Semi-sandwich iridium complex having fluorescent property and containing N-N two-tooth chelated ligand, and preparation method and application of semi-sandwich iridium complex

A technology of iridium complexes and fluorescence characteristics, applied in the field of chemical pharmacy, can solve the problems of insufficient anti-cancer effect, low photostability, high cytotoxicity, etc., achieve excellent photophysical properties and photostability, large molar absorption coefficient, The effect of high anticancer activity

Active Publication Date: 2018-07-13
QUFU NORMAL UNIV
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  • Abstract
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  • Claims
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AI Technical Summary

Problems solved by technology

However, these small organic molecules have some disadvantages: poor water solubility, easy to produce precipitation in water environment (such as culture medium) or precipitate out immediately after interacting with cells, affecting the dyeing effect; relatively high cytotoxicity, dyes interact with cells After that, it leads to cell death, which affects the observation of the normal state of the cell; the photostability is low, due to the action of the active agent group (singlet oxygen, etc.) in the air or in the medium, the fluorescence of the dye is continuously weakened after the excitation wavelength is irradiated , the phenomenon of photodrifting is serious, which is not conducive to stable imaging; the intersection of excitation and emission spectra is serious (the stoke shift is small), generally around tens of nanometers, which is not conducive to distinguishing endogenous fluorescence and reducing the self-quenching of the dye itself
However, since the half-sandwich iridium complex itself has no fluorescent properties, the understanding of the anti-cancer effect of the half-sandwich iridium complex is not deep enough. poor selectivity among cancer cells

Method used

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  • Semi-sandwich iridium complex having fluorescent property and containing N-N two-tooth chelated ligand, and preparation method and application of semi-sandwich iridium complex
  • Semi-sandwich iridium complex having fluorescent property and containing N-N two-tooth chelated ligand, and preparation method and application of semi-sandwich iridium complex
  • Semi-sandwich iridium complex having fluorescent property and containing N-N two-tooth chelated ligand, and preparation method and application of semi-sandwich iridium complex

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Weigh 0.5g IrCl 3 ·nH 2 4 parts of O were added to 4 inner tanks of the microwave digestion apparatus respectively, 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 passed, and the lids of the tanks were closed , Assemble the main tank and the standard tank, set the parameters of the microwave digestion instrument, react with the microwave digestion instrument, filter the obtained product, and remove the unreacted IrCl 3 ·nH 2 0, the liquid is spin-dried, and the solid obtained is dissolved with dichloromethane together with the crystal in the inner tank, and ether is added, and the single crystal is cultivated by the diffusion method to obtain the orange-yellow iridium dimer (R in the formula (1) A 1 = methyl) product, yield 51.4%.

Embodiment 2

[0049] Weigh 0.5g IrCl 3 ·nH 2 4 parts of O were added to 4 inner tanks of the microwave digestion apparatus respectively, and 1.3g of 1-biphenyl, 2,3,4,5-tetramethylcyclopentadiene, 20mL of methanol were added to each tank, ultrasonically, and nitrogen , cover the tank lid, assemble the main tank and the standard tank, set the parameters of the microwave digestion instrument, react with the microwave digestion instrument, filter the obtained product, and remove the unreacted IrCl 3 ·nH 2 O, the liquid is spin-dried, and the obtained solid is dissolved with dichloromethane together with the crystals in the inner tank, and ether is added, and the single crystal is cultivated by the diffusion method to obtain the orange-yellow iridium dimer (R in formula (1) A 1 = biphenyl) product, yield 20.6%.

Embodiment 3

[0051] Synthesis of Ligand L: Take 0.098g of rhodamine B hydrazide and 0.05g of 5-formyl-o-phenanthroline in a 100ml round bottom flask, add 30ml of dichloromethane as a solvent, add a drop of formic acid, and heat to reflux at 45°C After 24 hours, the solution changed from rose red to red. TLC detected the reaction process, and new substances were produced. The spin-dried liquid was a red oil. After adding a small amount of methanol, it was placed in the refrigerator for a period of time. filter, the filter cake was washed several times with methanol, the filtrate was rose red, vacuum-dried, and the filter cake was taken to obtain an off-white powder product. Yield 53.6%.

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Abstract

The invention relates to a semi-sandwich iridium complex having fluorescent properties and containing N-N two-tooth chelated ligand and belongs to the field of chemical pharmaceutical. The molecular structural formula of the iridium complex is as shown in the specification. As the iridium complex is creatively modified with rhodamine B, the whole complex has high anti-cancer activity and mitochondria targeting, has selectivity upon cancer cells, action process visibility and ideal purposes of real-time detection, and has a great significance on medicine targeting research. N-N is adopted as anion ligand for two-tooth chelation, the novel anionic iridium complex with relatively high anti-cancer activity and fluorescent properties can be synthesized, and the complex is good in effect and high in activity in cancer prevention and cell imaging.

Description

technical field [0001] The invention relates to a metal complex, in particular to a semi-sandwich iridium complex containing N^N bidentate chelating ligands with fluorescence characteristics, belonging to the field of chemical pharmacy. Background technique [0002] Cancer is one of the major diseases that seriously endanger human health. Overcoming cancer has always been a research topic attracting worldwide attention. Many metal complexes have anti-tumor activity and induce tumor cell apoptosis. Therefore, the research on the types, structures, properties, mechanisms of action and application status of anti-cancer drugs is the research content of anti-cancer drugs inducing tumor cell apoptosis. Therefore, it is a current research hotspot to search for new metal anticancer drugs with different mechanisms of action to improve or supplement the performance of existing platinum-based drugs. In addition, with the increasing research on cells, biomedical optical imaging such as...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/02C09K11/06A61K31/555A61K49/00A61K47/54A61P35/00
Inventor 刘哲马文丽郭丽华田珍珍李娟娟张均铭
Owner QUFU NORMAL UNIV
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