Coordination driven self-assembling supramolecular cage as well as preparation method and application thereof

A self-assembly, supramolecular technology, applied in the field of medicine, to achieve the effect of improving efficiency, increasing chemotherapeutic ability, and being easy to control and use

Active Publication Date: 2019-04-26
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 photosensitizers to achieve PDT function in potential clinical applications.

Method used

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  • Coordination driven self-assembling supramolecular cage as well as preparation method and application thereof
  • Coordination driven self-assembling supramolecular cage as well as preparation method and application thereof
  • Coordination driven self-assembling supramolecular cage as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Synthesis of PDP

[0049]

[0050]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%).

[0051] 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 ).

[0052] 31 P{1H}NMR: δ=12.64ppm

[0053] ESI-MS ( figure 1 (A)): 6600Da

[0054] 2D correlation spectrum (2D COZY) ( figure 2 (A))

Embodiment 2

[0056] Synthesis of ZPDP

[0057]

[0058] 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%).

[0059] 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 )

[0060] 31 P{1H}NMR: 12.73ppm

[0061] ESI-MS ( figure 1 (B)): 6732 Da

[0062] 2D correlation spectrum (2D COZY) ( figure 2 (B))

Embodiment 3

[0064] Preparation of supramolecular cage-loaded nanoparticles

[0065] Preparation of Supramolecular Cage-loaded Nanoparticles PDP NPs and ZPDP NPs

[0066] 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.

[0067] 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 NPs, 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 succes...

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Abstract

The invention provides a coordination driven self-assembling supramolecular cage. The supramolecular cage comprises tetrapyridine porphyrin derivatives or tetrapyridine metalloporphyrin derivatives and Pt(II) receptors. Compared with structures such as an MOF (metal-organic framework), nanoparticles and the like, the coordination driven self-assembling supramolecular cage has a quite special and unique structure, has single molecular weight distribution and is easier to control and use. By means of the Pt(II) receptors in the structure, the tetrapyridine porphyrin derivatives are distributed on the two sides, porphyrin aggregation is greatly reduced, Pi-Pi accumulation and aggregation of porphyrin are avoided, and production efficiency of <1>O2 is effectively improved. The tetrapyridine porphyrin derivatives or the tetrapyridine metalloporphyrin derivatives in the supramolecular cage are taken as a PDT (photodynamic therapy) photosensitizer and donors, and the Pt(II) receptors are taken as chemotherapeutic receptors. With introduction of the Pt(II) receptors, not only can chemotherapeutic capacity of a drug be improved, but also higher synergistic anticancer efficiency can be realized with the PDT by enabling the Pt(II) receptors to enter the precise supramolecular cage.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to a supramolecular cage, a preparation method and application thereof, in particular to a coordination-driven self-assembled supramolecular cage, a preparation method and application 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 a photosensitizer (PS) that is activated by light of an appropriate wavelength to generate reactive oxygen species (ROS) to induce cancer cell death. 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 many photosensitizers that may have PDT function, porphyrin and its derivatives have received special attention. Therefore, scientific resea...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C07F19/00A61K31/282A61P35/00A61K41/00
CPCA61K41/0057A61P35/00C07F15/0086
Inventor 王明蒋鑫于浩曾云婷
Owner JILIN UNIV
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