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Quinone type electron withdrawing group type compound, preparation method and applications thereof

A technology of electron-withdrawing groups and electron-donating groups, which is applied in the field of compounds based on quinone-type electron-withdrawing groups and their preparation, and can solve the problems of low stability, high preparation cost of commercially labeled probes, high self-absorption, etc. question

Active Publication Date: 2020-02-28
HKUST SHENZHEN RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to provide a compound based on quinone-type electron-withdrawing group and its preparation method and application, to solve the problems of red light and near-infrared in the prior art Insufficient probes and high preparation costs, high self-absorption, low stability, and low sensitivity of commercially labeled probes

Method used

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  • Quinone type electron withdrawing group type compound, preparation method and applications thereof
  • Quinone type electron withdrawing group type compound, preparation method and applications thereof
  • Quinone type electron withdrawing group type compound, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0120] Embodiment 1: the preparation of product

[0121] (1) Synthesis of 2TPE-BI

[0122]Add 4,7-dibromo-spiro[benzo[d]imidazole-2,1'-cyclohexane](Br-BI-Br; 1.00g, 2.91mmol), Tributyl(4-(1,2,2-triphenylvinyl)phenyl)stannane, TPE-SnBu 3 ; 3.62g, 5.82mmol), ditriphenylphosphine palladium dichloride (Pd(PPh 3 ) 2 Cl 2 ; 0.25g, 0.35mmol) and anhydrous and oxygen-free dimethylformamide (DMF; 20mL) solvent, refluxed and stirred for 24 hours. After the reaction mixture was placed in a reduced pressure environment to remove the solvent, the orange-red 2TPE-BI product (0.64 g) was obtained by column purification with a yield of 26%. 1 H NMR (400MHz, CDCl 3 ),δ(ppm):7.80-7.78(m,4H),7.23(s,2H),7.13-7.03(m,34H),1.95(m,4H),1.75-1.66(m,6H). 13 C NMR (100MHz, CDCl 3 ,δ):159.22,144.05,143.90,143.83,143.82,141.49,140.75,134.78,134.38,131.60,131.58,131.51,131.48,130.86,127.94,127.83,127.76,127.61,126.69,126.63,126.58,107.53,33.30, 25.95,25.07.HRMS(MALDI-TOF)m / z:[M] + calculated for C...

Embodiment 2

[0131] Example 2: Research on Optical and Aggregation-Induced Luminescent Properties of Products

[0132] Taking three quinone-type electron-withdrawing group fluorescent products 2TPA-BI, 2TPA-T-BI and 2TPA-2T-BI as examples to illustrate their optical properties and aggregation-induced luminescent properties. The same is true for other products, and details will not be repeated here.

[0133] (1) Research on optical properties and thermal stability

[0134] The ultraviolet-visible (UV-vis) absorption spectrum and photoluminescence (PL) spectrum of 2TPA-BI, 2TPA-T-BI and 2TPA-2T-BI in tetrahydrofuran (THF) solution are as follows Figure 2-4 shown. The maximum absorption wavelengths of the three products in THF solution are 470, 515 and 563nm, the emission wavelengths are 590, 630 and 677nm respectively, and the Stokes shifts are 120nm (2TPA-BI), 115nm (2TPA-T -BI) and 144nm (2TPA-2T-BI), the characteristics of the large Stokes shift and long wavelength emission, as the pr...

Embodiment 3

[0145] Example 3: Application of the product in in vitro cancer cell and in vivo tumor tissue labeling and imaging

[0146] (1) Preparation of aggregation-induced emission nanoparticles (AIE dots)

[0147] like Figure 27 As shown, the 2TPE-2T-BI product that can emit near-infrared light, the amphoteric compound DSPE-PEG, and the DSPE-PEG-DBCO molecule with a bioorthogonal DBCO functional group were mixed in phosphate buffered saline (PBS ) environment for nanoprecipitation to obtain DBCO-AIEdots nanoparticles with bioorthogonal reaction capability. like Figure 28 As shown, the absorption and emission wavelengths of DBCO-AIEdots nanoprobes extend from 572 and 710 nm to the near-infrared region, respectively, and its maximum Stokes shift is 138 nm. In addition, if Figure 29-30 As shown, the particle size of DBCO-AIEdots nanoparticles is between 85 nm, which is quite suitable for blood circulation process of in vivo labeling and imaging.

[0148] (2) Cell culture

[0149...

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Abstract

The invention relates to a quinone type electron withdrawing group type compound, a preparation method and applications thereof. According to the invention, a series of quinone type electron withdrawing group type compounds synthesized by the method have good aggregation-induced emission characteristics; and a probe of aggregation-induced emission type nanoparticles is formed through coating by matching the quinone type electron withdrawing group type compound, an amphoteric compound and a bioorthogonal reaction functional group, and can be used for specifically marking and imaging cancer cells or tumors in vitro or in vivo, so important significance and value is provided in promoting of the fields of bioluminescence detection technology and biomedicine.

Description

technical field [0001] The invention relates to the technical field of detection and analysis, in particular to a compound based on a quinone electron-withdrawing group and its preparation method and application. Background technique [0002] In recent years, adjusting the absorption and emission spectra of different luminescent chromophores through the combination of electron-donating groups and electron-withdrawing groups has been a widely used strategy for designing materials, developing new electron-donating groups or electron-withdrawing groups. Missions have always been the most important and critical research. [0003] AIE luminescent materials (AIE molecule, AIE fluorophore, AIEgen) hardly emit light in solution, and the light emission is enhanced in solid state or aggregated state. The main theoretical basis for the design strategy of its structure is the restricted intramolecular motion (RIM) mechanism model. That is, the intramolecular motion causes the energy of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/02C07D409/04C07D409/14G01N21/64C09K11/06A61K49/00
CPCC07D235/02C07D409/04C07D409/14G01N21/6428C09K11/06A61K49/0021G01N2021/6439C09K2211/1044C09K2211/1092C09K2211/1007C09K2211/1014
Inventor 唐本忠倪侦翔张鹏飞林荣业
Owner HKUST SHENZHEN RES INST
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