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Carbene imine semi-sandwich iridium complex capable of targeting lysosome as well as preparation method and application thereof

A technology of carbene imine and iridium complex, which is applied in the field of chemical pharmaceuticals and can solve problems such as strong cytotoxicity

Active Publication Date: 2018-08-14
QUFU NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The non-platinum anti-tumor metal complexes that are widely studied today include metal compounds such as Ru, Ir, Fe, Au, Ga, Os, etc., because they are different from the anti-tumor mechanism of platinum drugs, so they can overcome the resistance of platinum drugs. Drug properties, thus showing good application prospects, Liu Zhe et al. synthesized pentamethylcyclopentadienyl Ir with dicarbene ligands and imine pyridine ligands III Organometallic complexes, ( Dalton Trans, 2017, 46 (21) :6870-6883 ), ( Dalton Trans., 2017, 46, 15520–15534 ), showing anti-tumor activity, however, when the pyridine of the iminopyridine ligand is replaced by imidazole, and the other structures are the same, the complex with the carbene imine ligand shows more strong cytotoxicity

Method used

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  • Carbene imine semi-sandwich iridium complex capable of targeting lysosome as well as preparation method and application thereof
  • Carbene imine semi-sandwich iridium complex capable of targeting lysosome as well as preparation method and application thereof
  • Carbene imine semi-sandwich iridium complex capable of targeting lysosome as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] Weigh 0.5 g IrCl 3 ·nH 2 6 parts of O were added to 6 inner tanks of the microwave digestion apparatus, and 0.75 mL of 1,2,3,4,5-pentamethylcyclopentadiene and 20 mL of methanol were added to each tank, ultrasonicated, nitrogen gas was applied, and the tanks were covered Cover, assemble the main tank and the standard tank, set the parameters of the microwave digestion instrument (the specific parameters are shown in Table 1, the same below), and react with the microwave digestion instrument. The obtained red solid product is dissolved in dichloromethane and filtered through diatomaceous earth. Remove unreacted IrCl 3 ·nH 2 O, after that, recrystallized by dichloromethane / ether diffusion method to obtain orange-red iridium dimer (formula (III) R 1 = methyl) product, yield 53.3%. 1 H NMR (500.13 MHz, CDCl 3 ): δ 1.59 (s, J = 1.4 Hz, 15H).

[0070] Table 1

[0071]

Embodiment 2

[0073] Weigh 0.5 g IrCl 3 ·nH 2 6 parts of O were added to 6 inner tanks of the microwave digestion apparatus respectively, and 1.3 g of 1-biphenyl, 2,3,4,5-tetramethylcyclopentadiene, 20 mL of methanol were added to each tank, ultrasonicated, and nitrogen gas , cover the tank lid, assemble the main tank and the standard tank, set the parameters of the microwave digestion instrument, and react with the microwave digestion instrument. The red solid product obtained is dissolved in dichloromethane and filtered through diatomaceous earth to remove unreacted IrCl 3 ·nH 2 O, after that, recrystallized by dichloromethane / ether diffusion method to obtain orange-red iridium dimer (formula (III) R 1 = biphenyl) product, yield 18.7%. 1 H NMR (500 MHz, DMSO) δ 7.77–7.64 (m,6H), 7.48 (t, J = 7.6 Hz, 2H), 7.39 (t, J = 7.3 Hz, 1H), 1.72 (d, J = 14.7Hz , 12H).

Embodiment 3

[0075] 25.0 mg [3-Me-1-(2, 6-dimethylphenyl)iminyl-C 3 h 3 N 2 ] + Cl - and 26.4 mg Ag 2 O was placed in a 25 mL round bottom flask, stirred at room temperature for 6 h in the dark, and then filtered through celite to remove excess Ag 2 O, and wash the filter cake with dichloromethane, and pour the filtrate into a container containing 37.8 mg iridium dimer (formula (III) R 1 = methyl) in a round bottom flask, stirred overnight at room temperature, then added 103.2 mg KPF 6 Continue to stir for 30 min, hang the solvent to dryness with a rotary evaporator to obtain a yellow solid, dissolve the solid with dichloromethane, and filter with a 0.22 μm filter head to remove excess KPF 6 , with CH 2 Cl 2 / n-hexane recrystallization to obtain a yellow crystal product.

[0076] H NMR and mass spectrograms such as image 3 and Figure 15 Shown: 1 H NMR (500 MHz, CDCl 3 ) δ 7.61 (d, J =2.3 Hz, 1H), 7.29 (d, J = 2.3 Hz, 1H), 7.24 (dd, J = 6.2, 2.8 Hz, 1H), 7.22 –7.15 (m, ...

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Abstract

The invention relates to a metal compound, in particular to a carbene imine semi-sandwich iridium complex capable of targeting lysosome as well as a preparation method and application thereof, and belongs to the technical field of chemical pharmacy. The compound has a structure formula shown in the description. The prepared compound can be easily modified, can be modified in a plurality of positions, has good anticancer activity, and belongs to a novel kind of potential anticancer medicine. The condition that the semi-sandwich iridium complex can perform cell imaging through laser a co-focusing microscope is found for the first time; the problem of unclear targeting of the semi-sandwich compound is solved; a method for effectively studying the anticancer mechanism of the compound is provided; the cell imaging result shows that the compound can well target the lysosome.

Description

technical field [0001] The invention relates to metal complexes, in particular to a carbene imine semi-sandwich iridium complex capable of targeting lysosomes, a preparation method and application thereof, and belongs to the technical field of chemical pharmacy. Background technique [0002] Cancer will quickly become the number one killer in the world. According to the World Health Organization (WHO), it caused 8.8 million deaths in 2015. From a global perspective, nearly 1 / 6 of the deaths are caused by cancer. Due to the rapid increase of cancer cases worldwide, there is an indispensable need to develop and screen potential anticancer drugs. Cisplatin (PtCl), the representative of the first metal-based anticancer drug used in clinical 2 (NH 3 ) 2 , cisplatin) has limited its further clinical use due to its large toxic side effects, easy drug resistance and ineffectiveness for some tumor treatments. Therefore, searching for high-efficiency, low-toxicity, and broad-spect...

Claims

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Application Information

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IPC IPC(8): C07F15/00A61P35/00G01N21/63
CPCA61P35/00C07F15/0033G01N21/63
Inventor 郭丽华刘哲杨玉亮田珍珍巩玉腾郑红梅
Owner QUFU NORMAL UNIV
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