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Mitochondrial targeting compound with aggregation-induced emission property and synthesis method and application thereof

A technology of aggregation-induced luminescence and synthesis method, applied in the field of synthesis of the above-mentioned compounds, can solve the problems of high drug resistance, strong nephrotoxicity and neurotoxicity, low selectivity of target DNA, etc., and achieves low toxicity and side effects, high anti-cancer Activity, the effect of inhibiting proliferation

Active Publication Date: 2022-01-21
NANJING NORMAL UNIVERSITY
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  • Abstract
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AI Technical Summary

Problems solved by technology

Metallic antineoplastic drugs are important members of chemotherapy drugs, but they still have some disadvantages, including high incidence of drug resistance, strong nephrotoxicity and neurotoxicity, and low selectivity to target DNA, etc.

Method used

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  • Mitochondrial targeting compound with aggregation-induced emission property and synthesis method and application thereof
  • Mitochondrial targeting compound with aggregation-induced emission property and synthesis method and application thereof
  • Mitochondrial targeting compound with aggregation-induced emission property and synthesis method and application thereof

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Embodiment 1

[0034] Mitochondrial targeting compound (DP-PPh) with aggregation-induced luminescent properties of the present invention 3 ) is synthesized by the following method:

[0035] (1) Under the protective atmosphere of argon, the Pd(OAc) 2 (23mg, 0.1mmol), t-BuONa (0.58g, 6.0mmol), (t-Bu) 3 PHBF 4 (88mg, 0.3mmol), bromopyridinephenol (1.25g, 5.0mmol), dimethyldihydropropidine (DMAC, 1.25g, 6.0mmol) and toluene (25mL) were added to a 100mL round bottom flask (the above reaction system In, Pd(OAc) 2 , t-BuONa and (t-Bu) 3 PHBF 4 catalyst); heated to 60°C, stirred at reflux for 48h, cooled to room temperature after the reaction was completed, poured the reactant into water, extracted with 50mL×3 dichloromethane, and dissolved in anhydrous Na 2 SO 4 After removing the solvent, the crude product was subjected to silica gel column chromatography, using DCM / ethyl acetate (20:1v / v) as the eluent to obtain a yellow solid lutidine phenol (DP-OH), and the solid was collected. Vacuum d...

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Abstract

The invention discloses a mitochondrial targeting compound with aggregation-induced emission property, according to the compound, fluorescent small molecules with aggregation-induced emission property are combined with mitochondrial targeting groups to obtain a product with high anticancer activity and low toxic and side effects; the compound has good cell uptake capability and capability of targeting mitochondria in tumor cells; secondly, the compound realizes good anti-tumor activity by inhibiting proliferation of human-derived tumor cells, inducing generation of active oxygen in cancer cells, reducing mitochondrial membrane potential, changing mitochondrial morphology, damaging mitochondrial functions and inducing autophagy of tumor cells (mitochondria); the action mechanism of the compound is different from the action mechanism of a metal anti-tumor drug, so that the problem of drug resistance cannot be generated in the anti-tumor process by using the compound, and a continuous and good anti-tumor effect is ensured; finally, the compound can effectively inhibit the proliferation of tumor cells which have drug resistance to the metal antitumor drug (cisplatin), so that the problem that the existing chemotherapeutic drug cannot effectively overcome the drug resistance of the tumor cells (cisplatin) is solved.

Description

technical field [0001] The present invention relates to a mitochondria-targeting compound with aggregation-induced luminescent properties, and also relates to a synthesis method and application of the compound. [0002] technical background [0003] Cancer is one of the deadliest diseases worldwide. According to the latest global cancer data for 2020 released by the World Health Organization's International Agency for Research on Cancer (IARC), the number of new cancer cases in China far exceeds that of other countries in the world. Traditional cancer treatments include surgery, radiation therapy and chemotherapy. Metallic antineoplastic drugs are important members of chemotherapy drugs, but they still have some disadvantages, including high incidence of drug resistance, strong nephrotoxicity and neurotoxicity, and low selectivity to target DNA. [0004] AIE (Aggregation-induced emission) was first proposed in 2001 by Academician Tang Benzhong of the Hong Kong University of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6558C09K11/06A61P35/00
CPCC07F9/65583C09K11/06A61P35/00C09K2211/1014C09K2211/1029
Inventor 苏志林海苏岩王萌萌
Owner NANJING NORMAL UNIVERSITY
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