A kind of axially substituted phthalocyanine silicon complex and its doxorubicin conjugate

A technology of silicon phthalocyanine and complexes, applied in the field of axially substituted silicon phthalocyanine complexes and their doxorubicin conjugates, can solve the problem of high skin phototoxicity, limited clinical application, lack of efficient combination drugs, etc. problem, to achieve the effect of high cancer cell uptake rate and excellent amphiphilicity

Active Publication Date: 2018-01-12
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although hematoporphyrin derivatives have shown certain curative effects, they have also exposed their serious shortcomings: the maximum absorption wavelength (380-420nm) is not in the red light region (650-800nm) with better transmittance to human tissue, skin phototoxicity Large, and the composition of the mixture is unstable, which limits its clinical application
However, there is still a lack of highly effective combination drugs, especially those with targeted functions

Method used

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Examples

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preparation example Construction

[0041] The preparation method of the axial terminal dipeptide substituted silicon phthalocyanine described in the formula (2.1-2.2) comprises the following steps:

[0042] 1) With the axial terminal carboxyl substituted silicon phthalocyanine and N-hydroxysuccinimide as reactants, N,N-dimethylformamide as solvent, in 1-ethyl-(3-dimethylaminopropyl In the presence of carbodiimide hydrochloride and under the protection of nitrogen, stir and react at -5~5°C for 1~2 hours, then continue to stir and react at room temperature~35°C for 12~36 hours, and then use column chromatography to separate Obtain silicon phthalocyanine carboxyl activator; Wherein, the molar ratio of axial terminal carboxyl substituted silicon phthalocyanine and N-hydroxysuccinimide is 1:1.5~5, described axial terminal carboxyl substituted silicon phthalocyanine is the axial terminal Carboxyl disubstituted silicon phthalocyanine Or axial asymmetric monocarboxy substituted silicon phthalocyanine ; The amount o...

Embodiment 1

[0056] 2-[4-(2-Aminoethyl)phenoxy]silicone phthalocyanine Synthesis

[0057] According to the published patent method (ZL201210155097.4), the specific steps are as follows:

[0058] Under nitrogen protection, dichlorophthalocyanine silicon (244.7mg, 0.4mmol), 4-(2-aminoethyl)phenol 1.2~2mmol (preferably 1.6mmol) and NaH were added to 20~50mL toluene or xylene or di Oxycycline (preferably toluene, 30mL), reflux for 12~24 hours (preferably 18 hours); vacuum rotary evaporation to remove solvent, use 100mL dichloromethane to dissolve, centrifuge to remove insoluble matter, dichloromethane solution is extracted with water (3×100mL ), collect the organic layer, then extract with dilute hydrochloric acid (0.1-0.5 mmol), and collect the aqueous layer; neutralize the aqueous layer with 1M sodium hydroxide, and precipitate a blue precipitate, centrifuge, wash with water, and dry in vacuo to obtain a blue product. The rate is 45%. The maximum absorption peak of the product in DMSO is...

Embodiment 2

[0060] Axially asymmetric monocarboxy substituted silicon phthalocyanine Synthesis

[0061] According to the published patent application (ZL 201410108985.X), the specific steps are as follows:

[0062] Under the protection of nitrogen, dichlorosilicon phthalocyanine (100 mg, 0.164 mmol), p-hydroxyphenylpropionic acid (1.640~3.280 mmol, preferably 4.920 mmol) and NaH (0.01~0.02 mmol, preferably 0.016 mmol) were added to 7~ In 15 mL of toluene (preferably 10 mL), reflux for 12-24 hours (preferably 12 hours). The solvent was removed by vacuum rotary evaporation, and washed with water to obtain a blue crude product; the crude product was dissolved in tetrahydrofuran, filtered to remove insoluble matter, and then purified by silica gel column, using ethyl acetate: tetrahydrofuran (1:1, v / v) as eluent The second fraction was collected, concentrated and dried to obtain a blue product with a yield of 35.00%. The maximum absorption peak of the product in DMF is located at 683 nm, ...

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Abstract

The invention discloses an axially substitutive silicon phthalocyanine complex and a doxorubicin conjugate thereof and a preparation method and application of the axially substitutive silicon phthalocyanine complex and the doxorubicin conjugate thereof, and belongs to the technical field of photosensitizer and drug preparation.The complex can be prepared into a novel efficient photodynamic drug or photosensitizer, and the complex and doxorubicin can be prepared into the silicon phthalocyanine-doxorubicin conjugate.The coupling agent has both a photodynamic therapy effect and a chemotherapy effect and can be prepared into a novel anti-cancer drug.

Description

technical field [0001] The invention belongs to the technical field of medicine preparation, and specifically relates to an axially substituted phthalocyanine silicon complex and a doxorubicin conjugate, as well as their preparation method and application. Background technique [0002] Photodynamic therapy (or photodynamic therapy) is essentially the application of the photosensitization reaction of photosensitizers (or photosensitizers) in the medical field. After the target is relatively enriched, the target is irradiated with light of a specific wavelength (for the target in the body cavity, the light source can be introduced with the help of interventional technology such as optical fiber), so that the photosensitizer enriched in the target undergoes a series of light excitation under light excitation. Physical and photochemical reactions generate reactive oxygen species, which then destroy the target body (such as cancer cells and cancer tissues). Therefore, the key to ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/02C07D487/22C07K5/062A61K31/704A61K47/54A61K47/64A61K41/00A61P35/00
CPCA61K41/0071C07D487/22C07F7/025C07K5/06026
Inventor 黄剑东柯美荣陈少芳
Owner FUZHOU UNIV
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