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Iridium complex photosensitizer as well as preparation method and application thereof

A technology of iridium complexes and photosensitizers, applied in the field of iridium complex photosensitizers and their preparation, can solve the problems of affecting the treatment effect of PDT, ROS short life, limited diffusion distance, etc., achieve high yield, improve effect, and preparation method simple effect

Pending Publication Date: 2022-07-29
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The ROS generated during PDT has a short lifetime (0.03-0.18 ms in a living system) and a limited diffusion distance (0.01-0.02 μm in a living system). Therefore, the primary position of ROS generation will directly affect the therapeutic effect of PDT
Therefore, if the photosensitizers are precisely delivered to important or fragile organelles, the aggregated photosensitizers can attack the "killer sites" of these cancer cells, causing more damage to the tumor tissue

Method used

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  • Iridium complex photosensitizer as well as preparation method and application thereof
  • Iridium complex photosensitizer as well as preparation method and application thereof
  • Iridium complex photosensitizer as well as preparation method and application thereof

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preparation example Construction

[0048] The invention provides the preparation method of the above-mentioned iridium complex photosensitizer, comprising the following steps:

[0049]S1, 1,10-phenanthroline-5,6-dione, terephthalaldehyde, ammonium acetate and acetic acid are reacted, and the pH of the mixture obtained by the reaction solution and water is adjusted to neutrality to obtain a mixture, and the mixture is sequentially Separate, dissolve, filter, and dry to obtain the ligand fmp;

[0050] S2. Under protective gas, react 2,3,3-trimethylindole, 1,3-propane sultone and o-dichlorobenzene to obtain compound 1;

[0051] S3, under protective gas, react the ligand fmp, compound 1, catalyst and mixed solvent 1, and mix the reaction solution with saturated sodium chloride solution and then separate and dry in sequence to obtain ligand psi;

[0052] S4, the IrCl 3 ·3H 2 O, 2-phenylpyridine and mixed solvent 2 react to obtain compound 2;

[0053] S5, under protective gas, react compound 2, ligand psi and mix...

Embodiment 1

[0082] 1,10-Phenanthroline-5,6-dione (2 mmol), terephthalaldehyde (4 mmol) and ammonium acetate (60 mmol) were dissolved in acetic acid (60 mL) and refluxed at 115 °C for 30 min. After cooling to room temperature, 250 mL of distilled water was added, and the pH was adjusted to neutrality with concentrated ammonia water (25% by mass) under stirring conditions, and a yellow solid was precipitated. Then carry out suction filtration, the crude product after suction filtration is washed three times with water, and the orange crude product obtained after drying at 80°C for 24 hours is then heated and dissolved in ethanol for 30min at 85°C, wherein the mass-volume ratio of the orange crude product to ethanol is 100mg: 200mL, after hot filtration, put the filtrate into a rotary dryer to spin dry to obtain the yellow ligand fmp with a yield of 70.0%;

[0083] Dissolve 2,3,3-trimethylindole (3.14 mmol) and 1,3-propane sultone (3.48 mmol) in 3 mL of o-dichlorobenzene, reflux at 120 °C fo...

Embodiment 2

[0088] IrCl 3 ·3H 2 O (2 mmol) and 2-phenylpyridine (4.4 mmol) were dissolved in 50 mL of mixed solvent (the volume ratio of ethylene glycol ether and water was 3:1), refluxed at 130 ° C for 24 h, cooled to room temperature, and then pumped After filtration, the crude product after suction filtration was dried at 80 °C for 24 h to obtain yellow compound 2 (Ir 2 (ppy) 4 Cl 2 ), the yield is 80%;

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Abstract

The invention belongs to the technical field of photodynamic therapy, and discloses an iridium complex photosensitizer as well as a preparation method and application thereof. The preparation method comprises the following steps: firstly, preparing a ligand fmp, a compound 1 and a compound 2; preparing a ligand psi by using fmp and a compound 1; and finally, preparing the iridium complex photosensitizer by using the ligand psi and a compound 2. The preparation process is simple, the reaction conditions are mild, the yield is high, and large-scale production conditions are provided. The prepared iridium complex photosensitizer is composed of a ring metal ligand, a metal center and an auxiliary ligand containing an N-substituted indole sulfonate structure, the luminous intensity of the iridium complex photosensitizer is enhanced along with the increase of illumination time, and the progress of photodynamic therapy can be monitored.

Description

technical field [0001] The invention relates to the technical field of photodynamic therapy, in particular to an iridium complex photosensitizer and a preparation method and application thereof. Background technique [0002] Photodynamic therapy (PDT) has received extensive attention due to its noninvasive, spatiotemporally controllable treatment modality. During photodynamic therapy, photosensitizers (PSs) have negligible cytotoxicity under dark conditions, but generate large amounts of reactive oxygen species (ROS) under light conditions, resulting in high cytotoxicity. The mechanism of ROS generation can generally be divided into two pathways: type I and type II. The type I pathway involves the transfer of electrons from the photosensitizer in the excited state to the surrounding substrate to form free radicals, such as O 2 ·- and OH·; while in the type II pathway, the photosensitizer in the excited state transfers energy to triplet oxygen molecules to form singlet oxy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06A61K41/00A61P35/00
CPCC07F15/0033C09K11/06A61K41/0057A61P35/00C09K2211/185C07B2200/07
Inventor 唐晓亮黄姗姗寇满昌邱锦琳窦伟刘伟生
Owner LANZHOU UNIVERSITY
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