A photosensitizer with tumor targeting and its preparation method and application

A tumor targeting and photosensitizer technology, applied in the field of biomedicine, can solve the problems of poor water solubility, unstable structure, and no specific targeting of DPP derivative photosensitizers, and achieves excellent water solubility, simple preparation process, excellent Effects of water solubility and tumor targeting

Active Publication Date: 2018-08-10
南京基树医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The main purpose of the invention is to solve the defects of existing DPP derivative photosensitizers such as poor water solubility, no specific targeting, and unstable structure, and provide a new type of photosensitizer for targeted photodynamic therapy of tumors

Method used

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  • A photosensitizer with tumor targeting and its preparation method and application
  • A photosensitizer with tumor targeting and its preparation method and application
  • A photosensitizer with tumor targeting and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0038]Synthesis of 3,6-bis(2-thienyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione covalently bound to hyaluronic acid (DTDPP-H-HA) :

[0039] Under nitrogen protection, starting material 3,6-bis(2-thienyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione (1.24g, 5.0mmol), starting material 1 , 6-dibromohexane (6.02g, 12mmol) and raw material anhydrous potassium carbonate (0.52g, 9.28mmol) were added in 25ml DMF, stirred at 55°C for 20h, washed with water, extracted with DCM to remove DMF to obtain crude product, crude The product was separated by silica gel column to obtain the red intermediate DTDPP-A.

[0040] Under the protection of nitrogen, the raw materials tetrabutylammonium hydroxide (2.98g, 29mmol) and sodium hyaluronate (1.16g, 2.8mmol) were added to deionized water, stirred at 40°C for 15h, and freeze-dried to obtain the intermediate HA - .

[0041] Under the protection of nitrogen, the intermediate 3,6-bis(2-thienyl)-2,5-bis(1-bromo-hexane)pyrrolo[3,4-c]pyrrole-1,4 obt...

Embodiment 2

[0047] 3,6-bis(2-bromo-thienyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione covalently bound to hyaluronic acid (DTDPP-Br-HA) Synthesis:

[0048] Under nitrogen protection, raw material 3,6-bis(2-bromo-thienyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione (DTDPP-Br) (2.04g , 5.0mmol), raw material 1,6-dibromohexane (7.525g, 15mmol) and raw material anhydrous potassium carbonate (0.84g, 15mmol) were added to 25ml anhydrous DMF, stirred at 70°C for 15h, washed with water, washed with DCM DMF was removed by extraction to obtain a crude product, which was separated by silica gel chromatography to obtain a red intermediate DTDPP-B.

[0049] Under the protection of nitrogen, the raw material tetrabutylammonium hydroxide (2.98g, 29mmol) and the raw material sodium hyaluronate (1.16g, 2.8mmol) were added to deionized water, stirred at 45°C for 10h, and freeze-dried to obtain the intermediate HA - .

[0050] Under nitrogen protection, the red intermediate 3,6-bis(2-bromo-thienyl)-2,5-b...

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Abstract

The invention discloses a photosensitizer with tumor targeting and a preparation method and applications thereof. The photosensitizer disclosed by the invention is synthesized mainly through the covalent binding of 3,6-di(2-thienyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione and a derivative thereof and hyaluronic acid. The novel photosensitizer has good singlet oxygen producing ability, excellent water solubility and targeting-specific tumor cells, so that after being applied to the photodynamics therapy of tumor cells and living bodies, the photosensitizer can effectively kill the tumor cells, therefore, the photosensitizer as a photodynamic tumor therapy photosensitizer has a good application prospect. Moreover, the compound structure of the photosensitizer disclosed by the invention is explicit, and a preparation process is simple and feasible.

Description

technical field [0001] The invention belongs to the field of biomedicine, and in particular relates to a novel photosensitizer with tumor targeting, a preparation method thereof and application of targeted photodynamic therapy to tumors. Background technique [0002] Cancer, also known as malignant tumor, is the number one killer of human life and health. Data from the 2014 World Cancer Report shows that global cancer cases will increase rapidly, from 14 million in 2012 to 19 million in 2025. Current cancer treatment mainly includes: surgical resection, chemotherapy and radiotherapy. However, these therapies have obvious side effects, such as: surgery needs to accurately locate the tumor location, while chemotherapy and radiotherapy damage normal cells at the same time, which is a huge harm to the patient. Therefore, developing more effective cancer treatments has attracted numerous research interests. [0003] Photodynamic therapy (PDT) is a new tumor treatment technolog...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K41/00A61K47/61A61P35/00
Inventor 董晓臣张琪蔡宇唐倩云黄维
Owner 南京基树医药科技有限公司
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