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Photoresponse-nitric oxide donor molecule and derivatives and preparing method thereof

A nitric oxide and light-responsive technology, which is applied in the field of medicine, can solve the problems of toxicity, N-nitrosamine derivatives' photosensitivity is not ideal, limitations, etc., and achieve the effect of reducing toxicity

Active Publication Date: 2019-05-24
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the photosensitivity of N-nitrosamine derivatives is not ideal at present, and at the same time, it has its own toxicity.
Practical applications of photoresponsive nitric oxide donor molecules in biomedicine are greatly limited

Method used

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  • Photoresponse-nitric oxide donor molecule and derivatives and preparing method thereof
  • Photoresponse-nitric oxide donor molecule and derivatives and preparing method thereof
  • Photoresponse-nitric oxide donor molecule and derivatives and preparing method thereof

Examples

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preparation example Construction

[0071] The present invention also provides a method for preparing a light-responsive nitric oxide donor molecule, comprising:

[0072] Will R 1 CHO, CH 2 (OH)-R 2 -NH 2 React with ethyl methacrylate isocyanate to obtain structure shown in formula (I),

[0073]

[0074] where the R 1 C6-C20 unsubstituted benzyl, C6-C20 substituted benzyl, C5-C20 substituted heteroaryl, C2-C10 alkyl substituted oxyacyl or C5-C10 heteroaryl substituent oxyacyl ;

[0075] The R 2 for-OCH 2 -Ar-(M) a -,

[0076] The Ar is an unsubstituted aryl group of C6-C20, a substituted aryl group of C6-C20 or a heteroaryl group of C4-C15;

[0077] Said M is -OCON(CH 3 )CH 2 -;

[0078] The a is 0 or 1.

[0079] According to the present invention, the present invention will R 1 CHO, CH 2 (OH)-R 2 -NH 2 React with ethyl methacrylate isocyanate to obtain the structure shown in formula (I), wherein, the present invention has no special requirements on the reaction mode, and those skilled in th...

Embodiment 1

[0105] 1-1) Preparation of photoresponsive nitric oxide donor molecule NBNBC (where R1 is o-nitrobenzaldehyde; R2 is 4-aminobenzyl alcohol)

[0106]

[0107] Preparation method: Dissolve 2g (16.24mmol) of 4-aminobenzyl alcohol (self-made) and 2.45g (16.24mmol) of o-nitrobenzaldehyde in 60mL of ethanol, stir at room temperature for 5min, and precipitate appears. The reaction solution was suction filtered to obtain 2 g (7.80 mmol) of filter cake, which was dissolved in 30 mL of tetrahydrofuran, and 0.295 g (7.80 mmol) of NaBH 4 Stir at room temperature for 2h. Add 5 mL of water to the reaction system, spin dry tetrahydrofuran, extract with dichloromethane, and dry with anhydrous sodium sulfate. Next, 1.03 g (3.97 mmol) of the reduced product was dissolved in 20 mL of glacial acetic acid, and 0.30 g (4.41 mmol) of NaNO2 aqueous solution (60 mL), and the reaction was stirred at room temperature for 20 min. Afterwards, the reaction solution was added to saturated aqueous sodiu...

Embodiment 2

[0122] Embodiment 2 Light releases nitric oxide

[0123] Nitric oxide release was quantified with Griess reagent. Use a portable UV lamp (365nm, ~4mW / cm 2 ) irradiate the nano-assembly 1 and assembly 2 obtained in Example 1, respectively. Specifically, take the assembly 1 or assembly 2 that has been illuminated for different times and mix it with an equal volume of Griess reagent, place it in the dark for 10 minutes, and test their UV Absorption spectrum, the content of nitric oxide release was quantified by the absorbance at 526nm.

[0124] see results Figure 5 , Figure 5 Curves for quantitative analysis of nitric oxide release under low-dose light conditions for the vesicles obtained from the self-assembly of polymer BP1 and the vesicles obtained from the self-assembly of polymer BP2; , the amount of nitric oxide released tends to be stable, and the assembly releases 80% of nitric oxide. When assembly 2 is illuminated for 7 hours, the assembly releases 26.8% of NO. The...

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Abstract

The invention provides a photoresponse-nitric oxide donor molecule and derivatives and a preparing method thereof. The photoresponse-nitric oxide donor molecule of the structure shown in the formula (I) can make a sensitive response under the low radiation intensity by selecting a proper structure, a high-molecular prodrug can be further prepared, self-assembling is further conducted, a high-molecular medicine good in performance is obtained, and the toxicity is reduced compared with an existing photoresponse-nitric oxide donor molecule.

Description

technical field [0001] The invention relates to the field of medicines, in particular to photoresponsive nitric oxide donor molecules, derivatives thereof and preparation methods thereof. Background technique [0002] Nitric oxide is recognized as an important gas signaling molecule in the cardiovascular and central nervous systems. In recent years, nitric oxide has important application prospects in the treatment of cancer, inflammation, trauma and so on. For example, in cancer treatment, low concentrations of nitric oxide can significantly reverse the multidrug resistance behavior of cancer cells, while higher concentrations of nitric oxide can directly kill cancer cells. In addition, nitric oxide plays an important role in immune response, inflammation, and pathogen infection. [0003] At present, the donors used to prepare releasable nitric oxide are mainly organic nitrates, diazenediol derivatives (NONOates), and thionitrosothiols. However, organic nitrates can only ...

Claims

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Application Information

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IPC IPC(8): C07C269/02C07C271/16C07D213/76A61K31/704A61K47/58A61P27/02C08F293/00C08F220/36
Inventor 胡进明段宇恬
Owner UNIV OF SCI & TECH OF CHINA
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