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

A technology of fluorescent molecule and synthesis method, which is applied in the field of acid-resistant light-controlled fluorescent molecular switch and its synthesis, can solve the problems of switching interference, performance failure of light-controlled molecular switch, inability of fluorescent probe to be applied to super-resolution fluorescence imaging, etc.

Active Publication Date: 2021-06-04
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
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  • Application Information

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Problems solved by technology

[0004] Rhodamine spiroamide realizes the "on-off" control of fluorescent molecules with visible light, which is extremely important and meaningful for biological imaging, but there is still a serious disadvantage of this type of molecule that limits its 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
Comparison scheme
Effect test

Embodiment 1

[0033] 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 When, its molecular (P1) synthetic route and product structure are as follows:

[0034]

[0035] 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 autoclaving.

[0036] The product was characteri...

Embodiment 2

[0040] 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:

[0041]

[0042] 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%).

[0043] The 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 NMR (101MH...

Embodiment 3

[0047] 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:

[0048]

[0049] 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%).

[0050] The 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 CNMR (101MHz, CDCl 3 )δ169.30,168.85,158.27,15...

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Abstract

The invention provides an acid-resistant light-controlled fluorescent molecular switch and its synthesis method and application. The specific molecular structure of the molecular switch uses rhodamine spiramide substituted with 3-primary amine or secondary amine as the basic structural unit, and its structural formula is as (1 ) shown. The acid-resistant light-controlled fluorescent molecular switch of the invention is applied in super-resolution fluorescent imaging, molecular probes, fluorescent sensing and other fields. The 3-primary amine or secondary amine substituted rhodamine spiroamide of the present invention not only has the performance of acid resistance, but also retains the performance of light-controlled molecular switch. Therefore, this kind of acid-resistant light-controlled fluorescent molecular switch can be applied in super-resolution imaging technology based on single-molecule localization, and it is not disturbed by the pH in the biological environment. In addition, the acid-resistant light-controlled fluorescent molecular switch of 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): C07D491/107C09B11/12C09K11/06G01N21/64
CPCC09B11/12C09K11/06C09K2211/1007C09K2211/1029C09K2211/1033C09K2211/1088G01N21/6486
Inventor 徐兆超祁清凯
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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