted photo-controlled fluorescent molecular switch, and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] 3-amino-substituted rhodamine ethyl morpholine spiroamide (P1) synthetic route and product structure are as follows:

[0025]

[0026] 3-Nitrorhodamine (2 mmol, 0.974 g) and 2-ethylaminomorpholine (2 mmol, 0.146 g) were dissolved in absolute ethanol (35 mL). The temperature was raised to 78°C for reflux, and after stirring for 4 hours, the solvent was evaporated under reduced pressure, and the product was separated and purified by column chromatography (silica gel, petroleum ether / ethyl acetate, 4:1v / v) to obtain a light yellow powder (1.14g, 95 %). Then all the powder was dissolved in methanol (5mL), stirred under hydrogen atmosphere and palladium carbon (10%wt) catalysis for 1 hour, the filtrate was taken by suction filtration, and the final white powder product P1 (1.07g , 99%).

[0027] The powder product was characterized by NMR, mass spectrometry and high resolution mass spectrometry. figure 1 , figure 2 , image 3 shown.

[0028] 1 H NMR (400MHz, CDCl...

Embodiment 2

[0031] The product P1 in Example 1 was dissolved in methylene chloride / methanol (9 / 1, v / v) mixed solvent (concentration is 10 - 5 M), trifluoroacetic acid (2.3 μL, 1000 eq) was added to the mixed solution. Time-resolved UV-Vis absorption spectra were measured before and after acid addition ( Figure 4 ). The results showed that the absorbance at the maximum absorption wavelength of P1 did not increase with the increase of acidification time, indicating that the P1 molecule had the property of acid resistance.

Embodiment 3

[0033] MCF-7 cells were co-stained with the product 3-amino-substituted rhodamine ethylmorpholine spiroamide P1 (10 μM) in Example 1 and a commercial lysosomal labeling dye (LTG, 0.1 μM), and the MCF-7 cells were cultured by laser confocal An inverted microscope was used to observe the fluorescent staining in the two channels in real time. The excitation light wavelength of the green channel was 488nm, and the fluorescence signal in the 500-550nm band was collected. The excitation light wavelength of the red channel was 561nm, and the fluorescence signal in the 580-653nm band was collected. Comparative observation found that the fluorescent signal in the lysosome can be observed in the green channel after 0.5 hours of staining, while the red channel still has no obvious fluorescent signal in the lysosome after 2 hours of staining, and then irradiated in situ with 375nm ultraviolet light. The cells were irradiated, and the fluorescence images of the two channels were collected f...

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Abstract

The invention provides a lysosome-targeted photo-controlled fluorescent molecular switch, and a synthesis method and an application thereof. The specific molecular structure of the molecular switch is 3-amino-substituted rhodamine ethylmorpholinylamide, and the structural formula of the molecular switch is represented by formula (1). The lysosome-targeted photo-controlled fluorescent molecular switch of the invention has acid resistance, and also retains the photoactivation performance, so like acid-resistant photoactivated dyes can be used in a super-resolution imaging technique in lysosomes without being interfered by the pH value of a biological environment in order to achieve a good imaging effect. In addition, the lysosome-targeted photo-controlled fluorescent molecular switch of the invention can also be used in the fields of sensing and detection as a molecular fluorescent probe.

Description

technical field [0001] The invention belongs to the field of molecular switches, and in particular relates to a lysosome-targeted light-controlled fluorescent molecular switch and its synthesis method and application. Background technique [0002] As an important acidic organelle in eukaryotic cells, lysosomes contain more than 60 kinds of acid hydrolases, cathepsins, and various specific membrane proteins. It not only has the function of intracellular digestion, but also has the function of regulating secretion in some cases. When the number and distribution of lysosomes are abnormal due to their own variation or external influence, it may cause lung diseases (silicosis, tuberculosis, etc.) ), lysosomal storage diseases (Taiwan-Sarritz syndrome, type II glycogen storage disease, cellular inclusion disease, etc.), tumors and other diseases. As the "digestive organ" in the cell, the research on lysosome has always been a hot spot in life science. [0003] Fluorescence imagi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C09B57/00C09B11/24C09K11/06G01N21/64
CPCC07D491/107C09B11/24C09B57/00C09K11/06C09K2211/1029C09K2211/1033C09K2211/1088G01N21/6402G01N21/6428
Inventor 徐兆超祁清凯陈婕
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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