A kind of dicyanoiridium complex and its preparation method and application

A technology of iridium complexes and complexes, which is applied in the direction of medical preparations containing active ingredients, pharmaceutical formulas, indium organic compounds, etc., can solve the problem of low ability and achieve the effect of simple synthesis steps

Active Publication Date: 2022-04-12
GANNAN NORMAL UNIV
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Problems solved by technology

However, photosensitizers currently used in photodynamic therapy produce 1 o 2 low ability

Method used

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  • A kind of dicyanoiridium complex and its preparation method and application
  • A kind of dicyanoiridium complex and its preparation method and application
  • A kind of dicyanoiridium complex and its preparation method and application

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preparation example Construction

[0035] The present invention provides the preparation method that contains dicyanoiridium complex described in above-mentioned technical scheme, comprises the following steps:

[0036] Mixing 2-chloroisoquinoline, benzothiophene-2-boronic acid, potassium carbonate, tetrakis(triphenylphosphine)palladium and the first solvent, and performing a coupling reaction to obtain a ligand of the structure shown in formula II;

[0037] Mixing the ligand with the structure shown in the formula II, iridium trichloride trihydrate and the second solvent, and performing the first coordination reaction to obtain the ligand with the structure shown in the formula III;

[0038] The ligand of the structure shown in the formula III, 4,4'-dicyano-2,2'-bipyridine and the third solvent are mixed to carry out the second coordination reaction, and the obtained iridium complex containing chloride ion Mix with potassium hexafluorophosphate, carry out ion exchange reaction, obtain the dicyanoiridium comple...

Embodiment 1

[0057] Bicyanoiridium complex [(btpq) 2 -Ir-bpy-2CN)][PF 6 ]Synthesis:

[0058] Weigh 163.6mg of 2-chloroisoquinoline, 195.8mg of benzothiophene-2-boronic acid, 414.6mg of potassium carbonate and 92.4mg of Pd(PPh 3 ) 4 Dissolve in a mixed solvent of 10mLTHF and 10mL water, stir and heat to 75°C for 24h under nitrogen protection; after the reaction, cool the obtained material to room temperature, and dilute the obtained mixture with CH 2 Cl 2 After 3 extractions, back-extracted with water, the organic phase was collected, dried over anhydrous sodium sulfate and evaporated to dryness, the obtained crude product was distilled with CH 2 Cl 2 / petroleum ether (1:1, v / v) is purified as eluent, obtains the ligand (btpq) of structure shown in formula II;

[0059] Add 182.9 mg of the ligand represented by the formula II and 105.8 mg of iridium trichloride trihydrate into 30 mL of ethylene glycol ether and 10 mL of water mixed solvent, and reflux the resulting mixture at 110° C. f...

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Abstract

The invention provides a complex containing dicyanoiridium and its preparation method and application, belonging to the technical field of photosensitizers. The invention is based on the fact that the central iridium atom of the metal iridium complex is a heavy atom, and the long-lived triplet excited state of the metal iridium complex is regulated by introducing a dicyano group structure into the N^N ligand, which is conducive to inducing the generation of active oxygen species (such as singlet oxygen and hydroxyl radicals), increasing the ability of metal iridium complexes to produce active oxygen; under light conditions, the complex containing dicyanoiridium can produce singlet oxygen and Reactive oxygen species such as hydroxyl radicals, and the ability to photodynamically kill tumor cells, provide the possibility to construct dicyano-containing iridium complexes for photodynamic therapy.

Description

technical field [0001] The invention relates to the technical field of photodynamic therapy, in particular to a complex containing dicyanoiridium and its preparation method and application. Background technique [0002] Metallic iridium complexes rely on metal centers and ligands to be excited, and the strong spin-orbit coupling in iridium complexes leads to singlet and triplet mixing, which leads to excellent photophysical properties, including good photostability , high quantum yield, large Stokes shift and long lifetime. In recent years, metal iridium complexes have a long-lived triplet excited state because the central iridium atom is a heavy atom, which is conducive to its full contact with oxygen to generate 1 o 2 , the potential application value of the photodynamic effect of iridium complexes in the field of photodynamic therapy has attracted widespread attention. [0003] Photosensitizers with the ability to generate singlet oxygen and hydroxyl radical active oxy...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00A61K41/00A61P35/00
CPCC07F15/0033A61K41/0057A61P35/00
Inventor 吴勇权吴洁郭维李亿保范小林
Owner GANNAN NORMAL UNIV
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