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Quinoline iridium complex targeting lung cancer cis-platinum drug-resistant cells as well as synthesis method and application thereof

A technology of drug-resistant cells and synthesis method, applied in the field of medicine, can solve the problems of synthesis of metal iridium complexes that have not been reported and the like

Active Publication Date: 2021-10-22
YULIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0003] In addition, a large number of 8-hydroxyquinoline metal complexes have been reported (Q.-P.Qin, et al.Eur.J.Med.Chem., 2020, 192, 112192.), but with 4 / 5-bromo- 8-Hydroxyquinoline and 2-phenylquinoline as mixed ligands to synthesize metal iridium complexes have never been reported

Method used

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  • Quinoline iridium complex targeting lung cancer cis-platinum drug-resistant cells as well as synthesis method and application thereof
  • Quinoline iridium complex targeting lung cancer cis-platinum drug-resistant cells as well as synthesis method and application thereof
  • Quinoline iridium complex targeting lung cancer cis-platinum drug-resistant cells as well as synthesis method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] In a high-temperature pressure-resistant tube with a volume of 25.0 mL, add 0.1 mmol of iridium dimer [Ir(2pq) 2 Cl] 2 And 0.2mmol 4-bromo-8-hydroxyquinoline (4Br) or 5-bromo-8-hydroxyquinoline (5Br), after mixing, add dropwise 3.0mL methanol and 0.2mL dichloromethane, under sealed conditions, heat to 100°C, reacted for 48.0h, precipitated reddish-brown bulk crystals or reddish-brown powder, filtered, and dried in a vacuum oven at 55°C to obtain the target complexes 4BrIr and 5BrIr with yields of 73.5% and 82.3%.

[0034] Identification of the resulting complexes 4BrIr and 5BrIr:

[0035] (1) The electrospray mass spectrogram of complex 4BrIr and 5BrIr, its spectrogram is as figure 2 with 3 , where M is the molecular weight of each complex.

[0036] Complex 4BrIr: ESI-MS m / z:776.05[M-(phq)+2(DMSO)] + ;

[0037] Complex 5BrIr: ESI-MS m / z:776.05[M+H] + .

[0038] (2) The single crystal structure diagram of the complex, such as Figure 4 shown.

[0039] (3) The ...

Embodiment 2

[0047] In a high-temperature pressure-resistant tube with a volume of 25.0 mL, add 0.1 mmol of iridium dimer [Ir(2pq) 2 Cl] 2 And 0.2mmol 4-bromo-8-hydroxyquinoline (4Br) or 5-bromo-8-hydroxyquinoline (5Br), after mixing, add 1.0mL methanol and 5.5mL dichloromethane dropwise, under sealed conditions, heat Reaction at 100°C for 48.0 hours, reddish-brown massive crystals or reddish-brown powder precipitated, filtered, and dried in a vacuum oven at 55°C to obtain the target complexes 4BrIr and 5BrIr with yields of 76.2% and 80.9%.

Embodiment 3

[0049] In a high-temperature pressure-resistant tube with a volume of 25.0 mL, add 0.1 mmol of iridium dimer [Ir(2pq) 2 Cl] 2 And 0.2mmol 4-bromo-8-hydroxyquinoline (4Br) or 5-bromo-8-hydroxyquinoline (5Br), after mixing, add 1.0mL methanol and 1.0mL dichloromethane dropwise, under sealed conditions, heat to 100°C, reacted for 48.0h, precipitated reddish-brown massive crystals or reddish-brown powder, filtered, and dried in a vacuum oven at 55°C to obtain the target complexes 4BrIr and 5BrIr with yields of 74.9% and 80.1%.

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Abstract

The invention discloses a quinoline iridium complex targeting lung cancer cis-platinum drug-resistant cells as well as a synthesis method and application thereof, belongs to the field of medicines, and mainly solves the technical problem of drug resistance of lung cancer cis-platinum drugs in the prior art. The method specifically comprises the following steps: (1) adding an iridium dimer [Ir(2pq)2Cl]2 and 4-bromine-8-hydroxyquine or 5-bromine-8-hydroxyquinoline into a polar solvent to obtain a mixed solution; (2) reacting the obtained mixed solution at 100 DEG C under a sealed condition to obtain a precipitate; and (3) filtering and drying the precipitate to obtain the target complex. Research finds that the complexes 4BrIr and 5BrIr inhibit the growth of A549 / DDP in a targeted manner, the IC50 values of the complexes are 0.53 + / -0.11 [mu]M and 0.09 + / -0.03 [mu]M respectively, and the in-vitro anti-lung cancer activity of the complexes is far greater than that of 4Br and 5Br ligands, so that the complexes are targeted to lung cancer and overcome the drug resistance of cis-platinum. In-vivo anti-cancer research finds that the in-vivo anti-cancer inhibition effect of the compound reaches 43.5% and is higher than that of cis-platinum drugs, and the compound has potential medicinal value and is expected to be used for preparing various anti-lung cancer drugs.

Description

technical field [0001] The invention relates to the technical field of medicine, more specifically, it relates to a quinoline-iridium complex targeting lung cancer cisplatin-resistant cells and a synthesis method thereof. The invention also relates to the application of a quinoline-iridium complex targeting cisplatin-resistant cells of lung cancer in the preparation of anti-lung cancer drugs. Background technique [0002] Lung cancer is one of the most common malignant tumors in the world, and it ranks first among cancers because of its high mortality rate and clinical refractory nature. At present, the number of drug-resistant cases in cisplatin therapy for lung cancer worldwide is increasing, which seriously threatens the lives and health of patients. The iridium complex not only has excellent photophysical properties, but also is very sensitive to the tumor microenvironment, and is suitable for the construction of tumor-responsive targeting materials or anticancer drugs....

Claims

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Application Information

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IPC IPC(8): C07F15/00A61P35/00
CPCC07F15/0046A61P35/00
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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