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Preparation method of water-soluble polyporphyrin carrier-free nano-drug

A nano-drug, carrier-free technology, used in drug combinations, pharmaceutical formulations, medical preparations containing active ingredients, etc., can solve the problems of short circulation time, poor water solubility, and limited in vivo application, and achieve improved biocompatibility, Universal effect

Inactive Publication Date: 2021-12-10
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, since TPP is a planar rigid conjugated structure, due to the strong hydrophobic π-π stacking effect in aqueous media, as the concentration increases, the photosensitizer tends to aggregate, and it is easy to aggregate to cause aggregation-induced quenching (ACQ) effect, ACQ effect May greatly reduce the singlet oxygen quantum yield and impair the efficacy of photodynamic forces
In addition, TPP is a small molecule with poor water solubility, which is not conducive to drug administration, and has a short circulation time in the body. These problems limit its in vivo application.

Method used

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  • Preparation method of water-soluble polyporphyrin carrier-free nano-drug
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  • Preparation method of water-soluble polyporphyrin carrier-free nano-drug

Examples

Experimental program
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Effect test

Embodiment 1

[0023] Embodiment 1: the synthesis of water-soluble polyporphyrin P-3O

[0024] Accurately weigh tetracarboxyphenylporphyrin (25mg, 0.032mmol), EDCI (49mg, 0.256mmol) and DMAP (15.6mg, 0.128mmol) and dissolve in 0.2mL-2mL DMF, heat to 60°C-80°C and stir for 10min. Then, a mixed solution of tetraethylene glycol (12.4mg, 0.064mmol) and 0.1mL-0.5mL of DMF was added, and the temperature was raised to 100°C-140°C to continue the reaction for 24h-48h. After the reaction was completed, the reaction solution was settled in 15 mL of ether, the precipitate was collected by centrifugation, and the remaining ether was removed by vacuum drying overnight. Dissolve the precipitate in H at a volume ratio of 10:1 2 In a mixed solvent of O and DMSO, and dialyzed in deionized water for 24 h with a dialysis bag with a molecular weight cut-off (MWCO) of 500, and then freeze-dried in a freeze dryer, the final product was purple solid P-3O. The proton spectrum NMR characterization of gained polypo...

Embodiment 2

[0025] Embodiment 2: the synthesis of water-soluble polyporphyrin P-5O

[0026] Accurately weigh tetracarboxyphenylporphyrin (25mg, 0.032mmol), EDCI (49mg, 0.256mmol) and DMAP (15.6mg, 0.128mmol) and dissolve in 0.2mL-2mL DMF, heat to 60°C-80°C and stir for 10min. Then, a mixed solution of hexaethylene glycol (17.6mg, 0.064mmol) and 0.1mL-0.5mL DMF was added, and the temperature was raised to 100°C-140°C to continue the reaction for 24h-48h. After the reaction was completed, the reaction solution was settled in 15 mL of ether, the precipitate was collected by centrifugation, and the remaining ether was removed by vacuum drying overnight. Dissolve the precipitate in H at a volume ratio of 10:1 2 In a mixed solvent of O and DMSO, and dialyzed in deionized water for 24 h with a dialysis bag with a molecular weight cut-off (MWCO) of 500, and then freeze-dried in a freeze dryer, the final product was a purple solid P-5O. The proton spectrum NMR characterization of gained polyporp...

Embodiment 3

[0027] Embodiment 3: the synthesis of water-soluble polyporphyrin P-11O

[0028] Accurately weigh tetracarboxyphenylporphyrin (25mg, 0.032mmol), EDCI (49mg, 0.256mmol) and DMAP (15.6mg, 0.128mmol) and dissolve in 1mL chloroform, heat to 60°C-80°C and stir for 10min. Then, a mixed solution of polyethylene glycol (32 mg, 0.064 mmol) with a molecular weight of 500 Da and 1 mL of chloroform was added, and the temperature was raised to 70° C. to continue the reaction for 24h-48h. After the reaction was completed, the reaction liquid was settled in 30 mL of n-hexane, the precipitate was collected by centrifugation, and the remaining n-hexane was removed by vacuum drying overnight. Dissolve the precipitate in 1 mL H 2 O, and dialyzed in deionized water for 24 h with a molecular weight cut-off (MWCO) bag of 1000, and then freeze-dried in a freeze dryer, the final product was purple solid P-11O.

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Abstract

The invention belongs to the technical field of high polymer materials, biomedical materials and photodynamic and sonodynamic therapy, and provides a preparation method of a water-soluble polyporphyrin carrier-free nano-drug. The number-average molecular weight of the water-soluble polyporphyrin carrier-free nano-drug prepared by the preparation method disclosed by the invention ranges from 5000g / mol to 30000g / mol, the solubility of the water-soluble polyporphyrin carrier-free nano-drug in water can reach 50mg / mL, and the singlet oxygen yield of the water-soluble polyporphyrin carrier-free nano-drug is 1.5-3 times that of tetracarboxyphenyl porphyrin. The polymer can be directly dissolved in water, and can spontaneously form stable nanoparticles in a carrier-free form within the concentration range of 0.01 mg / mL to 10 mg / mL, and the particle size range is 100 nm to 200 nm. Compared with common polyporphyrin, the polyporphyrin has the advantages that water solubility is realized, and the biocompatibility is improved. The polyporphyrin can be self-assembled into nano-particles in water, other carriers are not needed, and a potential in-vivo delivery effect is achieved.

Description

technical field [0001] The invention belongs to the technical field of polymer materials, biomedical materials and photodynamic and acoustodynamic therapy, and relates to a preparation method of water-soluble polyporphyrin and its application in photoacoustic dynamic therapy of tumors. Background technique [0002] Cancer is one of the leading causes of morbidity and death in the world. Traditional tumor treatment methods include surgical resection, radiotherapy and chemotherapy, which can achieve the effect of treating tumors to a certain extent, but have the advantages of easy recurrence, large toxic and side effects, and options Disadvantages such as poor sex and invasiveness. Compared with the traditional methods of treating tumors, photodynamic therapy and sonodynamic therapy are new, non-invasive methods for treating tumors. They are characterized by less toxic and side effects, reproducibility, good selectivity, and non-invasive or minimally invasive. Potential new m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/333C08G65/48C07D487/22A61K9/14A61K41/00A61P35/00
CPCC08G65/33396C08G65/48C07D487/22A61K41/0071A61K41/0033A61K9/14A61P35/00
Inventor 郑楠宋汪泽杜梦郑玉斌
Owner DALIAN UNIV OF TECH
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