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Iridium complex, preparation method thereof and photodynamic therapy drug

A technology of iridium complexes and compounds, applied in the field of biomedicine, can solve the problems of poor water solubility, long cell penetration time, low cell uptake rate, etc.

Inactive Publication Date: 2020-10-23
SHENZHEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of this application is to provide an iridium complex and its preparation method, as well as a photodynamic therapy drug, which aims to solve the problems of poor water solubility, low cell uptake rate and long cell penetration time of existing metal complex photosensitizers to a certain extent. The problem

Method used

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  • Iridium complex, preparation method thereof and photodynamic therapy drug
  • Iridium complex, preparation method thereof and photodynamic therapy drug
  • Iridium complex, preparation method thereof and photodynamic therapy drug

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preparation example Construction

[0061] The second aspect of the embodiment of the present application provides a method for preparing an iridium complex, comprising the following steps:

[0062] S10. Compound A is mixed with concentrated sulfuric acid and subjected to a sulfonation reaction to separate and obtain sulfonated compound B;

[0063] S20. Using the first basic salt to neutralize compound B to obtain compound C;

[0064] S30. Dissolving the compound C and the iridium precursor in the first organic solvent, performing a coordination reaction, and separating to obtain the first iridium complex;

[0065] Wherein, the structural general formula of compound A is:

[0066] or

[0067] When the structural formula of the compound A is A1, the structural formula of the first iridium complex is I-1; when the structural formula of the compound A is A2, the structural formula of the first iridium complex is II-1:

[0068]

[0069] Among them, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 are ...

Embodiment 1

[0138] A kind of methoxy-porphyrin-iridium complex, the synthetic route diagram is attached figure 1 As shown, the following preparation steps are included:

[0139] ①Take 4.00g TMPP (5,10,15,20-tetrakis-(4-methoxyphenyl)-porphyrin) and 40.0mL (98.0%H 2 SO 4 ) in a mortar and grind to a uniform paste. The paste was transferred to a 250 mL round bottom flask, then 60 mL of 98% H 2 SO 4 , and the mixture was stirred and heated in an oil bath at 105° C. for 6 h.

[0140]②Put the mixture in a 400mL beaker and let it stand at room temperature for 48 hours. Then slowly add 300 mL of deionized water and stir. After cooling, filter with a G5 sintered glass filter to remove unreacted TMPP in the solution, add 200 mL of acetone to the filtrate, and stir to precipitate out the precipitate. The resulting precipitate was washed twice with acetone. Acetone was removed, and the solid product was dissolved in 150 mL of deionized water and washed with saturated NaHCO 3 Neutralized to ...

Embodiment 2

[0144] A kind of triphenylphosphine-porphyrin-iridium complex, the synthetic route diagram is as attached figure 2 As shown, the following preparation steps are included:

[0145] ① Take TPP (tetraphenylporphyrin, 4.00g, 6.5mmol) and paraformaldehyde (0.1351g, 1.5mmol), appropriate amount of hydrochloric acid, anhydrous zinc chloride and acetone, mix them in a 150mL round-bottomed flask, 70 ℃, 3h. After the reaction was finished, it was washed with deionized water, and the organic phase was separated and retained. The organic phase was rotary evaporated to remove acetone, and the solid was separated and purified by column chromatography to obtain compound a.

[0146] ②Take a and 40.0mL (98.0%H 2 SO 4 ) in a mortar and grind to a uniform paste. The paste was transferred to a 250mL round bottom flask, and then 60mL of 98% H 2 SO 4 , and the mixture was stirred and heated in an oil bath at 90-120°C for 6h. Put the mixture in a 400mL beaker, cool to room temperature, then...

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Abstract

The invention belongs to the technical field of biological medicine, and particularly relates to an iridium complex, the structural general formula of the iridium complex is shown as a following formula I or formula II: wherein R1, R2, R3, R4, R5, R6, R7 and R8 are respectively and independently selected from one of hydrogen, alkoxy and aryl; Y1 and Y2 are ions counteracting the iridium complex main body; n1, n2, m1 and m2 are ionic valences, the absolute value of n1 is equal to the absolute value of n2, and the absolute value of m1 is equal to the absolute value of m2. The iridium complex disclosed by the invention is good in water solubility, can be specifically combined with cytolysosome, can generate singlet oxygen under an illumination condition, has an obvious photodynamic therapy effect on cells, does not generate singlet oxygen under a dark condition, does not have toxicity, and has a wide application prospect in photodynamic therapy drugs.

Description

technical field [0001] The application belongs to the technical field of biomedicine, and in particular relates to an iridium complex, a preparation method thereof, and a photodynamic therapy drug. Background technique [0002] Photodynamic therapy (Photodynamic therapy, PDT) is a relatively new noninvasive treatment method for tumors, which relies on specific wavelength light source irradiation to activate photosensitizers in tumor tissues to produce biologically toxic singlet oxygen and other reactive oxygen species (Reactive oxygen species, ROS ), and then oxidatively damage tumors, virus-infected cells and other hyperproliferative cells, activate anti-tumor and anti-viral immunity, damage blood vessels, kill bacteria, fungi, viruses, and eliminate inflammation. Medical scientists have found that the acid extract of mammalian blood can effectively inhibit the growth of tumors after being exposed to light, and the first generation of photosensitizer, hematoporphyrin, was p...

Claims

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Application Information

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IPC IPC(8): C07D487/22A61K41/00A61P35/00
CPCA61K41/0076A61P35/00C07D487/22
Inventor 张平玉陈海杰任奇志张黔玲
Owner SHENZHEN UNIV
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