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A kind of acid-resistant light-controlled fluorescent molecular switch and its synthesis method and application

A technology of fluorescent molecules and synthesis methods, applied in the field of acid-resistant photo-controlled fluorescent molecular switches and their synthesis, can solve problems such as the failure of the performance of photo-controlled molecular switches, the inability of fluorescent probes to apply super-resolution fluorescence imaging, and switching interference.

Active Publication Date: 2021-11-09
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Rhodamine spiroamide has realized the "on-off" control of fluorescent molecules with visible light, which is extremely important and meaningful for biological imaging, but this type of molecule still has a serious disadvantage that limits its general application in super-resolution imaging. That is, the molecular switch of rhodamine spiramide can not only be controlled by light, but also can be controlled by acid and base, that is, under acidic conditions, the rhodamine amide spiro ring opens to become a luminescent open ring structure
However, there are many acidic environments in cells (such as lysosomes, acidic sites of proteins, etc.), when rhodamine spiramide dyes are applied in these acidic environments, the acid-controlled switches will seriously interfere or even lead to photo-controlled molecular switches. The performance is completely lost, so fluorescent probes based on this type of dye cannot currently be applied to super-resolution fluorescence imaging in acidic environments

Method used

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  • A kind of acid-resistant light-controlled fluorescent molecular switch and its synthesis method and application
  • A kind of acid-resistant light-controlled fluorescent molecular switch and its synthesis method and application
  • A kind of acid-resistant light-controlled fluorescent molecular switch and its synthesis method and application

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Experimental program
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Effect test

Embodiment 1

[0060] When R 1 =R 2 =R 3 =R 4 =C 2 h 5 , R 5 =H, X=O, Y=H, Z=C 4 h 9 , the synthesis route and product structure of the acid-resistant light-controlled fluorescent molecular switch P1 are as follows:

[0061]

[0062] Synthesis steps and characterization: 3-Nitrorhodamine (5mmol, 2.4g) and n-butylamine (20mmol, 1.4g) were dissolved in absolute ethanol (50mL). The temperature was raised to 78°C for reflux, and after stirring for 8 hours, the solvent was evaporated under reduced pressure, and the product was separated and purified by silica gel chromatography (petroleum ether / ethyl acetate, 8:1v / v), and the obtained light yellow powder (2.6g, 95% ). Then all the powder was dissolved in methanol / dichloromethane (50mL, 3:1v / v) mixed solvent, under hydrogen atmosphere, by palladium carbon (0.21g, 10%wt) catalytic reduction, the filtrate was taken by suction filtration, and the The final product (2 g, 98%) was obtained as a white powder after removal of the solvent by ...

Embodiment 2

[0067] When R 1 =R 2 =R 3 =R 4 =C 2 h 5 , R 5 =CH 3 , X=O, Y=H, Z=C 4 h 9 When, its molecular (P2) synthesis route and product structure are as follows:

[0068]

[0069] Synthesis steps and characterization: P1 (0.25g, 0.5mmol), iodomethane (0.28g, 2mmol) and potassium carbonate (0.34g, 2.5mmol) were mixed in acetonitrile (8mL), stirred at reflux for 10 hours, cooled to room temperature and filtered The filtrate was obtained, and the solvent was evaporated under reduced pressure. The crude product was separated and purified by column chromatography (silica gel, petroleum ether / ethyl acetate, 10:1 v / v) to obtain white powder P2 (0.17 g, 65%).

[0070] The white powder product was characterized by NMR and mass spectrometry: 1 H NMR (400MHz, CDCl 3 )δ7.23(t, J=7.9Hz, 1H), 6.75(d, J=4.9Hz, 1H), 6.57(t, J=9.3Hz, 2H), 6.49(d, J=8.1Hz, 1H) ,6.41–6.22(m,5H),3.33(q,J=7.0Hz,8H),3.04(s,2H),2.97(d,J=4.9Hz,3H),1.16(t,J=6.9Hz, 12H), 1.07(s, 4H), 0.67(t, J=6.5Hz, 3H). 13 C ...

