Axially substitutive silicon phthalocyanine complex and doxorubicin conjugate thereof

A silicon phthalocyanine complex technology, applied in the field of axially substituted silicon phthalocyanine complexes and doxorubicin conjugates, can solve the problems of high skin phototoxicity, clinical application limitations, and unstable composition of the mixture. Achieve the effect of high cancer cell uptake rate and excellent amphiphilicity

Active Publication Date: 2016-06-15
FUZHOU UNIVERSITY
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  • Description
  • Claims
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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

Method used

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Examples

Experimental program
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Example Embodiment

[0039] The preparation method of the axial end dipeptide substituted silicon phthalocyanine of formula (2.1-2.2) includes the following steps:

[0040] 1) Using axial terminal carboxyl substituted silicon phthalocyanine and N-hydroxysuccinimide as reactants, using N,N-dimethylformamide as solvent, in 1-ethyl-(3-dimethylaminopropyl) In the presence of carbodiimide hydrochloride and under the protection of nitrogen, the reaction is stirred at -5~5°C for 1~2 hours, and then the reaction is stirred at room temperature~35°C for 12~36 hours, and then separated by column chromatography. The silicon phthalocyanine carboxyl activator is obtained; wherein the molar ratio of the axial terminal carboxyl substituted silicon phthalocyanine to the N-hydroxysuccinimide is 1:1.5~5, and the axial terminal carboxyl substituted silicon phthalocyanine is the axial end Carboxyl disubstituted silicon phthalocyanine Or axial asymmetric monocarboxyl substituted silicon phthalocyanine ; The amount of 1-...

Example Embodiment

[0053] Example 1

[0054] 2-[4-(2-aminoethyl)phenoxy]silicon phthalocyanine Synthesis

[0055] According to the published patent method (ZL201210155097.4), the specific steps are as follows:

[0056] Under the protection of nitrogen, add dichlorophthalocyanine silicon (244.7mg, 0.4mmol), 4-(2-aminoethyl)phenol 1.2~2mmol (preferably 1.6mmol) and NaH into 20~50mL toluene or xylene or two In oxane (preferably toluene, 30mL), reflux for 12~24 hours (preferably 18 hours); vacuum rotary evaporation to remove the solvent, use 100mL of dichloromethane to dissolve, centrifuge to remove insolubles, and extract the dichloromethane solution with water (3×100mL) ), collect the organic layer, then extract with dilute hydrochloric acid (0.1~0.5mmol), collect the water layer; neutralize the water layer with 1M sodium hydroxide, 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 DMS...

Example Embodiment

[0057] Example 2

[0058] Axially asymmetric monocarboxyl substituted silicon phthalocyanine Synthesis

[0059] According to the published application patent (ZL201410108985.X) for synthesis, the specific steps are as follows:

[0060] Under the protection of nitrogen, add dichlorosilicon phthalocyanine (100mg, 0.164mmol), p-hydroxyphenylpropionic acid (1.640~3.280mmol, preferably 4.920mmol) and NaH (0.01~0.02mmol, preferably 0.016mmol) to 7~15mL In toluene (preferably 10 mL), reflux for 12 to 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 insolubles, and then purified by silica gel column using ethyl acetate: tetrahydrofuran (1:1, v / v) as eluent The second component 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 683n...

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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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IPC IPC(8): C07F7/02C07D487/22C07K5/062A61K31/704A61K47/48A61K41/00A61P35/00
CPCA61K41/0071C07D487/22C07F7/025C07K5/06026
Inventor 黄剑东柯美荣陈少芳
Owner FUZHOU UNIVERSITY
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