Visible light photo-controlled acid-resistant fluorescent molecular switch and synthesis method thereof

A technology of fluorescent molecules and synthesis methods, applied in the field of acid-resistant fluorescent molecular switches and their synthesis, can solve the problems of failure of light-controlled fluorescent molecular switches, weak absorption, interference of fluorescent signals, etc.

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

AI Technical Summary

Problems solved by technology

There are many acidic environments in cells (such as lysosomes, protein acidic sites, etc.), when rhodamine spiramide dyes are applied in these acidic environments, the fluorescent signal generated by the acid-controlled molecular switch will seriously interfere or even lead to photocontrol. The performance of fluorescent molecular switches is completely ineffective, so fluorescent probes based on such dyes in acidic environments cannot currently be applied to super-resolution fluorescence imaging
In addition, most of the reported rhodamine spiroamides can only use ultraviolet light (<375nm) to control the fluorescent molecular switch, and ultraviolet light is phototoxic to organisms and is not conducive to live cell imaging.
Although S.W.Hell et al. used a long-wavelength two-photon laser to activate the fluorescence of rhodamine spiramide and applied it to super-resolution imaging, the power of the two-photon laser is several orders of magnitude larger than that of the single-photon laser, which will also affect the imaged organisms. irreparable photodamage
The maximum absorption wavelength of the visible light-controlled molecular switch dye developed by W.E.Moerner et al. is about 380nm, but the absorption is very weak at the 405nm laser excitation wavelength acceptable for cell imaging, so it is difficult to efficiently use the 405nm laser to realize the light-controlled fluorescent molecular switch

Method used

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  • Visible light photo-controlled acid-resistant fluorescent molecular switch and synthesis method thereof
  • Visible light photo-controlled acid-resistant fluorescent molecular switch and synthesis method thereof
  • Visible light photo-controlled acid-resistant fluorescent molecular switch and synthesis method thereof

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Experimental program
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Effect test

Embodiment 1

[0038] When R 1 = R 2 = R 3 = R 4 =C 2 h 5 ,R 5 =H, X=O, Y=H, when Z=O, its molecular (P1) synthesis route and product structure are as follows:

[0039]

[0040] Synthesis steps and characterization: 3-Nitrorhodamine (2.92g, 6mmol) and phosphorus oxychloride (5.6mL, 60mmol) were placed in 1,2-dichloroethane (150mL), heated to 84°C under reflux, stirred After 2 hours the solvent was evaporated to give a dark purple oily liquid. The crude acid chloride product was dissolved in dichloromethane (100mL), then added dropwise to a mixed solution of triethylamine (3mL) and 6-(4-aminophenylethynyl)naphthalene anhydride (1.88g, 6mmol), and stirred at room temperature for 24 hours Afterwards, the solvent was evaporated under reduced pressure, and the residue was separated by column chromatography (silica gel, dichloromethane / ethyl acetate, 30:1 v / v) to obtain a yellow powdery intermediate (2.44 g, 52%). Take the above yellow powder (1.56g, 2mmol), stannous chloride dihydrate ...

Embodiment 2

[0048] When R 1 = R 2 = R 3 = R 4 =C 2 h 5 ,R 5 =CH 3 CO, X=O, Y=H, when Z=O, its molecular (P2) synthesis route and product structure are as follows:

[0049]

[0050] Synthesis steps and characterization: P1 (0.75g, 1mmol) and acetyl chloride (0.12g, 1.5mmol) were mixed in dichloromethane (10mL), stirred for 2 hours, and the solvent was evaporated under reduced pressure, and the crude product was passed through column chromatography (silica gel, Ethyl acetate / petroleum ether, 1:3 v / v) isolated the product P2 as a yellow powder (0.76 g, 96%).

[0051] The product was characterized by NMR and mass spectrometry:

[0052] 1 H NMR (400MHz, CDCl 3 )δ10.58(s,1H),8.75(d,J=8.2Hz,1H),8.65(d,J=7.2Hz,1H),8.55(d,J=7.7Hz,1H),8.51(d, J=8.2Hz,1H),7.92(d,J=7.7Hz,1H),7.90–7.82(m,1H),7.56–7.43(m,3H),7.00(d,J=8.5Hz,2H), 6.81(d, J=7.6Hz, 1H), 6.67(d, J=8.8Hz, 2H), 6.37–6.26(m, 4H), 3.33(q, J=7.0Hz, 8H), 2.31(s, 3H ), 1.17 (t, J=7.0Hz, 12H). 13 CNMR (101MHz, CDCl 3)δ169.31,168.9...

Embodiment 3

[0058] When R 1 = R 2 = R 3 = R 4 =C 2 h 5 , R 5 =H, X=O, Y=H, Z=C 6 h 12 N 2 During 0, its molecular (P3) synthesis route and product structure are as follows:

[0059]

[0060] Synthesis steps and characterization: P1 (0.37g, 0.5mmol) and 2-ethylaminomorpholine (0.19g, 1.5mmol) were mixed in absolute ethanol (10mL), heated to 78°C and refluxed, stirred for 10 hours and then decompressed The solvent was evaporated, and the residue was separated by column chromatography (silica gel, ethyl acetate / petroleum ether, 1:2 v / v) to obtain a yellow powder product P3 (0.36 g, 84%).

[0061] The product was characterized by NMR and mass spectrometry:

[0062] 1 H NMR (400MHz, CDCl 3 )δ8.66(d, J=8.3Hz, 1H), 8.61(d, J=7.1Hz, 1H), 8.52(d, J=7.7Hz, 1H), 7.87(d, J=7.6Hz, 1H) ,7.79(t,J=7.8Hz,1H),7.44(d,J=8.4Hz,2H),7.22(t,J=7.7Hz,1H),7.10(d,J=8.5Hz,2H),6.76 (d, J=8.6Hz, 2H), 6.60(d, J=8.0Hz, 1H), 6.37(d, J=7.4Hz, 1H), 6.32(d, J=10.4Hz, 4H), 5.44(s ,2H),4.34(t,J=6.8Hz,2H),3.68...

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Abstract

The invention provides a visible light photo-controlled acid-resistant fluorescent molecular switch and a synthesis method thereof. The specific molecular structure of the molecular switch is 3-primary amine or secondary amine substituted rhodamine spiroamide as a basic structural unit, and the structural formula of the molecular switch is represented by formula (1). The 3-primary amine or secondary amine substituted rhodamine spiroamide of the invention has acid resistance, and also retains the photoactivation performance, so like photoactivated acid-resistant fluorescent molecular switch dyes can be used in a living cell super-resolution imaging technique, and are not interfered by the acidic environment. The 3-primary amine or secondary amine substituted rhodamine spiroamide dye also can be used in 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 an acid-resistant fluorescent molecular switch controlled by visible light and a synthesis method thereof. 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...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C07D519/00C09B11/24C09B57/08C09K11/06G01N21/64
CPCC07D491/107C07D519/00C09B11/24C09B57/08C09K11/06C09K2211/1029C09K2211/1044C09K2211/1088G01N21/6402G01N21/6428G01N21/6486
Inventor 徐兆超祁清凯
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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