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Cell nucleus fluorescent probe with high brightness and high light stability

A fluorescent probe, high-brightness technology, applied in the field of fluorescence imaging, can solve the problems of time-consuming and labor-intensive, and achieve the effect of high photostability

Active Publication Date: 2020-06-26
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, most of these methods are time-consuming and labor-intensive, so it is imminent to develop new cell nuclear dyes with simple methods, high brightness and high photostability

Method used

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  • Cell nucleus fluorescent probe with high brightness and high light stability
  • Cell nucleus fluorescent probe with high brightness and high light stability
  • Cell nucleus fluorescent probe with high brightness and high light stability

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Synthesis of the nuclear probe OMor-Aze.

[0036] The intermediate Naph-Aze synthesis route and product structure are as follows:

[0037]

[0038] Weigh 4-bromo-1,8-naphthalene anhydride (3.0g, 10.9mmol), anhydrous copper sulfate (5.2g, 32.7mmol) in 10mL dry DMF, add azetidine (1.9mmol) under nitrogen protection g, 32.7 mmol), the temperature was raised to 140° C. to react for 20 h, and after cooling the reaction solution to room temperature, the reaction solution was slowly poured into ice water, and a large amount of orange solids were precipitated. The filtrate was removed by suction filtration, and the filter residue was dissolved in dichloromethane and purified by silica gel column chromatography (petroleum ether / dichloromethane=1 / 10, V / V) to obtain 1.1 g of orange solid powder Naph-Aze with a yield of 40%.

[0039] Its high-resolution mass spectrometry data are as follows:

[0040] HRMS (ESI): m / z: [M+H] + : Calculated: 254.0817, Experimented: 254.0883.

...

Embodiment 2

[0058] The synthesis route and product structure of nuclear probe Pid-Aze are as follows:

[0059]

[0060] Weigh Naph-Aze (0.1g, 0.4mmol) in 5mL of absolute ethanol, add 1-aminopiperidine (1.2g, 12mmol), heat the reaction solution to 80°C for 8h, then cool the reaction solution to room temperature, reduce The solvent was distilled off under high pressure, and the residue was separated through a silica gel column (dichloromethane / methanol=50 / 1, V / V) to obtain the product Pid-Aze as an orange solid 0.11 g with a yield of 87%.

[0061] Its nuclear magnetic spectrum hydrogen spectrum data are as follows:

[0062] 1 H NMR (400MHz, CDCl 3 , ppm): δ=8.55(d, J=6.9Hz, 1H), 8.39(d, J=8.3Hz, 1H), 8.26(d, J=8.2Hz, 1H), 7.52(t, J=7.6Hz ,1H),6.41(d,J=8.3Hz,1H),4.51(t,J=6.9Hz,4H),3.12(t,J=7.2Hz,4H),2.61-2.52(m,2H),1.86 (m,4H),1.52(m,2H).

[0063] After testing, its structure is shown in the above formula Pid-Aze. Its ultraviolet absorption in ethanol is 450nm, and its fluorescence e...

Embodiment 3

[0065] The synthesis route and product structure of nuclear probe Pia-Aze are as follows:

[0066]

[0067] Weigh Naph-Aze (0.1g, 0.4mmol) in 5mL of absolute ethanol, add 1-(2-aminoethyl)piperazine (0.025g, 0.4mmol), heat the reaction solution to 80°C for 8h, The reaction solution was cooled to room temperature, and the solvent was distilled off under reduced pressure. The residue was separated through a silica gel column (dichloromethane / methanol=50 / 1, V / V) to obtain the product Pia-Aze as an orange solid 0.09 g, with a yield of 63%.

[0068] Its nuclear magnetic spectrum hydrogen spectrum data are as follows:

[0069] 1 H NMR (400MHz, CDCl 3 , ppm): δ=8.55(d, J=6.9Hz, 1H), 8.39(d, J=8.3Hz, 1H), 8.26(d, J=8.2Hz, 1H), 7.52(t, J=7.6Hz ,1H),6.41(d,J=8.3Hz,1H),4.51(t,J=6.9Hz,4H),4.32(d,J=6.1Hz,2H),3.70(s,4H),2.70(s ,2H),2.65-2.39(m,6H).

[0070] Its nuclear magnetic spectrum carbon spectrum data are as follows:

[0071] 13 C NMR (101MHz, CDCl 3 , ppm): δ=164.70, 163.98...

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Abstract

The invention provides a cell nucleus fluorescent probe with high brightness and high light stability. The probe is 4-substituted naphthalimide dye capable of being used for cell nucleus fluorescenceimaging, and the dye has the advantages of being low in synthetic raw material cost, simple in method, easy to derive and the like. Researches show that an azetidine structure is introduced to the 4-position of a naphthalimide parent in the dye so that rigidity and planarity of the dye are improved, a TICT process is effectively inhibited, the molar extinction coefficient of the dye in ethyl alcohol is about 15,000 M<-1>cm<-1>, the fluorescence quantum yield is about 0.6, and the dye has very high brightness and light stability. Basic groups such as morpholine rings, N,N-dimethyl and the likeare introduced into the dye, so that the dye can target cell nucleuses, and accurate positioning of cells is realized. The cell nucleus dye has very high brightness and light stability, and can be used for rapidly marking cell nucleuses and applied to the fields of cell nucleus fluorescence imaging and the like.

Description

technical field [0001] The invention belongs to the technical field of fluorescence imaging, and specifically relates to a class of high-brightness, high-light-stability cell nucleus fluorescent probes. Background technique [0002] Fluorescence imaging technology is one of the powerful tools in the field of modern life sciences, and the emergence of super-resolution imaging technology has pushed fluorescence imaging technology to a new level. Dyes with higher brightness and photostability are one of the necessary conditions for high-resolution imaging. Unfortunately, most of the existing fluorescent dyes lack sufficient brightness and photostability for super-resolution imaging. Naphthalimide dyes are typical push-pull electron system dyes. The introduction of electron-donating groups such as N,N-dimethyl at its 4-position can cause a significant red shift in the emission wavelength, but at the same time, the N, The N-dimethyl structure will also make the molecule easy to ...

Claims

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Application Information

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IPC IPC(8): C09B57/08C09K11/06G01N21/64
CPCC09B57/08C09K11/06C09K2211/1029C09K2211/1033C09K2211/1044G01N21/6428
Inventor 徐兆超乔庆龙
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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