Medicine for photodynamic therapy and chemotherapy of cancer and preparation method thereof

A technology of photodynamic therapy and photodynamic therapy, applied in the field of medicine, to achieve the effect of single molecular weight distribution, easy control and use, and avoid π-π stacking and aggregation

Active Publication Date: 2019-03-19
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, most of the reported porphyrin derivatives have greatly reduced π-π stacking due to large planar structures. 1 o 2 generation, inhibiting the PDT efficiency
This aggregation produces low singlet oxygen concentration under hypoxic conditions and has become one of the common limitations that limit the ability of porphyrin derivatives and other photosensitizing drugs to achieve PDT function in potential clinical applications.

Method used

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  • Medicine for photodynamic therapy and chemotherapy of cancer and preparation method thereof
  • Medicine for photodynamic therapy and chemotherapy of cancer and preparation method thereof
  • Medicine for photodynamic therapy and chemotherapy of cancer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Synthesis of PDP

[0051]

[0052] Weigh 16.2 μmol of 5,10,15,20-tetrakis(3-pyridyl)porphyrin (P) and 4,4'-bis(trans-bis(triethylphosphine)(trifluoromethane)platinum) Benzophenone (DP) 32.4 μmol, the above substances were dissolved in dimethyl sulfoxide, reacted at 80 ° C for 12 h, after cooling to room temperature, an excess of diethyl ether was added to form a precipitate, filtered, washed with ether, It was then dried in vacuo to give a dark brown solid (51.5 mg, 96.4%).

[0053] 1 H NMR (δppm): δ9.60(m,8H,Py-H a ),δ9.33(d,8H,Py-H b ),δ8.94 (m,24H,Py-H d ,P-H e ),δ8.28(t,8H,Py-H c ),δ7.63(d,16H,Ph-H 2 ),δ 7.20-7.30(m,16H,Ph-H 1 ),δ-3.13(s,4H,P-H f ).

[0054] 31 P{1H}NMR: δ=12.64ppm

[0055] ESI-MS ( figure 1 (A)): 6600Da

[0056] 2D correlation spectrum (2D COZY) ( figure 2 (A))

Embodiment 2

[0058] Synthesis of ZPDP

[0059]

[0060] Weigh 14.7 μmol of zinc 5,10,15,20-tetrakis(4-pyridyl)-21H, 23H-porphyrin (ZP) and 4,4'-bis(trans-bis(triethylphosphine) (tri Fluoromethane) platinum) benzophenone (DP) 29.4 μmol, the above substances were dissolved in dimethyl sulfoxide, reacted at 80 ° C for 12 h, after cooling to room temperature, an excess of diethyl ether was added to form a precipitate, Filtration, washing with ether, and drying in vacuo gave a purple-black solid (47.0 mg, 95.1%).

[0061] 1 H NMR: δ9.60(s,8H,Py-H a ),δ9.29-9.30(d,8H,Py-H b ),δ8.84-8.87 (m,24H,Py-H d ,ZP-H e ),δ8.22-8.25(t,8H,Py-H c ),δ7.64(d,16H,Ph-H 2 ),δ 7.21-7.32(m,16H,Ph-H 1 )

[0062] 31 P{1H}NMR: 12.73ppm

[0063] ESI-MS ( figure 1 (B)): 6732Da

[0064] 2D correlation spectrum (2D COZY) ( figure 2 (B))

Embodiment 3

[0066] Preparation of supramolecular cage-loaded nanoparticles

[0067] Preparation of Supramolecular Cage-loaded Nanoparticles PDP NPs and ZPDP NPs

[0068] Add 5 mL of acetone solution containing 6.0 mg of supramolecular cage (PNP or ZPNP), mPEG-b-PEBP (25.0 mg) and RGD-PEG-b-PEBP (5.0 mg) dropwise into 20 mL of Milli-Q water and stir vigorously , vacuum dried. After 5 minutes of sonication, a well-dispersed nanoparticle suspension was obtained.

[0069] The morphology and size of the nanoparticles were studied by transmission electron microscopy (TEM) and dynamic laser scattering (DLS), see image 3 ,As can be seen, image 3 As shown in A, spherical PDP NPs with diameters ranging from 30 to 90 nm were observed in the dry state. Due to the hydration of NP, from DLS( image 3 B) A slightly larger hydrophilic diameter is noted. An increase in diameter from 35.7 nm to 61.8 nm was observed after loading the PDP cage into NPs, indicating that the amphiphilic polymer success...

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Abstract

The invention provides a method of preparing nanoparticles loaded on supramolecular cages. The nanoparticles are used for the photodynamic therapy and chemotherapy of the cancer. The method comprisesthe following steps of: step 1. preparing supramolecular cages required by the nanoparticles; and step 2. introducing mPEG-b-PEBP and RGD-PEG-b-PEBP to form the nanoparticles together with the supramolecular cages, wherein the supramolecular cages comprise tetrapyridylporphyrin derivatives or tetrapyridine metalloporphyrin derivatives and Pt(II) receptors. The nanoparticles located on the supramolecular cages can be stably and persistently present in the inner circulation of a living body, have a targeting effect on cancerous tissues and facilitate drug transportation and cancer treatment.

Description

technical field [0001] The invention belongs to the technical field of medicine, relates to a medicine for treating cancer, in particular to a medicine for photodynamic therapy and chemotherapy of cancer and a preparation method thereof. Background technique [0002] Over the past decades, photodynamic therapy (PDT) has proven to be an attractive and promising clinical approach for the treatment of lung, bladder, skin, and esophageal cancers. PDT is the photosensitive drug (PS) is activated by light of appropriate wavelengths to generate reactive oxygen species (ROS), which can damage cellular compartments including plasma, mitochondria, lysosomes, and nuclei, resulting in irreversible damage to cells. resulting in the death of cancer cells. Compared with traditional treatment methods, PDT shows several obvious advantages, such as non-invasive treatment, controllable time, negligible drug resistance and low toxic side effects. Among the many photosensitive drugs that may h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/69A61K47/60A61K41/00A61P35/00A61K31/282
CPCA61K31/282A61K41/0071A61K41/0076A61K47/60A61K47/6949A61P35/00A61K2300/00
Inventor 王明蒋鑫于浩曾云婷
Owner JILIN UNIV
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