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Two-photon polar fluorescent probe based on carbazole and preparation method and application of two-photon polar fluorescent probe

A fluorescent probe, two-photon technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve rare problems and achieve the effects of easy synthesis, good lysosome positioning ability, and good cell permeability

Active Publication Date: 2019-07-12
ANHUI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there are very few literature reports on the use of two-photon polar fluorescent probes with carbazole as fluorophore for monitoring lysosome polarity during apoptosis

Method used

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  • Two-photon polar fluorescent probe based on carbazole and preparation method and application of two-photon polar fluorescent probe
  • Two-photon polar fluorescent probe based on carbazole and preparation method and application of two-photon polar fluorescent probe
  • Two-photon polar fluorescent probe based on carbazole and preparation method and application of two-photon polar fluorescent probe

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Experimental program
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Embodiment 1

[0034] Embodiment 1: the synthesis of compound 1

[0035] In a 500mL round bottom flask, KOH (260mmol, 14.63g) was dissolved in an appropriate amount of acetone (200mL), stirred at room temperature for 30 minutes, and then 3-bromocarbazole (52mmol, 2.80g) dissolved in acetone was added to the above solution , stirred at room temperature for 4 hours, finally slowly added bromoethane (78mmol, 6mL) dissolved in acetone, stirred overnight at room temperature, filtered off the KOH solid after the reaction was completed, and spin-dried with a rotary evaporator. Methane chloride was dissolved, silica gel sample preparation, column chromatography separation, using petroleum ether:dichloromethane (PE:DCM, v / v, 50:1) as eluent, purified to obtain compound 1, white flocculent solid, product: 11.12 g, yield: 78%. 1 H NMR (400MHz, DMSO-d 6 ,ppm)δ8.40(d,J=1.5Hz,1H),8.21(d,J=7.7Hz,1H),7.65–7.54(m,3H),7.49(ddd,J=8.3,7.2,1.2Hz ,1H),7.25–7.18(m,1H),4.44(q,J=7.1Hz,2H),1.30(t,J=7.1Hz,3H). 13 ...

Embodiment 2

[0036] Embodiment 2: the synthesis of compound 2

[0037] use CH 2 Cl 2 Dissolve compound 1 (33mmol, 9.05g) in 500mL round bottom flask, under the state of stirring, add AlCl rapidly 3 (72.2mmol, 9.63g), then cooled to 0 ° C, and then CH 2 Cl 2 Dissolved acetic anhydride (36mmol, 3.68g) was added dropwise to the above solution, and for about ten minutes, the stirring was increased, and the ice-salt bath device was removed, and the room temperature was reacted overnight. 2 Add O and HCl to the mixed solution and extract with dichloromethane for more than two times, and then use 1mol / L NaHCO 3 The aqueous solution was washed with water, followed by extraction with water and dichloromethane twice. Anhydrous MgSO for organic phase 4 Dry and filter again, remove the organic solvent by a rotary evaporator, dissolve the remaining solid with an appropriate amount of dichloromethane, prepare a sample on silica gel, separate by column chromatography, and use petroleum ether: ethyl...

Embodiment 3

[0038] Embodiment 3: the synthesis of compound 3

[0039] Weigh compound 2 (10mmol, 3.162g) and potassium tert-butoxide (10mmol, 1.12g) in a 250mL round bottom flask, add an appropriate amount of tetrahydrofuran (100mL) to dissolve, stir well at room temperature, and slowly Diphenylamino-4-benzaldehyde (12mmol, 3.28g) dissolved in tetrahydrofuran was added dropwise. After the dropwise addition, the temperature was set at 50°C and the reaction was carried out overnight. After the reaction was completed, the tetrahydrofuran was removed with a rotary evaporator, and the remaining mixture was Extract with dichloromethane and water three times to remove inorganic salts, collect the organic phase, and use anhydrous MgSO 4 Dry and filter again, remove the organic solvent by a rotary evaporator, dissolve the remaining solid with an appropriate amount of dichloromethane, prepare a sample on silica gel, separate by column chromatography, use petroleum ether: ethyl acetate (PE: EA, v / v, ...

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Abstract

The invention discloses a two-photon polar fluorescent probe based on carbazole and a preparation method and application of the two-photon polar fluorescent probe. The structure of the two-photon polar fluorescent probe based on the carbazole is shown in the description. The fluorescent quantum yield and the fluorescent lifetime of the two-photon polar fluorescent probe have a good linear relationship on polar response. Besides, fluorescent probe moleculars have an excellent two-photon absorption function. Through a cytotoxicity test, it is shown that the probe has little side and toxic effects on HeLa cells; through a two-photon confocal imaging experiment, it is shown that the probe has good lysosome localization capacity and cell permeability, is high in light stability and suitable forlong-time real-time two-photon fluorescence imaging and visualization research of changes in cell lysosome polarity.

Description

technical field [0001] The invention relates to a two-photon fluorescent probe and its preparation method and application, in particular to a carbazole-based two-photon polar fluorescent probe and its preparation method and application. Background technique [0002] Polarity is an important parameter in chemistry and biology. In chemistry, polarity is a key parameter affecting chemical reactions. In the field of biology, the polarity of cells is a feedback of cellular operating and regulatory mechanisms, and many cellular events, such as adipogenic differentiation, activation of immune responses, cell migration and death, and transport of molecules across cell layers, can lead to changes in cell polarity. Mutations. Therefore, abnormal changes in polarity are highly correlated with biological disorders and diseases (eg, diabetes, liver cirrhosis, etc.). In addition, the polarity of different regions of the cell is different, and the polarity of each subcellular organelle ...

Claims

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Application Information

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IPC IPC(8): C07D401/06C09K11/06G01N21/64
CPCC07D401/06C09K11/06C09K2211/1007C09K2211/1014C09K2211/1029G01N21/6428
Inventor 冯燕陈晓华方国顺丁志强李认认张虎
Owner ANHUI UNIVERSITY
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