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A bisquinoline iridium complex for treating cisplatin-resistant cancer cells and its preparation method and application

A technology of bisquinoline iridium, cancer cells, applied in the field of medicine

Active Publication Date: 2022-05-20
YULIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the iridium complexes of 8-hydroxyquinoline and 1-phenylpyrazole derivatives have been reported to have a good inhibitory effect on cervical cancer HeLa and ovarian cancer cisplatin-resistant cells SK-OV-3 / DDP, and target Mitochondrial membrane of cervical cancer HeLa (Q.-P.Qin, et al. European Journal of Medicinal Chemistry, 2020, 192, 112192.), but with 8-hydroxyquinoline derivatives and 2-phenylquinoline as mixed complexes body, the synthesis of metal iridium complexes has not been reported

Method used

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  • A bisquinoline iridium complex for treating cisplatin-resistant cancer cells and its preparation method and application
  • A bisquinoline iridium complex for treating cisplatin-resistant cancer cells and its preparation method and application
  • A bisquinoline iridium complex for treating cisplatin-resistant cancer cells and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0042] The preparation method of the bisquinoline iridium complex for treating cisplatin-resistant cancer cells is as follows:

[0043] (1) The iridium dimer [Ir(2pq) 2 Cl] 2 and ligand 8-hydroxyquinoline derivatives (1a-1f), added in a polar solvent to obtain a mixed solution;

[0044] (2) Reacting the obtained mixed solution at 90° C. for 48 hours under sealed conditions to obtain a precipitate;

[0045] (3) The precipitate was filtered and dried to obtain the target complexes 2a-2f with a yield of 78.2-91.6%.

[0046] In step (1), the iridium dimer [Ir(2pq) 2 Cl] 2 The molar ratio of the ligand to the 8-hydroxyquinoline derivative (1a–1f) is 1:2.

[0047] 8-Hydroxyquinoline derivatives (1a–1f) ligands include 5,7-diiodo-8-hydroxyquinoline (1a), 5,7-dichloro-8-hydroxyquinoline (1b), 5-chloro -7-iodo-8-hydroxyquinoline (1c), 5,7-dibromo-8-hydroxyquinoline (1d), 5,7-dichloro-2-methyl-8-hydroxyquinoline (1e) and 5,7-dibromo-2-methyl-8-hydroxyquinoline (1f).

[0048] In st...

Embodiment 2

[0068] The difference from Example 1 is that in the step (2), the solvent is added dropwise with 0.5 mL of dichloromethane and 5.5 mL of ethanol, and the yield is 79.9-90.0%.

Embodiment 3

[0070] The difference from Example 1 is that in the step (2), the solvent added dropwise is a mixed solution of 1.5 mL of dichloromethane and 2.5 mL of methanol-ethanol, and the yield is 81.2-91.1%.

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Abstract

The invention discloses a bisquinoline iridium complex for treating cisplatin-resistant cancer cells and its preparation method and application, which belongs to the field of medicine and aims to solve the technical problem of lung cancer cisplatin drug resistance in the prior art , the method is specifically as follows: (1) the iridium dimer [Ir(2pq) 2 Cl] 2 Add the ligand 8-hydroxyquinoline derivatives into a polar solvent to obtain a mixed solution; (2) react the obtained mixed solution under sealed conditions at 90°C to obtain a precipitate; (3) dissolve the precipitate Filter and dry to obtain the target complex. The study found that the complex 2a‑2f has a good inhibitory effect on A549 / DDP and SK‑OV‑3 / DDP, and its IC 50 The value is 0.11‑1.83 μM, its antitumor activity in vitro is much greater than that of 1a‑1f ligand and clinical anticancer drug cisplatin, and its toxicity to normal cells HL‑7702 is very small, indicating that they target tumors and overcome the inhibition of cisplatin drug resistance. In vivo anti-cancer studies have found that its anti-cancer inhibitory effect in vivo reaches 64.1%, which has potential medicinal value and is expected to be used in the preparation of various anti-tumor drugs.

Description

technical field [0001] The invention relates to the technical field of medicine, more specifically, it relates to a bisquinoline-iridium complex for treating cisplatin-resistant cancer cells and its preparation method and application. Background technique [0002] Cisplatin drugs are one of the most commonly used chemotherapeutic drugs in clinical treatment, and have obvious curative effects on the treatment of various cancers, but their drug resistance limits their further clinical use; in addition, metal iridium complexes have Phosphorescence has a long lifetime and a large Stokes shift, and has been widely used in the fields of fluorescent probes, bioimaging, and anticancer. In view of its own characteristics, iridium complexes have great prospects as a metal antitumor drug. Therefore, there is an urgent need to design anticancer iridium complexes that target tumors and overcome cisplatin-like drug resistance. [0003] At present, the iridium complexes of 8-hydroxyquinol...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00A61K31/555A61P35/00
CPCC07F15/0033A61P35/00
Inventor 杨燕覃其品谢秋季潘凤华甘雨覃芳香梁晓敏冯清丽龙鸿敏李威陈志林
Owner YULIN NORMAL UNIVERSITY
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