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A kind of iridium complex containing phenothiazine and its preparation method and application

A technology of phenothiazine iridium and iridium complexes, which is applied in the field of phenothiazine iridium complexes and their preparation, can solve the problems of low efficiency and achieve strong tissue penetration, low background autofluorescence, and small photodamage Effect

Active Publication Date: 2022-04-12
GANNAN NORMAL UNIV
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, photosensitizers for photodynamic therapy produce 1 o 2 less efficient

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  • A kind of iridium complex containing phenothiazine and its preparation method and application
  • A kind of iridium complex containing phenothiazine and its preparation method and application
  • A kind of iridium complex containing phenothiazine and its preparation method and application

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preparation example Construction

[0042] The present invention provides the preparation method of the iridium complex containing phenothiazine described in the above technical scheme, comprising the following steps:

[0043] Mixing phenothiazine, 4-bromobenzonitrile, palladium acetate, tri-tert-butylphosphine, cesium carbonate and the first solvent, and performing a carbon-nitrogen coupling reaction to obtain a compound of the structure shown in formula II;

[0044] Mixing the compound with the structure shown in the formula II, 4-methyl-2,2'-bipyridine-4-carbaldehyde, a base and a second solvent, and performing a condensation reaction to obtain the ligand with the structure shown in the formula III;

[0045] Mix 2-chloroisoquinoline, benzothiophene-2-boronic acid, potassium carbonate, tetrakis(triphenylphosphine)palladium and a third solvent, and carry out a coupling reaction to obtain a ligand of the structure shown in IV;

[0046] Mixing the ligand with the structure shown in the formula IV, iridium trichlo...

Embodiment 1

[0073] Iridium complexes containing phenothiazine [Ir(btpq) 2 (PTZ-MN-bpy)][PF 6 ]Synthesis:

[0074] Weigh 300.0mg of phenothiazine, 292.6mg of 4-bromobenzonitrile, 90.2mg of palladium acetate, 910.8mg of tri-tert-butylphosphine and 651.8mg of cesium carbonate, dissolve in 150mL of toluene, and reflux at 110°C for 24h in a nitrogen atmosphere After the reaction finishes, the gained material is extracted with dichloromethane, and the gained aqueous phase is extracted three times with dichloromethane, and the combined organic phases are dried overnight with anhydrous sodium sulfate, separated by column chromatography (reagent is dichloromethane:petroleum ether) =10:1 (v / v), obtain the ligand of structure shown in formula II (recorded as PTZ-MN);

[0075] Weigh 494.3mg of the ligand (PTZ-MN) and 198.1mg of 4-methyl-2,2'-bipyridine-4-carbaldehyde and 120mg of sodium hydroxide, dissolved in 100mL of ethanol, at room temperature After the reaction, the obtained material was cool...

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Abstract

The invention provides a phenothiazine-containing iridium complex, a preparation method and application thereof, and belongs to the technical field of photosensitizers. The present 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 phenothiazine, and the emission spectrum of the designed iridium complex containing a phenothiazine structure is located near In the infrared region, it belongs to the iridium complex that emits near-infrared phosphorescence; the present invention introduces a phenothiazine structure into the N^N ligand of the iridium complex, which can increase the generation of the iridium complex 1 o 2 Ability. The iridium complex provided by the invention can generate singlet oxygen in both the solution and tumor cells under the illumination condition of >470nm, and has the ability of photodynamically killing cancer cells, which provides the possibility for photodynamic therapy.

Description

technical field [0001] The invention relates to the technical field of photodynamic therapy, in particular to a phenothiazine-containing iridium complex and a preparation method and application thereof. Background technique [0002] Metal phosphorescent iridium complexes rely on metal centers and ligands to make them excited, strong spin-orbit coupling in iridium complexes leads to singlet triplet mixing, which leads to excellent photophysical properties, including good photostability properties, high quantum yield, large Stokes shift, and long phosphorescence lifetime. Since the iridium (III) complex has a triplet excited state, energy transfer occurs between the triplet excited state and the surrounding molecular oxygen, which can induce the generation of singlet oxygen in the cytotoxic reactive oxygen species. Therefore, iridium complexes can be used as photosensitizers for photodynamic therapy to directly or indirectly kill cancer cells under light irradiation. [0003...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C09K11/06A61K41/00A61P35/00
CPCC07F15/0033C09K11/06A61K41/0057A61P35/00C09K2211/185
Inventor 吴勇权吴洁李媛艳李勋范小林
Owner GANNAN NORMAL UNIV
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