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Photosensitizer with high singlet oxygen yield and preparation method thereof

A singlet oxygen and photosensitizer technology, applied in the field of photosensitizers, can solve problems such as hindering the development of photodynamic therapy and low singlet oxygen yield, and achieve the effects of long triplet excited state lifetime, stable structure and stable fluorescence performance.

Active Publication Date: 2021-02-19
SHANDONG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, although these current strategies have improved the singlet oxygen yield of photosensitizer molecules to a certain extent, the yield of singlet oxygen is still relatively low, and it is necessary to increase the dose to achieve the purpose of treating tumors, which is extremely difficult. Large obstacles hinder the development of photodynamic therapy in the field of cancer treatment

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  • Photosensitizer with high singlet oxygen yield and preparation method thereof
  • Photosensitizer with high singlet oxygen yield and preparation method thereof
  • Photosensitizer with high singlet oxygen yield and preparation method thereof

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Embodiment Construction

[0023] The following will clearly and completely describe the technical solutions in the embodiments of the present invention with reference to the drawings in the embodiments of the present invention.

[0024] The invention provides a photosensitizer with high singlet oxygen production rate, its structural formula is as follows:

[0025]

[0026] The preparation method of above-mentioned photosensitizer is as follows:

[0027] In the vacuum reaction bottle, pass through N for about 15 minutes. 2 , to ensure an oxygen-free environment in the vacuum reaction bottle, in the presence of N 2 Add a mixed solution of 20mL toluene solution and 5mL water into the vacuum reaction bottle as the reaction solvent, and then pass through the long needle tube to pass in N for about 20 minutes. 2 to remove oxygen from the solvent.

[0028] Join K first 2 CO 3 (129.7mg, 0.868mmol) The solid powder provides an alkaline environment, and then 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-y...

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Abstract

The invention discloses a photosensitizer with high singlet oxygen yield and a preparation method thereof. 4, 8-dibromo-6-(2-ethylhexyl)-[1, 2, 5] thiadiazole [3, 4-F] benzotriazole and 4- (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborane-2-yl) pyridine are subjected to a Suzuki coupling reaction under the catalysis of a [1, 1'-bis (diphenylphosphino) ferrocene] palladium dichloride, and oxidation addition and reduction elimination are performed to obtain the photosensitizer. The photosensitizer disclosed by the invention has relatively strong absorption capability in visible light, is stable in structure under the condition of slight acid to weak base, has very high quantum yield and high singlet oxygen generation capability, and can be applied to fluorescence imaging or photodynamic therapy oftumors as a novel photosensitizer.

Description

technical field [0001] The invention relates to a photosensitizer, in particular to a photosensitizer with high singlet oxygen yield and a preparation method thereof. Background technique [0002] Traditional cancer treatments such as chemotherapy, surgery, and radiotherapy have strong side effects, such as damage to normal cells and the nervous system, and are often accompanied by a high recurrence rate. Therefore, developing a safe and effective cancer treatment is an urgently needed research topic. In recent years, photodynamic therapy has attracted extensive attention due to its low toxicity, wide anti-tumor selectivity and minimal invasiveness. The main building block in photodynamic therapy is the photosensitizer molecule. Among them, the photosensitizer absorbs light from a specific wave source (visible light or near-infrared) and is excited from the ground state to the singlet excited state, and then undergoes an intersystem crossing process to transform into a tri...

Claims

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Application Information

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IPC IPC(8): C07D513/04C09K11/06A61K41/00A61P35/00
CPCC07D513/04C09K11/06A61K41/0057A61P35/00C09K2211/1081C09K2211/1029
Inventor 吕世博苗钰阳刘大鹏宋锋玲
Owner SHANDONG UNIV
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