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Method for activating anti-tumor compound through biological orthogonal photocatalytic oxidative dehydrogenation, composition and application

A photocatalytic oxidation and bioorthogonal technology, applied in the field of medical materials, can solve the problems of the need to improve the activation efficiency and the activation wavelength is short, and achieve the effect of excellent anti-cancer effect, long excitation wavelength and high photoactivation efficiency.

Pending Publication Date: 2021-12-21
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method has shortcomings such as short activation wavelength and activation efficiency.

Method used

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  • Method for activating anti-tumor compound through biological orthogonal photocatalytic oxidative dehydrogenation, composition and application
  • Method for activating anti-tumor compound through biological orthogonal photocatalytic oxidative dehydrogenation, composition and application
  • Method for activating anti-tumor compound through biological orthogonal photocatalytic oxidative dehydrogenation, composition and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Dihydrophenanthridine alkaloids are compound I-1 (dihydrochelerythrine); compound I-1 is prepared by reducing chelerythrine hydrochloride:

[0058] Chemical I-1: Dihydrochelerythrine, structural formula:

[0059]

[0060] Chelidonium hydrochloride, structural formula:

[0061]

[0062] Dihydrochelerythrine can be prepared by reduction of chelerythrine hydrochloride: the compound chelerythrine hydrochloride (100mg, 0.25mmols) was dissolved in 15mL methanol solution, and sodium borohydride (80mg, 2.16mmols) was added , after 30 minutes of stirring in the dark at room temperature, stop the reaction, spin evaporate, wash the solid with ultrapure water, centrifuge and discard the supernatant, repeat the washing and centrifugal operation three times, dry in vacuo, and obtain the white solid product dihydrochelerythrine (90mg , yield: 90%).

Embodiment 2

[0064] Screening of photocatalysts for photocatalytic oxidative dehydrogenation:

[0065] Add compound I-1 (dihydrochelerythrine) and photocatalyst 111 to the solution of water: dimethyl sulfoxide (99:1, v / v) respectively, irradiate with desk lamp (white light), and in air The irradiation time is 30 minutes to obtain dehydrogenation compound II-1 (chelerythrine).

[0066] Photocatalyst III is used as a catalyst for photocatalytic oxidative dehydrogenation reaction, and photocatalyst III is more than one of the following compounds;

[0067]

[0068] Preferably, the photocatalyst is riboflavin (III-1):

[0069]

[0070] The structure of the dehydrogenation compound is formula II-1:

[0071]

[0072] After photooxidative dehydrogenation of compound I-1, the dehydrogenated compound is formula II-1, X - Provides anions for the medium.

Embodiment 3

[0074] Using riboflavin (III-1) as a photocatalyst, the photophysical properties of compound I-1 (dihydrochelerythrine) transformed into dehydrogenated compounds were characterized:

[0075] figure 1 It is the ultraviolet-visible absorption spectrogram of compound I-1, II-1 (chelerythrine hydrochloride) and III-1 in the buffer solution, and the mixture of I-1 and III-1 changes with time in different pH buffer solutions The change diagram of the UV-visible absorption spectrum and the variation diagram of the absorption value at the characteristic absorption peak with time.

[0076] figure 1 In (A) compound I-1 (10 -4 mol L -1 ), II-1 (chelerythrine hydrochloride) (10 -4 mol L -1 ) and III-1 (5*10 -5 mol L -1 ) UV-visible absorption spectrum in the buffer solution; (B) compound I-1 (10 -4 mol L -1 ) and III-1 (5*10 -5 mol L -1 ) the UV-Vis absorption spectrum of the mixture in the buffer solution (pH=6.0) changes with the light time; (C) compound I-1 (10 -4 mol L -1...

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Abstract

The invention belongs to the technical field of medical materials, and discloses a method for activating an anti-tumor compound through biological orthogonal photocatalytic oxidative dehydrogenation, a composition and application. The method comprises the following step: carrying out dehydrogenation reaction on dihydrobenzophenanthridine alkaloid under the conditions of illumination and oxygen and under the action of a photocatalyst to obtain the benzophenanthridine alkaloid. The composition is prepared from the dihydrobenzophenanthridine alkaloid and a photocatalyst. The invention also discloses application of the composition in preparation of a cell nucleus targeted light-activated imaging agent and / or a light-activated anti-tumor product. The oxidative dehydrogenation method is simple and efficient; the dihydrobenzophenanthridine alkaloid and the photocatalyst are high in light activation efficiency under the aerobic condition; the fluorescent probe is used in cells, is illuminated under the oxygen condition, can realize nucleus-targeted specific light-activated fluorescence imaging in living cells, and has the advantages of high light activation efficiency, low cytotoxicity and the like. Through illumination control, the composition disclosed by the invention has a relatively good anti-tumor effect.

Description

technical field [0001] The invention belongs to the technical field of medical materials, and in particular relates to a method, composition and application of bio-orthogonal photocatalytic oxidation dehydrogenation to activate anti-tumor compounds. Background technique [0002] Traditional chemotherapy has defects such as poor targeting and large side effects, which limit its application. The method of light-activated chemotherapy can control and activate the anti-cancer activity of drugs by light. However, current photoactivated chemotherapy methods usually require quantitative modification of photoresponsive groups on chemotherapeutic drugs, and the synthesis steps are complex and easily generate toxic byproducts. [0003] For the method of photoactivation, people have also carried out some researches. For example, the Chinese patent application with the application number 201911425786.0 discloses the oxidative dehydrogenation method of compounds with cell nucleus-targe...

Claims

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Application Information

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IPC IPC(8): C07D491/056A61K31/4741A61P35/00
CPCC07D491/056A61P35/00
Inventor 唐本忠高蒙杨鑫
Owner SOUTH CHINA UNIV OF TECH
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