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Carbon monoxide donor molecule with fluorescent properties and preparation method and application thereof

A carbon monoxide and donor technology, applied in the direction of organic active ingredients, chemical instruments and methods, medical preparations of non-active ingredients, etc., can solve problems such as poor solubility, toxicity of organic solvents, and limit the application of light-triggered release of carbon monoxide. Biocompatibility, good controllable release effect

Active Publication Date: 2019-11-12
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

3-Hydroxyflavone derivatives have a large conjugated structure, which directly causes their poor solubility in the state of small molecules, and usually need to add organic solvents to aid in dissolution
At present, in the light-responsive carbon monoxide donor molecules, due to the existence of the naphthalene ring structure, it needs to be dissolved in the presence of organic solvents. The toxicity of organic solvents makes it impossible to be directly used in vivo, which greatly limits the light-triggered Application of releasing carbon monoxide in medicine

Method used

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  • Carbon monoxide donor molecule with fluorescent properties and preparation method and application thereof
  • Carbon monoxide donor molecule with fluorescent properties and preparation method and application thereof
  • Carbon monoxide donor molecule with fluorescent properties and preparation method and application thereof

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preparation example Construction

[0028] The present invention also provides a method for preparing a carbon monoxide donor molecule with fluorescent properties, comprising:

[0029] With the compound of formula (II), p-Hydroxybenzaldehyde, R 1 -Br reacts with the compound of formula (III) structure to obtain the compound of formula (I) structure;

[0030]

[0031] where the R 1 C6-C30 arylalkyl containing substituents or C6-C20 alkoxycarbonyl containing substituents;

[0032] R 2 is methyl or hydrogen;

[0033] R 3 is isocyanate or -OCOOH;

[0034] X is oxygen or NH,

[0035] Y is oxygen or sulfur,

[0036] Z is NH or oxygen.

[0037] According to the present invention, the present invention will have the compound of formula (II), p-hydroxybenzaldehyde, R 1 -Br reacts with the compound of the formula (III) structure to obtain the compound of the formula (I) structure; specifically, the steps are as follows: 1) reacting the compound of the formula (II) structure with p-Hydroxybenzaldehyde, after th...

Embodiment 1

[0057] Preparation of a photoresponsive carbon monoxide donor molecule CORM with fluorescent properties (where R is o-nitrobenzyl bromide, X is oxygen, and Y is oxygen)

[0058]

[0059] Preparation method: Weigh 1 (1g, 5.37mmol), add 15mL ethanol to form a suspension, add sodium hydroxide (5.4mL, 5M, 27mmol), stir at room temperature for 30min, p-hydroxymethylbenzaldehyde (748mg, 5.5 mmol) into the reaction flask, stirred at room temperature for 5h, after the reaction was completed, cooled to 0°C, hydrogen peroxide (2.0mL, 30%) was added dropwise into the reaction flask, and stirred overnight; the pH was acidified to 6.5 with 0.5M HCl to form Yellow precipitate, suction filtered, washed with ethanol, and dried to obtain the product, weighed the product (288mg, 1mmol), potassium carbonate (140mg, 1mmol), added 10mL DMF to dissolve for later use, weighed o-nitrobenzyl bromide (258mg, 1.2 mmol) was added to the reaction flask, the mixture was stirred at room temperature for 1...

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Abstract

The invention provides a carbon monoxide donor molecule with fluorescent properties and a preparation method and application thereof. The carbon monoxide donor molecule provided by the invention has structure as shown in a formula (I), can realize the removal of responsive protection elements and release of carbon monoxide in one step under illumination conditions, and is applicable to preparationof a stable high-molecular polymer which can be further used for preparing assembly material with a stable aqueous phase through self-assembling. Compared with conventional carbon monoxide releasingmolecules, the carbon monoxide donor provided by the invention is capable of realizing good controlled release and has good biocompatibility.

Description

technical field [0001] The invention relates to the field of polymer materials, in particular to a carbon monoxide donor molecule with fluorescent properties and its preparation method and application. Background technique [0002] Carbon monoxide is well known as a toxic gas molecule. In recent years, studies have found that carbon monoxide is similar to nitrogen monoxide and hydrogen sulfide, and can also be used as a gas transmitter. In the human body, carbon monoxide is produced by the cleavage of heme oxidase, which has important applications in protecting cells, regulating physiological processes, anti-inflammation and anti-cancer. However, since the binding speed of carbon monoxide and hemoglobin far exceeds that of oxygen and hemoglobin, the uncontrollable direct inhalation of carbon monoxide makes this method impractical, [0003] At present, the donor materials used to prepare and release carbon monoxide mainly include metal coordination compounds (CORM-2 / CORM-3) ...

Claims

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Application Information

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IPC IPC(8): C07D221/08C07D311/92C09K11/06C08G65/333A61K47/34A61K31/473A61K31/352A61P35/00A61P29/00A61P39/00
CPCA61K31/352A61K31/473A61K47/34A61P29/00A61P35/00A61P39/00C07D221/08C07D311/92C08G65/33396C09K11/06C09K2211/1007C09K2211/1029C09K2211/1088
Inventor 胡进明程健
Owner UNIV OF SCI & TECH OF CHINA
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