High-efficiency Golgi apparatus targeting compound and biological application thereof

A technology of aggregation-induced luminescence and Golgi apparatus, which is applied in the field of tumor treatment and biological analysis and detection, and achieves the effect of inhibiting tumor growth, broad application prospects and low cytotoxicity

Active Publication Date: 2021-11-23
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few reports on compounds that can target the Golgi apparatus, especially AIE-based compounds that can target the Golgi apparatus

Method used

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  • High-efficiency Golgi apparatus targeting compound and biological application thereof
  • High-efficiency Golgi apparatus targeting compound and biological application thereof
  • High-efficiency Golgi apparatus targeting compound and biological application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1: Preparation of compound TPE-PyT-PS (without cyano group in the electron-withdrawing group)

[0041]

[0042] Synthesis of compound 1: in N 2 In the atmosphere, add 1,6-dibromopyrene (5.0g, 13.90mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxybenzaldehyde -2-yl)thiophene-2-amino formaldehyde (3.33g, 14.0mmol) and anhydrous potassium carbonate (4.14g), and add 90ml toluene and 15ml water to this system and carry out deoxygenation treatment, add four (three Phenylphosphine) palladium catalyst (0.81 g, 0.70 mmol). The reaction mixture was reacted at 85°C for 18h, and the progress of the reaction was tracked with a TLC plate. After the reaction was completed, the reaction liquid was cooled to room temperature, and the obtained crude product was extracted with water and dichloromethane, and then the solvent was distilled off under reduced pressure. The crude product was subjected to column chromatography using dichloromethane and petroleum ether (DCM:petroleum et...

Embodiment 2

[0045] Embodiment 2: the preparation of compound TPE-PyT-CPS

[0046]

[0047] Synthesis of compound TPE-PyT-CP: under nitrogen protection, compound 2 (147mg, 0.228mmol) and 2-(pyridin-4-yl) acetonitrile (34mg, 0.228mmol) were added in a 50ml two-necked flask, and then added 15ml of ethanol and 4 drops of piperidine. The mixture was heated to 80°C and stirred for 24 hours. After the reaction, it was extracted with dichloromethane and water, and then dried over anhydrous magnesium sulfate. Column separation with DCM (R f =0.4) crude product, 120 mg of red solid was obtained, yield 65.3%. 1 H NMR (400MHz, Chloroform-d) δ8.72(d, J=5.5Hz, 2H), 8.48(d, J=9.2Hz, 1H), 8.27–8.18(m,3H), 8.18–8.12(m, 2H), 8.07–7.99(m, 3H), 7.94(d, J=3.8Hz, 1H), 7.76(d, J=5.0Hz, 2H), 7.55(d, J=3.8Hz, 1H), 7.38( d,J=8.1Hz,2H),7.25–7.13(m,7H),7.07(d,J=8.8Hz,2H),7.01(d,J=8.6Hz,2H),6.75(d,J=8.8 Hz,2H),6.68(d,J=8.7Hz,2H),3.81(s,3H),3.77(s,3H). 13 CNMR(101MHz,Chloroform-d)δ158.27,158.15,148.72,148.71...

Embodiment 3

[0049] Embodiment 3: the preparation of compound HTPA-PyT-CPS

[0050]

[0051] Synthesis of compound 4: in N 2 In the atmosphere, 1-bromooctane (1.93g, 10.0mmol), 4,4'-((4-bromophenyl)azynyl)diphenol (1.89g, 5.07mmol) and Anhydrous potassium carbonate (2.1g, 15mmol), and 90ml DMF was added to the system for deoxygenation treatment, the reaction mixture solution was reacted at 140°C for 18h, and the reaction progress was tracked with a TLC plate. After the reaction was completed, the reaction liquid was cooled to room temperature, and the obtained crude product was extracted with water and dichloromethane, and then the solvent was distilled off under reduced pressure. The crude product was separated by column chromatography using dichloromethane and petroleum ether (DCM:petroleum ether=1:6) to obtain product 4 (2.52 g, 87.1%). 1 H NMR (400MHz, Chloroform-d) δ7.22 (d, J = 8.9Hz, 2H), 7.00 (d, J = 8.6Hz, 4H), 6.90–6.68 (m, 6H), 3.92 (t, J = 6.5Hz, 4H), 1.77(dt, J=14.5, 6.6...

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Abstract

The invention discloses a high-efficiency Golgi apparatus targeting compound and biological application thereof, and the compound has the following general formula structure, wherein R1 represents an electron withdrawing group selected from one or more of electron withdrawing groups, R2 represents a substituted/substituted electron donating group in which one or multiple sites of one or more benzene rings is/are substituted by H or R3, R3 represents C1-C12 alkyl, C1-C12 alkoxy or C1-C12 fluoroalkoxy, and when the the sites are substituted by a plurality of R3 , the substituent groups are the same or different. The compound based on aggregation-induced emission can effectively target Golgi apparatus, is used for tumor treatment or cell imaging, and is especially used for cell/tissue/living tumor treatment.

Description

technical field [0001] The invention belongs to the field of tumor treatment and biological analysis and detection, and relates to a compound based on aggregation-induced luminescence, in particular to a compound and biological application for efficiently targeting the Golgi apparatus. Background technique [0002] So far, cancer is considered to be the second largest killer threatening human health. The United Nations Cancer Agency recently pointed out that by 2030, more than 13 million patients will die of cancer every year. At present, the means of treating cancer mainly include surgery, radiotherapy, chemotherapy and molecular targeted drugs. Among them, surgery and radiotherapy are local treatments, while chemotherapy and molecular targeted drug therapy are systemic treatments. Among chemotherapy drugs, the clinical utilization rate of platinum drugs exceeds 50%. However, platinum-based antineoplastic drugs have serious side effects in clinical use, such as nephrotox...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/06C09K11/06A61K41/00A61P35/00G01N21/64
CPCC07D409/06C09K11/06A61K41/0057A61P35/00G01N21/6428C09K2211/1011C09K2211/1007C09K2211/1014C09K2211/1029C09K2211/1092
Inventor 郭子建何卫江陈韵聪刘明伦
Owner NANJING UNIV
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