Embodiment 3

[0074] When R 1 =R 2 =R 3 =R 4 =C 2 h 5 , R 5 =CH 3 CO, X=O, Y=H, Z=C 4 h 9 When, its molecular (P3) synthesis route and product structure are as follows:

[0075]

[0076] Synthesis steps and characterization: P1 (0.25g, 0.5mmol) and acetyl chloride (58mg, 0.75mmol) were mixed in dichloromethane (5mL), stirred for 2 hours, and the solvent was evaporated under reduced pressure, and the crude product was passed through column chromatography (silica gel, Petroleum ether / ethyl acetate, 8:1 v / v) was separated and purified to obtain white powder P3 (0.26 g, 95%).

[0077] The white powder product was characterized by NMR and mass spectrometry: 1 H NMR (400MHz, CDCl 3 )δ10.60(s,1H),8.43(d,J=8.2Hz,1H),7.39(t,J=7.9Hz,1H),6.74(d,J=7.6Hz,1H),6.46(d, J=8.8Hz, 2H), 6.38(d, J=2.6Hz, 2H), 6.28(dd, J=8.9, 2.6Hz, 2H), 3.34(q, J=7.0Hz, 8H), 3.06(t, J=7.0Hz, 2H), 2.29(s, 3H), 1.17(t, J=7.0Hz, 12H), 1.12–1.02(m, 4H), 0.69(t, J=6.7Hz, 3H). 13 C NMR (101MHz, CDCl 3 )δ169.30,168.8...

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Abstract

The invention provides an acid-resistant light-controlled fluorescent molecular switch and its synthesis method and application. The chemical structure characteristics of the light-controlled fluorescent molecular switch are as follows: the parent body of the fluorophore is a rhodamine dye, and the parent body of the rhodamine chromophore has different substituents R 1 , R 2 , R 3 , R 4 , X, Y, there are primary or secondary amine substituents in the ortho position of the lactam, and the specific structure is shown in formula (1). The acid-resistant light-controlled fluorescent molecular switch is used as a fluorescent probe in super-resolution fluorescence imaging, sensing and detection. The 3-primary amine or secondary amine substituted rhodamine spiramide developed by the acid-resistant light-controlled fluorescent molecular switch of the present invention not only has acid-resistant performance, but also retains the performance of the light-controlled molecular switch. Therefore, this type of acid-resistant light-controlled fluorescent molecular switch can be used in In the super-resolution imaging technology based on single-molecule localization, it is not disturbed by the pH in the biological environment. In addition, the acid-resistant light-controlled fluorescent molecular switch in the present invention can also be used as a molecular fluorescent probe in the field of sensing and detection.

Description

technical field [0001] The invention belongs to the field of molecular switches, in particular to an acid-resistant light-controlled fluorescent molecular switch and its synthesis method and application. Background technique [0002] In recent years, a series of ultra-high-resolution fluorescence imaging techniques have been developed, among which photoactivated localization microscopy (PLAM) and stochastic optical reconstruction microscopy (STORM or dSTORM) based on single-molecule localization have enabled the spatial resolution of optical microscopy to reach Unprecedented height (20nm). At present, super-resolution microscopy imaging technology has been widely used in life science research. However, although super-resolution microscopy imaging technology has made great progress, advancing the spatial resolution of fluorescence microscopy to 20 nanometers, super-resolution fluorescence microscopy imaging The technology still faces many technical problems, one of which is ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/107C07D519/00C09K11/06G01N21/64
CPCC07D491/107C07D519/00C09K11/06C09K2211/1007C09K2211/1029C09K2211/1033C09K2211/1044C09K2211/1088G01N21/6402G01N21/6428G01N21/6458G01N2021/6439
Inventor 徐兆超祁清凯
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI