Porene-iridium metal complex and its preparation method and application

A technology of iridium metal complexes and porphynes, applied in the field of metal complex synthesis, can solve problems such as low absorption intensity, slow removal, complex structure, etc., and achieve triplet efficiency increase, absorption intensity enhancement, and good application prospects. Effect

Inactive Publication Date: 2018-04-13
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although they are all effective photosensitizers, there are still some shortcomings in this class of photosensitizers: (1) the complex structure is difficult to synthesize and separate; (2) the absorption intensity is very low in the transparent window range (650-900nm) of biological tissues , the penetration of light in the tissue is not high enough; (3) the elimination from the body is slow, and there is a long-lasting photosensitivity damage to the skin
However, there is no relevant record about porene-iridium metal complexes

Method used

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  • Porene-iridium metal complex and its preparation method and application
  • Porene-iridium metal complex and its preparation method and application
  • Porene-iridium metal complex and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Synthesis of Octaethylporene Ligand

[0022]

[0023] Mix zinc powder (1.161g, 17.8mmol) and cuprous chloride (71mg, 0.72mmol) in a 500mL round bottom flask, add 35mL of dry THF under the protection of an inert gas, stir evenly, and maintain it for a period of time in an ice-water bath , to stabilize the temperature at around 0°C, slowly add TiCl dropwise 4 Solution (0.973 mL, 8.86 mmol) was added over 1 hour. Immediately thereafter the reaction mixture was heated to reflux for 2 h. After cooling to room temperature, the compound 2,2'-dipyrrole dialdehyde was dissolved in 200 mL of tetrahydrofuran, and slowly added to the reaction system with a syringe, and the addition was completed within 1 hour. Continue heating the mixture to reflux for 1 hour. After the reaction was completed, the system was immediately cooled to 0°C with an ice-water bath, and the prepared ammonia solution (70mL) with a mass concentration of 6% was dropped within 30 minutes. The color of the...

Embodiment 2

[0025] Preparation of Octaethylporene Iridium Chloride

[0026]

[0027] The porene compound (20mg, 3.74×10 -5 mol), a small amount of anhydrous sodium acetate and [Ir(COD) 2 Cl] 2 (30mg, 3.36×10 -5 mol) were mixed and dissolved in 10 mL of toluene solvent, reacted in the dark under the protection of an inert gas, and heated to reflux for 12 h. Cool naturally to room temperature, evaporate the solvent under reduced pressure, dissolve the crude product in a small amount of chloroform, wash with water and saturated brine for several times, dry the organic phase with anhydrous sodium sulfate, and evaporate the solvent to obtain the crude product. The obtained crude product was subjected to column separation, and dichloromethane was used as a developing solvent to collect blue-purple components, which were spin-dried and recrystallized (dichloromethane: n-hexane) to obtain 15 mg of the target compound as a purple solid, with a yield of 51%. 1 H NMR (CDCl 3 ,500MHz) δ:9.94(...

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Abstract

The invention discloses a porphyrin- iridium metal complex and a preparation method and application thereof and belongs to the technical field of synthesis of metal complexes. The porphyrin- iridium metal complex is of the structure as shown in the description, wherein R1 is hydrogen or alkyl or phenyl, R2 is hydrogen or alkyl or phenyl, and R3 is hydrogen or alkyl or phenyl. The invention further discloses the preparation method of the porphyrin- iridium metal complex and application of the porphyrin- iridium metal complex to preparation of photosensitizer in the field of photodynamics therapy. According to the porphyrin- iridium metal complex and the preparation method and application thereof, due to introduction of transition metal heavy atoms, triplet state efficiency of an obtained compound is increased, and furthermore efficiency of the compound for generating singlet oxygen is improved; meanwhile, a small number of steps are included in the reaction, and molecule design can be achieved easily by adjusting substituent groups on pyrrole.

Description

technical field [0001] The invention belongs to the technical field of synthesis of metal complexes, and in particular relates to a porene-iridium metal complex and its preparation method and application. Background technique [0002] Cancer is currently one of the deadliest physical diseases in the world, and billions of dollars are spent on research on how to treat cancer and improve cancer treatment every year. Using traditional surgery, radiotherapy, chemotherapy and other means to treat cancer often causes many side effects and affects the normal functions of various organs of the human body. [0003] Photodynamic therapy (PDT), as a minimally invasive means and method for treating various cancers with better controllability, has attracted more and more people's attention. Compared with other cancer treatment methods, photodynamic therapy has the following advantages: 1. It can treat cancer types that cannot be performed by surgery; For patients, photodynamic therapy ...

Claims

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Application Information

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Patent Type & AuthorityPatents(China)
IPC IPC(8): C07D487/22A61K41/00A61P35/00
CPCA61K41/0076C07D487/22
Inventor常毅沈珍李志勇
OwnerHENAN NORMAL UNIV