A kind of preparation method and application of polyporphyrin compound

A compound, polyporphyrin technology, applied in the field of preparation of polyporphyrin compounds, can solve the problem of low drug loading, achieve the effect of improving phototoxicity and singlet oxygen yield

Active Publication Date: 2021-01-19
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The invention mainly solves the self-quenching effect caused by the agglomeration of hydrophobic porphyrin drugs, and at the same time overcomes the problem of low drug loading of photosensitizer nano-medicines

Method used

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  • A kind of preparation method and application of polyporphyrin compound
  • A kind of preparation method and application of polyporphyrin compound
  • A kind of preparation method and application of polyporphyrin compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1: the synthesis of polyporphyrin photosensitizer (pPS)

[0027] Dissolve tetraphenylporphyrin modified with four functional groups in tetrahydrofuran (0.5M, 1.0eq), add thioketal-containing comonomer with 2-terminal difunctional group of raw material into the reaction system (2.0eq), add 1-ethane Base-(3-dimethylaminopropyl)carbodiimide hydrochloride (4.8eq) and 4-dimethylaminopyridine (0.8eq), warm up to 50°C, react for 24h, and wait for the reaction bottle to cool to room temperature Carry out settling centrifugation 3 times with ether afterward, crude product is in dialysis bag (molecular weight cut-off 500) with deionization dialysis, lyophilization, the polymerization product pPS that obtains, group 1,2,3 are respectively the mol ratio of carboxylic acid / amino group is 0.8, 1, and 1.2, the molecular weight and distribution are shown in Table 1, and the NMR characterization is as follows figure 1 shown.

[0028] Table 1. Molecular weight and zeta poten...

Embodiment 2

[0030] Embodiment 2: the photodegradation experiment of polyporphyrin photosensitizer (pPS):

[0031] Polymer pPS (20mg) was dissolved in d-DMSO, using a 650nm laser (140mW / cm 2 ) light for 20 minutes, judged by the acetone peak at 2.1ppm in NMR that photodegradation of pPS has taken place, such as figure 2 shown.

Embodiment 3

[0032] Embodiment 3: Preparation of polyporphyrin photosensitizer nanomaterials (PEG-pPS and HA-pPS):

[0033] The polymer pPS was dissolved in deionized water (1 mg / mL), and PEG-COOH (1 mg / mL) and HA (1 mg / mL) were added to the pPS aqueous solution in various ratios (10 / 1-1 / 5) middle. The mixture was mixed at 37°C for 1 hour, and its particle size and shape were observed by scanning electron microscopy, as shown in image 3 As shown, the particle diameters of the two kinds of particles are both 100-200nm, and the morphology is spherical. Subsequently, the particle size changes in PBS buffer (pH 5.8, 6.8 and 8.0) of different pH values ​​were measured by dynamic light scattering, as Figure 4 As shown in a, the particles have good stability and the particle size changes little. Subsequently, the particles were diluted in different times (1-10 times), and the particle size change was measured, such as Figure 4 As shown in b, the results show that the particle stability is ...

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Abstract

The invention belongs to the technical field of high polymer materials, biomedical materials and photodynamic therapy, and relates to a preparation method and application of a polymeric porphyrin compound. The preparation method comprises the following steps: dissolving tetracarboxylic acid modified tetraphenylporphyrin in an organic solvent, wherein the concentration is 0.1-1M; adding a thioketalcomonomer with terminal diamino into a reaction system, and finally adding 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride and 4-dimethylaminopyridine; heating the reaction system to 50-100 DEG C, and reacting for 24-72 hours; and after the reaction is finished, cooling to room temperature, settling and centrifuging, dialyzing an obtained crude product by using deionized water, and freeze-drying to obtain the polymeric porphyrin compound pPS.

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 and application of polyporphyrin compounds. Background technique [0002] Photodynamic therapy (PDT) is currently a revolutionary high-tech biological treatment method for malignant tumors. In the past ten years, PDT has attracted much attention in the field of cancer treatment (Adv.Drug Deliv.Rev.2008,60 , 1627-1637; Chem.Soc.Rev.2011, 40, 340-362; Chem.Soc.Rev.2016, 45, 6597-6626). Compared with the traditional three major cancer treatment methods such as surgery, radiotherapy and chemotherapy, PDT has achieved good targeting selectivity and tissue specificity for tumor cells, and has the advantages of mild trauma, less toxic side effects, and repeatable phototherapy. , so it has great advantages. [0003] So far, most of the photosensitizers that have been put into experimental research and clinical ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G69/42A61K41/00A61P35/00
CPCA61K41/0071A61P35/00C08G69/42
Inventor 郑楠张芷伊谢丹宋汪泽郑玉斌
Owner DALIAN UNIV OF TECH
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