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Phthalocyanine iridium complex, as well as preparation method and application thereof

A complex, iridium phthalocyanine technology, applied in pharmaceutical formulations, medical preparations containing active ingredients, drug combinations, etc., can solve problems such as damage, unfavorable biological diagnosis and treatment applications, and achieve simple reaction steps and convenient purification process. , The effect of high photothermal conversion efficiency

Inactive Publication Date: 2016-09-28
SHANGHAI NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is well known that ultraviolet light has a certain harmful effect on the human body, which is not conducive to the application of biological diagnosis and treatment. In order to expand the light source of photodynamic therapy of metal iridium complexes to visible light, researchers are developing a new generation of photosensitizers

Method used

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  • Phthalocyanine iridium complex, as well as preparation method and application thereof
  • Phthalocyanine iridium complex, as well as preparation method and application thereof
  • Phthalocyanine iridium complex, as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] (1) Preparation of iridium phthalocyanine complexes

[0039] Weigh 67.2 mg of [Ir(COD)Cl] 2 and 109 mg of butoxy substituted phthalocyanine were placed in a 50 mL three-necked flask, vacuumed and filled with nitrogen, and circulated three times. Inject 20mL of toluene, under the protection of nitrogen, react at 100°C for 12h;

[0040] (2) Purification of iridium phthalocyanine complexes

[0041] The reaction liquid after the reaction in step (1) is rotary evaporated to remove the solvent, add a small amount of silica gel to mix the sample, weigh 200-300 mesh silica gel 30-70 times the amount of sample loading, and use dichloromethane: acetone about 150: 1 eluent developed column chromatography. The collected liquid was spin-dried, rinsed with anhydrous ether, and dried at a temperature of 70°C-100°C to obtain a sample.

Embodiment 2

[0043] (1) Preparation of iridium phthalocyanine complexes

[0044] Weigh 80.4mg of [Ir(COD)Cl] 2 and 109 mg of butoxy substituted phthalocyanine were placed in a 50 mL three-necked flask, vacuumed and filled with nitrogen, and circulated three times. Inject 20mL of ethylene glycol, under nitrogen protection, react at 100°C for 16h;

[0045] (2) Purification of iridium phthalocyanine complexes

[0046] The reaction liquid after the reaction in step (1) is rotary evaporated to remove the solvent, add a small amount of silica gel to mix the sample, weigh 200-300 mesh silica gel 30-70 times the amount of sample loading, and use dichloromethane: acetone about 150: 1 eluent developed column chromatography. The collected liquid was spin-dried, rinsed with anhydrous ether, and dried at a temperature of 70°C-100°C to obtain a sample.

Embodiment 3

[0048] (1) Preparation of iridium phthalocyanine complexes

[0049] Weigh 80.4mg[Ir(COD)Cl] 2 and 109mg of Pc were placed in a 50mL three-necked flask, evacuated and filled with nitrogen, and circulated three times. Inject 20mL of toluene, under the protection of nitrogen, react at 100°C for 18h;

[0050] (2) Purification of iridium phthalocyanine complexes

[0051] The reaction liquid after the reaction in step (1) is rotary evaporated to remove the solvent, add a small amount of silica gel to mix the sample, weigh 200-300 mesh silica gel 30-70 times the amount of sample loading, and use dichloromethane: acetone about 150: 1 eluent developed column chromatography. The collected liquid was spin-dried, rinsed with anhydrous ether, and dried at a temperature of 70°C-100°C to obtain a sample.

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Abstract

The invention belongs to the field of near infrared photo-thermal conversion materials, and particularly relates to a phthalocyanine iridium complex with a near infrared photo-thermal conversion property, as well as a preparation method and application thereof. The method comprises the following steps: adding [Ir(COD)Cl]2 and phthalocyanine serving as raw materials into a solvent under protection of nitrogen, and reacting for 6-24 hours at 100-200 DEG C; performing spin steaming on the reaction liquid to remove the solvent, performing chromatographic separation with a silica gel column, performing revolving drying on the collected liquid, flushing and drying; or cooling and filtering the obtained reaction liquid, dissolving the filter cake with dichloromethane, filtering, performing revolving drying on the collected filtrate, flushing with anhydrous ether, and drying to obtain a sample. The phthalocyanine iridium complex has good absorbability at nearly 800nm, can be used for converting near infrared light into thermal energy, and has good thermal stability. Furthermore, temperature can be increased to 55 DEG C in 15 minutes under excitation of 808nm laser, cancer cells can be effectively killed, and the phthalocyanine iridium complex is an excellent photo-thermal conversion reagent in the technology of photo-thermal treatment.

Description

technical field [0001] The invention belongs to the field of near-infrared photothermal conversion materials, and in particular relates to a phthalocyanine iridium complex with near-infrared photothermal conversion properties and a preparation method and application thereof. Background technique [0002] Photothermal therapy technology is an important minimally invasive treatment technology. This technology uses photothermal conversion reagents to convert the light energy of laser light into heat energy, so as to achieve the purpose of killing cells at high temperature. Its characteristics include accurate positioning and killing of diseased cells or tissues. Among the many hyperthermia technologies, near-infrared hyperthermia has attracted more attention. At present, the near-infrared photothermal conversion reagents that have been studied are mainly divided into noble metal nanomaterials, such as gold, palladium and other nanomaterials with different shapes; carbon materia...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22A61K41/00A61P35/00
CPCA61K41/0052C07D487/22
Inventor 杨红王杰靳红玉杨琪邓晶晶秦冬冬崔丽丽杨仕平
Owner SHANGHAI NORMAL UNIVERSITY