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Preparation method and application of water-soluble cationic polyporphyrin

A technology of water-soluble cations and polyporphyrin, which is applied to medical preparations containing active ingredients, pharmaceutical formulas, photodynamic therapy, etc., can solve the problems of low dark toxicity, weakened PDT efficacy, and short cycle time, so as to improve biological compatibility effect

Inactive Publication Date: 2021-08-10
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Porphyrin derivatives are currently the most widely used in photodynamic therapy and have low dark toxicity. However, due to the planar rigid structure of porphyrin and the strong hydrophobic π-π stacking effect in aqueous media, with Increased concentration tends to aggregate, which in turn triggers aggregation-induced quenching, reduces singlet oxygen quantum yield, and impairs the efficacy of PDT
In addition, porphyrin 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 (Angew.Chem.Int.Ed.2019,58,2558-2569; Chem.Rev .2015,115,1990-2042)

Method used

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  • Preparation method and application of water-soluble cationic polyporphyrin
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  • Preparation method and application of water-soluble cationic polyporphyrin

Examples

Experimental program
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Embodiment 1

[0033] Embodiment 1: the synthesis of symmetrical type porphyrin monomer (porphyrin monomer 2)

[0034] Weigh methyl p-formylbenzoate (2g, 12.2mmol) and put it in a reaction flask, add pyrrole (4mL, 57.7mmol) dropwise with a needle, stir and dissolve, then add 100μL trifluoroacetic acid dropwise under nitrogen , Continue to stir the reaction at 50°C for 3h, and the reaction is terminated. Separation and purification by column chromatography to obtain the bipyrrole intermediate, the NMR is as follows figure 1 shown. The bipyrrole intermediate was treated and drained, and the bipyrrole intermediate (280.3mg, 1mmol) was weighed and placed in a reaction flask, and then 4-(trimethylsilyl)ethylbenzaldehyde (200mg, 1mmol) was weighed, added In the reaction flask, add 15 mL of dichloromethane to dissolve. After stirring and dissolving, 70 μL of trifluoroacetic acid was added with a needle under nitrogen gas, and the reaction system changed from yellow to deep purple after adding tr...

Embodiment 2

[0035] Embodiment 2: the synthesis of water-soluble cationic polyporphyrin

[0036] In the glove box, dissolve porphyrin monomer 2 (150mg, 0.2mmol) and diamine-based monomer (45mg, 0.2mmol) with thioketal bond in DMF, add 1-ethyl-(3- Dimethylaminopropyl) carbodiimide hydrochloride (EDC·HCl) (184mg, 0.96mmol) and 4-dimethylaminopyridine (DMAP) (96mg, 0.16mmol), reacted at 75°C for 48h, After the reaction was completed, the solvent was removed by rotary evaporation, and the linear polyporphyrin pPS was obtained by sedimentation and centrifugation purification; pPS (100 mg, 0.2 mmol alkynyl) was weighed and dissolved in DMF, and chlorine (pentamethylcyclopentadienyl) (cyclopentadienyl) was added. Octadiene)ruthenium(II)(Cp*Ru(COD)Cl)(3.8mg, 0.01mmol) and 0.6mmol cationic azide were reacted at 90°C for 48h. After the reaction was completed, the sedimentation centrifuged and washed with dichloromethane Water-soluble cationic polyporphyrin is obtained, and the NMR figure is as foll...

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Abstract

The invention belongs to the technical field of high polymer materials, biomedical materials and photodynamic therapy, provides a preparation method and application of water-soluble cationic polyporphyrin, and relates to a preparation method of water-soluble cationic polyporphyrin and application of water-soluble cationic polyporphyrin in photodynamic therapy of tumors. The invention provides the preparation method of water-soluble cationic polyporphyrin, and provides a technical reference for synthesizing a high-molecular-weight porphyrin polymer. Compared with monomer micromolecule porphyrin, the singlet oxygen yield of polyporphyrin can be increased to 1.5 times or above. Compared with monomer porphyrin, polyporphyrin has a potential photodynamic therapy effect. Compared with common polyporphyrin, the polyporphyrin has water solubility, and the biocompatibility of the polyporphyrin is improved.

Description

technical field [0001] The invention belongs to the technical field of polymer materials, biomedical materials and photodynamic therapy, and relates to a preparation method of water-soluble cationic polyporphyrin and its application in photodynamic therapy of tumors. Background technique [0002] Malignant tumors are the second leading cause of death in the world. The clinical treatment methods for malignant tumors mainly include surgical resection, chemotherapy and radiation therapy. These treatment methods have caused great side effects on patients. Different from traditional treatment methods, photodynamic therapy (Photodynamic therapy, PDT) is a treatment method that destroys or kills tumor cells by irradiating the tumor with light of a specific wavelength. It is non-invasive, highly selective, reproducible, and has toxic side effects. The advantages of small lights have become a new revolutionary treatment in recent years (Adv.Drug Deliv.Rev.2008,60,1627-1637; Chem.Soc....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G69/42C08G69/48A61K41/00A61P35/00
CPCA61K41/0057A61P35/00C08G69/42C08G69/48
Inventor 郑楠宋汪泽杜梦郑玉斌
Owner DALIAN UNIV OF TECH
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