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A Nitric Oxide and Cisplatin Co-delivery Polyprodrug Nanoparticles and Its Preparation and Application

A technology of nitric oxide and nanoparticles, applied in the field of medical polymers, can solve the problems of low curative effect, toxic and side effects, etc., and achieve the effect of improving drug stability, good stability, and improving anti-tumor efficiency

Active Publication Date: 2022-03-22
SOUTH CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because cisplatin has serious toxic and side effects on normal tissues, especially acute nephrotoxicity and chronic neurotoxicity; at the same time, many tumors have intrinsic drug resistance and acquired drug resistance to cisplatin, resulting in low curative effect

Method used

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  • A Nitric Oxide and Cisplatin Co-delivery Polyprodrug Nanoparticles and Its Preparation and Application
  • A Nitric Oxide and Cisplatin Co-delivery Polyprodrug Nanoparticles and Its Preparation and Application
  • A Nitric Oxide and Cisplatin Co-delivery Polyprodrug Nanoparticles and Its Preparation and Application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Example 1: Preparation of reductive response p-nitromethylstyrene monomer p-CMS-NO

[0047] In a 100 mL round-bottomed flask, weigh silver nitrate (0.934 g, 5.5 mmol), p-chloromethylstyrene (0.6 g, 3.93 mmol) and 10 mL of acetonitrile, and stir overnight at room temperature in the dark under magnetic stirring conditions. The salt was removed by filtration, the solvent was removed by rotary evaporation, then dissolved in ethyl acetate, washed three times each with water and saturated aqueous NaCl solution, the organic phase was collected, dried over anhydrous sodium sulfate, then filtered and concentrated. A yellow liquid product 1 (0.851 g, yield: 55.5%) was obtained.

[0048] The specific reaction equation is as follows:

[0049]

Embodiment 2

[0050] Example 2. Reduction-responsive cisplatin monomer PPM preparation

[0051] First, cisplatin (0.2g, 0.667mmol) was dissolved in deionized water (5mL), hydrogen peroxide (7mL6.0mmol) was added and stirred at 70°C for 5h to obtain hydroxylated cisplatin. Each was washed 3 times and dried under vacuum (78.6% yield). Dissolve the above hydroxylated cisplatin (0.2g, 0.6mmol) in 2mL of N,N-dimethylacetamide, add methacrylic anhydride (0.19g, 1.23mmol), stir at 70°C overnight, add 1mL of acetone to obtain a bright yellow solid , washed three times with acetone and ether, and dried in vacuo to obtain a yellow solid powder (0.22 g, yield: 63.5%).

[0052] The specific reaction equation is as follows:

[0053]

Embodiment 3

[0054] Example 3. Preparation of polymer p(DMA-co-Pt-co-NO) by "one-pot" method

[0055] DMA (70mg, 7.0×10 -4 mol), PPM (49mg, 1.04×10 -4 mol), p-CMS-NO (52mg, 3.0×10 - 4 mol), chain transfer agent 4-cyano-4-(phenylthiocarbonylthio)valeric acid (2.9mg, 1.03×10 -5 mol), azobisisobutyronitrile (1.7mg, 1.03×10 -5 mol), 6 mL of 1,4-dioxane and dimethyl sulfoxide (volume ratio=2:1) ​​were added to the ampoule to dissolve. The mixture was degassed and freeze-thawed for three times, then sealed under vacuum, stirred at 65°C for 24 hours, and then stopped the polymerization reaction with liquid nitrogen, opened the reaction flask, dialyzed the reaction mixture (1.5KDa), and vacuum lyophilized to obtain soil Yellow powder.

[0056] The specific reaction equation is as follows:

[0057]

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Abstract

The invention belongs to the field of medical polymers, and discloses a nitric oxide and cisplatin co-delivery polyprodrug nanoparticle and its preparation and application. The present invention uses raw materials such as p-chloromethylstyrene and cisplatin to prepare and release nitric oxide and cisplatin prodrug monomers, and obtains polymer P( DMA-co-Pt-co-NO). In the reducing environment of tumor cells, nitro group responds to GSH to release NO; tetravalent platinum responds to GSH to release cisplatin, making full use of the high concentration of GSH in the tumor microenvironment to release the drug, and play the role of NO in promoting the drug. Polyprodrug nanoparticles enhance the water solubility, stability and controllable release characteristics of drugs.

Description

technical field [0001] The invention belongs to the field of medical polymers, and particularly relates to a kind of nitric oxide and cisplatin co-delivery polyprodrug nanoparticle and its preparation and application. Background technique [0002] Nitric oxide (NO) is a ubiquitous free radical signaling molecule in cells, widely involved in and regulating various physiological and pathological processes, such as vasodilation, nerve signal transduction, immune response, apoptosis and tumorigenesis and metastasis. Under normal physiological conditions, the body can produce an appropriate level of NO to maintain system function. In abnormal conditions, exogenous NO supplementation is required to exert NO killing effect and reduce drug resistance. produced. Nitrate esters are the most commonly used nitric oxide donor drugs. Compared with S-nitrosothiol and azoene diolide donors, nitrite esters have better stability and are not affected by nitric oxide. Temperature, light and p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K9/51A61K33/243A61K47/58A61P35/00B82Y5/00B82Y40/00C08F220/54C08F212/14C08F230/04C08F2/38A61K33/00
CPCA61K33/243A61K47/58B82Y5/00B82Y40/00A61P35/00A61K33/00C08F220/54C08F2/38C08F2438/03A61K2300/00C08F212/14C08F230/04
Inventor 胡祥龙储诚燕
Owner SOUTH CHINA NORMAL UNIVERSITY
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