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Amorphous MOF nano photosensitizer as well as preparation method and application thereof

A photosensitizer, amorphous technology, applied in the field of photosensitive materials, can solve problems such as limited penetration depth and irradiation area, difficult to obtain therapeutic effect, and reduced ROS generation, achieve good long-term stability, improve bioavailability, and improve Effect of PDT effect

Active Publication Date: 2022-07-26
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, at present, PS generally has problems such as poor water solubility, easy photobleaching, lack of targeting, and oxygen dependence, which restricts the clinical application of PDT and makes it difficult to achieve ideal therapeutic effects.
For example: (1) most PSs are hydrophobic compounds, which lead to aggregation, fluorescence quenching, and reduced ROS generation in aqueous solution; (2) due to lack of targeting, the content of PS at the tumor site may be insufficient after systemic administration; (3 ) The uncontrolled proliferation of cancer cells leads to hypoxia in tumor tissue, which is not conducive to the formation of reactive oxygen species. In addition, PDT consumes O 2 Further aggravate the hypoxia, causing a vicious cycle; (4) Due to the limited penetration depth and irradiation area of ​​light, PDT is not suitable for deep tumors and metastatic tumors

Method used

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  • Amorphous MOF nano photosensitizer as well as preparation method and application thereof
  • Amorphous MOF nano photosensitizer as well as preparation method and application thereof
  • Amorphous MOF nano photosensitizer as well as preparation method and application thereof

Examples

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Embodiment 1

[0059] Embodiment 1 Near-infrared photosensitizer (BDP-I 8 ) preparation

[0060] The present embodiment relates to a near-infrared photosensitizer BDP-I 8 The synthesis of , its synthetic route is as figure 1 shown, including the following steps:

[0061] (1) Synthesis of compound 1: 3,5-diiodo-p-hydroxybenzaldehyde and bromopropyne were added to the reaction vessel in a molar ratio of 1:3, then potassium carbonate in a molar ratio of 1:1 with bromopropyne was added, and then added Acetonitrile 50mL was stirred at 80°C for 12h. After the reaction, extract with dichloromethane and water, collect the organic layer, and concentrate on a rotary evaporator to obtain a crude product. The crude product is separated by silica gel column chromatography (eluent is petroleum ether-dichloromethane system) to obtain Compound 1, 85% yield.

[0062] (2) Synthesis of compound 2: Compound 1 and 2,4-dimethylpyrrole were added to the reaction vessel in a molar ratio of 1:2, and then tetrah...

Embodiment 2

[0066] Example 2 BDP-I 8 preparation

[0067] The present embodiment relates to a near-infrared photosensitizer BDP-I 8 The synthesis of , its synthetic route is as figure 1 shown, including the following steps:

[0068] (1) Synthesis of compound 1: 3,5-diiodo-p-hydroxybenzaldehyde and bromopropyne were added to the reaction vessel in a molar ratio of 1:5, then potassium carbonate in a molar ratio of 1:1 with bromopropyne was added, and then added Acetonitrile 80 mL was stirred at 60 °C for 12 h. After the reaction, extract with dichloromethane and water, collect the organic layer, and concentrate on a rotary evaporator to obtain a crude product. The crude product is separated by silica gel column chromatography (eluent is petroleum ether-dichloromethane system) to obtain Compound 1, 70% yield.

[0069] (2) Synthesis of compound 2: Compound 1 and 2,4-dimethylpyrrole were added to the reaction vessel in a molar ratio of 1:3, and then tetrahydrofuran 100 times the weight of...

Embodiment 3

[0073] Example 3 BDP-I 8 preparation

[0074] The present embodiment relates to a near-infrared photosensitizer BDP-I 8 The synthesis of , its synthetic route is as figure 1 shown, including the following steps:

[0075] (1) Synthesis of compound 1: 3,5-diiodo-p-hydroxybenzaldehyde and bromopropyne were added to the reaction vessel in a molar ratio of 1:6, then potassium carbonate in a molar ratio of 1:2 with bromopropyne was added, and then added Acetonitrile 50mL was stirred at 80°C for 12h. After the reaction, extract with dichloromethane and water, collect the organic layer, and concentrate on a rotary evaporator to obtain a crude product. The crude product is separated by silica gel column chromatography (eluent is petroleum ether-dichloromethane system) to obtain Compound 1, 80% yield.

[0076](2) Synthesis of compound 2: Compound 1 and 2,4-dimethylpyrrole were added to the reaction vessel in a molar ratio of 1:4, and then tetrahydrofuran 100 times the weight of 2,4...

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Abstract

The invention discloses an amorphous MOF nano photosensitizer as well as a preparation method and application thereof. The preparation method comprises the following steps: firstly, by taking BODIPY as a mother nucleus, preparing a near-infrared photosensitizer through polyiodization and polycarboxylation derivation; the MOF nano photosensitizer with photodynamic activity is constructed by taking the near-infrared photosensitizer as a ligand and coordinating with metal ions. The prepared MOF nano photosensitizer is in an amorphous state, has good water solubility and shows efficient photodynamic activity under the illumination condition, and the photodynamic effect of the MOF nano photosensitizer is verified on the cell and animal level. Besides, the maximum absorption wavelength and emission wavelength of the amorphous MOF nano photosensitizer prepared by the invention are both located in a near-infrared region, so that deep tumor treatment by adopting near-infrared light is facilitated, and the amorphous MOF nano photosensitizer has a good application prospect.

Description

technical field [0001] The invention relates to the technical field of photosensitive materials, in particular to an amorphous MOF nano-photosensitizer and a preparation method and application thereof. Background technique [0002] Photodynamic therapy (PDT) is an emerging tumor treatment method. It has achieved good therapeutic effects in the treatment of skin cancer, nasopharyngeal cancer and breast cancer. It has the advantages of good tropism, not easy to relapse, and not easy to develop drug resistance. PDT specifically refers to the injection of a special chemical substance, that is, photosensitizer (PS), into the body of tumor patients and accumulation in tumor tissue. 2 In the presence of light, the photosensitizer reacts with ground state oxygen to generate reactive oxygen species (ROS) after being irradiated by light of a specific wavelength, and uses reactive oxygen species to effectively kill tumor tissues, thereby causing local tumor cell death. Therefore, pho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C08G83/00A61K41/00A61P35/00
CPCC07F5/022C08G83/008A61K41/0057A61P35/00Y02A50/30
Inventor 郭正清李红宇何慧徐晗黄阳阳纪丹丹
Owner SUZHOU UNIV
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