Photosensitizer as well as preparation method and application for improving photodynamic performance of photosensitizer

A photosensitizer and reaction technology, applied in the field of photosensitizers, can solve problems such as difficulty in killing specific cancer cells, inability to exert photodynamic effects, and complex composition of nanoparticles, achieving strong tissue penetration, alleviating oxygen consumption, The effect of easy availability of raw materials

Inactive Publication Date: 2022-07-29
WEIFANG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] At present, photodynamic therapy for early cancers utilizes photosensitizers to convert surrounding oxygen into reactive oxygen species under the irradiation of light of a certain wavelength, and then kill cancer cells, with high spatiotemporal selectivity and high drug resistance. However, when Using a photosensitizer with photodynamic properties, when it mainly acts on tumor tissue, it cannot exert photodynamic effect, because the tumor tissue is severely hypoxic, and it is difficult to kill specific cancer cells under the required light waves
In the prior art, as a chemotherapeutic drug, lonidamine can inhibit the consumption of tumor cell oxygen, thereby alleviating the hypoxic situation of the tumor site, and further improving and enhancing the photodynamic effect of the photosensitizer. However, the photosensitizer and lonidamine At the same time, the metabolic pathways in the body are different, so the possibility of reaching the tumor site at the same time is almost zero. For the difficulties caused by this, it was proposed to construct nanoparticles, using the retention effect (EPR effect) and the high permeability of tumor blood vessels The photosensitizer and lonidamine are delivered to the tumor site at the same time, but the composition of the nanoparticles is quite complex and still cannot be completely degraded in the body, which brings a greater degree of side effects and is difficult to cure
[0003] The patent CN107266929B proposes a near-infrared fluorescent dye with a cyanine dye fluorescent group as the parent skeleton structure. The near-infrared red fluorescent dye prepared has a good biocompatibility. Water molecules, the principle of action is that the dye acts as a hydrophobic end and a hydrophilic molecule, and is connected with other molecules through a sensitive disulfide bond. As an application, it becomes a drug that integrates diagnosis and treatment with dual functions of treatment and imaging. As the parent, the middle substituent is selected to connect with the oxygen atom, but the photodynamic performance is still low

Method used

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  • Photosensitizer as well as preparation method and application for improving photodynamic performance of photosensitizer
  • Photosensitizer as well as preparation method and application for improving photodynamic performance of photosensitizer
  • Photosensitizer as well as preparation method and application for improving photodynamic performance of photosensitizer

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Effect test

Embodiment 1

[0070] The preparation method for improving the photodynamic performance of the photosensitizer CyBr-SS-L comprises the following steps:

[0071] (1) Add glacial acetic acid to the reaction flask, mix 4-bromophenylhydrazine hydrochloride and 3-methyl-2-butanone according to the molar ratio of 1:3, and then add it to the reaction flask, the temperature is 110 °C, and the time is 5h, the reaction was completed, the organic phase was extracted with ethyl acetate-water, the ethyl acetate was removed, and the organic layer was spin-dried to obtain product A, namely 5-bromo-2,3,3-trimethyl-3H-indium Indol;

[0072] (2) Prepare product A and ethyl iodide according to the molar ratio of 1:1, first add 5-bromo-2,3,3-trimethyl-3H-indole and ethyl iodide into the reaction flask, dissolve in adjacent In the dichlorobenzene solution, the reaction temperature was 160 °C, the reaction time was 12 h, and the temperature was lowered to room temperature; then suction filtration, washed with et...

Embodiment 2

[0086] The preparation method for improving the photodynamic performance of the photosensitizer CyI-SS-L comprises the following steps:

[0087] (1) Add glacial acetic acid to the reaction flask, mix 4-iodophenylhydrazine hydrochloride and 3-methyl-2-butanone according to the molar ratio of 1:2, and then add it to the reaction flask, the temperature is 80 °C, and the time is 12h, the reaction was completed, the organic phase was extracted with ethyl acetate-water, the ethyl acetate was removed, and the organic layer was spin-dried to obtain product A, namely 5-iodo-2,3,3-trimethyl-3H-indium Indol;

[0088] (2) Prepare product A and bromoethane in a molar ratio of 1:2, first add 5-iodo-2,3,3-trimethyl-3H-indole and bromoethane to the reaction flask and dissolve in toluene. In the solution, the reaction temperature was 130°C, the reaction time was 15h, and the temperature was lowered to room temperature; then suction filtration, washed with ethyl acetate, and dried to obtain pr...

Embodiment 3

[0102] The preparation method for improving the photodynamic performance of the photosensitizer CyH-SS-L comprises the following steps:

[0103] (1) Add glacial acetic acid to the reaction flask, mix phenylhydrazine hydrochloride and 3-methyl-2-butanone according to the molar ratio of 1:1, then add it to the reaction flask, the temperature is 100°C, the time is 9h, and the reaction After completion, the organic phase was extracted with ethyl acetate-water, the ethyl acetate was removed, and the organic layer was spin-dried to obtain product A, namely 2,3,3-trimethyl-3H-indole;

[0104] (2) Prepare product A and chloroethane in a molar ratio of 1:3, first add 2,3,3-trimethyl-3H-indole and chloroethane into the reaction flask, dissolve in acetonitrile solution, and react. The temperature was 80 °C, the reaction time was 20 h, and the temperature was lowered to room temperature; then suction filtration, washed with ethyl acetate, and dried to obtain product B, that is, the indole...

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Abstract

The invention belongs to the technical field of photosensitizers, and particularly relates to a photosensitizer and a preparation method and application for improving the photodynamic performance of the photosensitizer. The structural general formula of the prepared photosensitizer is shown in the specification, r1 is I, Br or H; x is I, Br or Cl; and R2 is a linear chain or branched chain alkyl group of C1-C6. According to the application of the photosensitizer provided by the invention, the photosensitizer is a near-infrared photosensitizer, is high in optical performance, can specifically target tumor cells, and meanwhile, has small and even no damage to normal cells; the defect that two different medicines, namely the photosensitizer and the lonidamine, have different metabolic pathways in vivo and are difficult to reach the tumor site at the same time is overcome; the invention further provides a preparation method of the near-infrared photosensitizer, raw materials are easy to obtain, reaction conditions are mild, and purification is easier.

Description

technical field [0001] The invention belongs to the technical field of photosensitizers, and particularly relates to a photosensitizer and a preparation method and application for improving the photodynamic performance of the photosensitizer. Background technique [0002] At present, photodynamic therapy for early stage cancer uses a photosensitizer that converts the surrounding oxygen into reactive oxygen species under light irradiation of a certain wavelength, and then kills cancer cells, with high spatiotemporal selectivity and high drug resistance. However, when When the photosensitizer with photodynamic properties is used, it cannot exert the photodynamic effect when it mainly acts on the tumor tissue, because the tumor tissue is severely hypoxic, and it is difficult to kill the specific cancer cells under the required light wave. In the prior art, as a chemotherapeutic drug, lonidamine can inhibit the consumption of oxygen in tumor cells, thereby relieving the hypoxia ...

Claims

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Application Information

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IPC IPC(8): C07D403/14A61K31/416A61K41/00A61K47/55A61P35/00
CPCC07D403/14A61K41/0057A61K31/416A61K47/55A61P35/00
Inventor 曹淑华台夕市李考学李法辉宋伟国王颖
Owner WEIFANG UNIVERSITY
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