Phenothiazine-containing iridium complex as well as preparation method and application thereof

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, small light damage, and low background autofluorescence Effect

Active Publication Date: 2021-08-20
GANNAN NORMAL UNIV
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Problems solved by technology

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

Method used

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  • Phenothiazine-containing iridium complex as well as preparation method and application thereof
  • Phenothiazine-containing iridium complex as well as preparation method and application thereof
  • Phenothiazine-containing iridium complex as well as preparation method and application thereof

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preparation example Construction

[0042] The present invention provides the above technical solution containing phenothiazine method for preparing an iridium complex, comprising the steps of:

[0043] Phenothiazine, 4-bromobenzonitrile, palladium acetate, tri-t-butylphosphine, cesium carbonate and the solvent are mixed first, carbonitriding coupling reaction, to give a compound of the structure shown in formula II;

[0044] The compound represented by the structure of formula II, 4- carbaldehyde methyl-bipyridine-2,2'-base and the second solvent are mixed -4-, condensation reaction, to obtain the ligand represented by structural formula III;

[0045] 2-chloro-isoquinoline, benzothiophene-2-boronic acid, potassium tetrakis (triphenylphosphine) palladium and the third solvent are mixed, the coupling reaction, to obtain the ligand structure shown in IV;

[0046] The ligand structure shown by the formula IV, iridium trichloride trihydrate and fourth mixed solvent, a first ligand, to give the structure of iridium compl...

Embodiment 1

[0073] Phenothiazine ruthenium complex [IR (btpq) 2 (PTZ-MN-BPY)] [PF 6 ]Synthesis:

[0074] 300.0 mg of phenothiazine, 292.6 mg of 4-bromine, 90.2 mg of acetate and 910.8 mg of tri-butylphosphine and 651.8 mg of cesium carbonate were dissolved in 150 ml of toluene, 110 ° C in a nitrogen protection atmosphere 24h After the reaction, the resulting material was extracted with dichloromethane to extract the resulting aqueous phase for dichloromethane, combined with an organic phase, dried over the air with anhydrous sodium sulfate, and the column chromatography was separated (the reagent was dichloromethane: petroleum ether) = 10: 1 (v / v), resulting in a ligand of the structure shown in Formula II (PTZ-Mn);

[0075] The ligand (PTZ-Mn) and 198.1 mg of 4-methyl-2,2'-bisin-4-formaldehyde shown in 494.3 mg of formula II were weighed, and sodium hydroxide was dissolved in 100 ml of ethanol, at room temperature. After the reaction was 3 h; After the reaction was completed, the resulting...

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Abstract

The invention provides a phenothiazine-containing iridium complex as well as a preparation method and application thereof, and belongs to the technical field of photosensitizers. On the basis that a central iridium atom of the metal iridium complex is a heavy atom, the long-life triplet excitation state of the metal iridium complex is regulated and controlled through phenothiazine, the emission spectrum of the designed iridium complex containing the phenothiazine structure is located in a near-infrared region, and the iridium complex belongs to near-infrared phosphorescence emission iridium complexes. The phenothiazine structure is introduced into the N^N ligand of the iridium complex, so that the capability of generating <1>O2 by the iridium complex can be improved. The iridium complex provided by the invention can generate singlet oxygen in both a solution and tumor cells under the illumination condition of more than 470nm, has the capability of photodynamically killing cancer cells, and provides possibility for photodynamic therapy.

Description

Technical field [0001] The present invention relates to the field of photodynamic therapy, particularly to a phenothiazine-containing iridium complex and its preparation method and application. Background technique [0002] Phosphorescent iridium metal complex depends on the ligands and the metal center so that it is excited, iridium complexes led to strong spin-orbit coupling of the tri-state mixing singlet, which makes it has excellent photophysical properties, including good light stability , high quantum yield, a large Stokes shift and a long phosphorescence life. Since iridium (III) complexes have a triplet excited state, the triplet excited state energy transfer occurs with molecular oxygen in the surrounding, can induce cytotoxic activity of singlet oxygen is oxygen. Therefore, the iridium complex can be used as photosensitizers in photodynamic therapy, directly or indirectly kills cancer cells under light irradiation. [0003] In recent years, due to the central iridium c...

Claims

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Application Information

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Patent Type & Authority Applications(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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