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Oxazine compounds and their applications

A compound, oxazine technology, applied in the field of synthesis of new oxazine photo/acoustic sensitizers, can solve problems such as unstable composition ratio of the treatment system, short excitation wavelength, slow metabolism, etc.

Active Publication Date: 2021-06-18
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, the photo / acoustic sensitizers used in clinic are mainly represented by porphyrin and phthalocyanine compounds. Although these compounds have achieved great success in tumor treatment, there are still many defects, such as: the composition ratio of the treatment system Unstable, slow metabolism in the body, short maximum excitation wavelength, prone to phototoxic side effects, etc.
These deficiencies have seriously affected the actual effect and clinical application of photodynamic therapy.
For the preparation and application research of photosensitizers, there are already certain guiding ideologies in the world that can play a guiding role, but for the preparation and application research of sound sensitizers, there is no relevant theoretical guidance, but it can be applied to clinical sonosensitizers. few

Method used

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Examples

Experimental program
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Effect test

preparation example Construction

[0046] The preparation method of the compound of general formula F represented by above-mentioned route comprises the steps:

[0047] (1) In the hydrochloric acid acidification system, p-nitrobenzenediazonium chloride and the compound of formula I were reacted at 25-35° C. for 0.5-2 hours according to the molar ratio of 1:1, to prepare the compound of formula II;

[0048]

[0049] (2) The compound of formula F was prepared by reacting the compound of formula II with 8-hydroxyquinoline at a molar ratio of 1:1 in acidic DMF at 135-145° C. for 2-4 hours.

[0050] The photo / acoustic sensitizer based on oxazine of the present invention has the following characteristics:

[0051] (1) It has certain water solubility and good cell membrane permeability;

[0052] (2) It has excellent near-infrared emission characteristics, and has low biological photobleaching, photodamage and phototoxicity when applied to biological imaging, and the generated fluorescent signal can penetrate deep ...

Embodiment 1

[0059] Embodiment 1: preparation compound F-1

[0060]

[0061] (1) Synthesis of intermediate 1-II

[0062] In the hydrochloric acid acidification system, the compound of p-nitrodiazonium chloride and 1-I was reacted at 25-35°C for 0.5-2 hours according to the molar ratio of 1:1. After the reaction was completed, a brick red color was obtained after suction filtration and washing. The compound of formula 1-II was obtained from the solid powder crude product with a yield of 95%.

[0063] (2) Synthesis of compound F-1

[0064] The intermediate 1-II and quinoline prepared by the above reaction (1) were added into a round bottom flask containing DMF, and 1 mL of perchloric acid solution was added dropwise. After the dropwise addition was completed, the system was stirred for 2.5 hours to stop the reaction, separated by silica gel column chromatography, dichloromethane:methanol (v:v)=8:1 elution and purification to obtain the target compound F-1 with metallic luster in dark bl...

Embodiment 2

[0066] Embodiment 2: compound F-1 spectrum test experiment

[0067] Using the compound F-1 synthesized in Example 1, add the F-1-DMSO solution into dichloromethane and mix well. Its spectral properties were tested by UV-Vis spectrophotometer and fluorescence spectrometer. The result is as figure 2 As shown, the F-1 molecule has a maximum absorption of 680nm and a maximum emission of 700nm in dichloromethane.

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Abstract

Oxazine compounds and their applications. The oxazine compound has the structure of general formula F. The oxazine compounds mentioned in the present invention are a kind of photo / acoustodynamically active organic molecules with near-infrared absorption and emission, as well as photosensitivity and sound-sensitivity. The maximum absorption and emission wavelengths of this type of compound are both greater than 660nm, and the triplet conversion rate is high. Under the condition of light or ultrasound, it can generate active oxygen species with high efficiency, and has a good killing effect on cancer cells and cancer tissues. While achieving photo / acoustic dynamic therapy, there is almost no toxic side effect on normal tissues.

Description

technical field [0001] The invention belongs to the field of anticancer drug design, synthesis and application. It specifically involves the synthesis of new oxazine photo / sound sensitizers, their specific recognition of tumors and their new applications in diagnosis and treatment. Background technique [0002] Photodynamic action refers to the participation of photosensitizers, under the action of light, to make organic cells or biomolecules undergo functional or morphological changes, and in severe cases lead to cell damage and necrosis. In the early stage, this action must involve oxygen, so it is also It is called photosensitization-oxidation, which is called photosensitization in chemistry, and photodynamic effect in biology and medicine. The method of treating diseases with photodynamic effect is called photodynamic therapy (photodynamic therapy, PDT). Photodynamic therapy is a new disease treatment method based on the interaction of light, photosensitizers and oxyge...

Claims

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Application Information

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IPC IPC(8): C07D513/16C07D517/16C09K11/06A61P35/00G01N21/64
CPCA61P35/00G01N21/6428C09K11/06C07D513/16C07D517/16C09K2211/1029C09K2211/1092C09K2211/1096C09K2211/1018A61K9/14A61K41/0033A61K41/0057G01N2021/6439
Inventor 樊江莉姚起超李海东边雅娜李明乐王静云彭孝军
Owner DALIAN UNIV OF TECH
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