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Application of piperazidine substituted silicon phthalocyanine and application thereof to photothermal therapy

A technology of photothermal therapy and silicon phthalocyanine, which is applied in the field of photothermal agents and photothermal therapy drugs, can solve the problems that have not yet been seen in the application research of phthalocyanine photothermal therapy, and achieve good industrialization prospects, stable properties, and tissue penetration powerful effect

Active Publication Date: 2018-03-13
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in terms of cancer treatment, the research on phthalocyanine is currently limited to photodynamic therapy (PDT), and there is no application research on phthalocyanine as photothermal therapy.

Method used

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  • Application of piperazidine substituted silicon phthalocyanine and application thereof to photothermal therapy
  • Application of piperazidine substituted silicon phthalocyanine and application thereof to photothermal therapy
  • Application of piperazidine substituted silicon phthalocyanine and application thereof to photothermal therapy

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Synthesis of silicon phthalocyanine with the following structure

[0036] in:

[0037]The compound can be named: bis[4-(4-acetylpiperazine)]silicon phthalocyanine, and the target product was prepared with reference to the inventor's paper published in Bioorg.Med.Chem.Lett., 2006, 16, 2450-2453: Disperse dichlorosilicon phthalocyanine and 1-acetyl-4-(4-hydroxyphenyl)piperazine at a molar ratio of 1:8 to 11 in anhydrous toluene, and reflux for 48 hours in the presence of NaH. After the reaction was complete, the toluene was evaporated to dryness, rinsed with a large amount of water, and dried in vacuum. The crude product was separated and activated by silica gel chromatography, and the eluent was acetone. The yield was 62%. The characterization data of the product are as follows:

[0038] 1 HNMR (CDCl 3 ,400MHz,ppm): δ9.59-9.62(m,8H,Pc-H α ),8.34-8.36(m,8H,Pc-H β ), 5.18 (d, J=8.1Hz, 4H, Ph-H β ),3.35-3.36(m,4H,CH 2 ),3.17-3.18(m,4H,CH 2 ), 2.38 (d, J=8.1Hz...

Embodiment 2

[0042] Synthesis of silicon phthalocyanine with the following structure

[0043] in:

[0044] The compound can be named as: bis[4-(1-methyl-4-acetylpiperazine)] silicon phthalocyanine diiodide. Prepare the target product with reference to the papers published by the inventor in Bioorg.Med.Chem.Lett., 2006, 16, 2450-2453: dissolving bis[4-(4-acetylpiperazine)] silicon phthalocyanine in chloroform , made into a saturated solution, adding excess methyl iodide, refluxed for 1 hour, cooled to room temperature and stirred for 12 hours, a large amount of insoluble matter was precipitated, filtered to obtain the corresponding target product with a yield of 87%.

[0045] The characterization data of the product are as follows:

[0046] 1 HNMR (CDCl 3 , 400MHz, ppm) data and its attribution: δ9.64-9.67 (m, 8H, Pc-H α ),8.50-8.53(m,8H,Pc-H β ), 6.25 (d, J=9.3Hz, 4H, Ph-H β ),3.27-3.29(m,8H,CH 2 ), 2.59 (d, J=9.3Hz, 4H, Ph-H α ),2.56(s,6H,N-CH 3 ),2.48-2.50(m,8H,CH 2 ),2.17...

Embodiment 3

[0051] Synthesis of silicon phthalocyanine with the following structure

[0052] in:

[0053] This compound can be named as: two [4-(1-piperazinyl) phenoxy] silicon phthalocyanine, preparation method is as follows:

[0054] Using dichlorosilicon phthalocyanine and 4-(1-piperazinyl)phenol or 3-(N-piperidine)propionic acid as reactants, the molar ratio of the two is 1:1~20 (optimum 1:3 ), with toluene, xylene or dioxane as a solvent, with NaH as a catalyst, under the protection of nitrogen, react for 1 to 36 hours (optimum 24 hours) at 100 to 130 ° C, and the solvent consumption is every 0.1mmol two Chlorosilicon phthalocyanine needs 6-10mL, and the amount of NaH is 0.3-0.5mmol per 0.1mmol of dichlorosilicon phthalocyanine. After the reaction was complete, the toluene was evaporated to dryness, washed with a large amount of water, and dried under vacuum to obtain a blue crude product. The crude product is separated by silica gel chromatography, the eluent is ethyl acetate...

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Abstract

The invention discloses application of piperazidine substituted silicon phthalocyanine and application thereof to photothermal therapy, and belongs to the field of a photothermal agent or photothermaltherapy medicine. A solution containing the silicon phthalocyanine provided by the invention has the obvious photoinduced temperature rising effect under the illumination of near infrared laser; thephotothermal therapy can be realized; meanwhile, the photodynamic active oxygen generation effect is also achieved; the cooperated effect of photodynamic therapy and photodynamic therapy can be achieved.

Description

technical field [0001] The invention belongs to the field of photothermal agents and photothermal therapeutic drugs, and in particular relates to silicon phthalocyanines containing piperazine groups and analogues thereof in the axial direction, as well as their preparation methods and applications. Background technique [0002] With the development of science and technology, new tumor treatment methods continue to emerge. Among them, photodynamic therapy (PDT) and photothermal therapy (PTT) have attracted extensive attention and research due to their high selectivity to tumor tissue, small trauma, and low toxicity and side effects. [0003] PDT kills cancer cells by using photosensitizers to generate reactive oxygen species (Reactive oxygen species, ROS) under light. According to the type of ROS and the way of production, PDT can be divided into two mechanisms: type I and type II. In the type I mechanism, the excited-state photosensitizer directly undergoes electron transf...

Claims

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Application Information

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IPC IPC(8): A61K41/00A61P35/00C07F7/10
CPCA61K41/0052A61K41/0071C07F7/10
Inventor 黄剑东彭小慧郑碧远
Owner FUZHOU UNIV
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