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Nitric oxide and cisplatin co-delivery poly-pre-drug nano-particles as well as preparation and application thereof

A nitric oxide and nanoparticle technology, applied in the field of medical polymers, can solve problems such as toxic side effects, low curative effect, etc., and achieve the effect of improving water solubility

Active Publication Date: 2020-06-09
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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  • Nitric oxide and cisplatin co-delivery poly-pre-drug nano-particles as well as preparation and application thereof
  • Nitric oxide and cisplatin co-delivery poly-pre-drug nano-particles as well as preparation and application thereof
  • Nitric oxide and cisplatin co-delivery poly-pre-drug nano-particles as well as preparation and application thereof

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

[0048] The specific reaction equation is as follows:

[0049]

Embodiment 2

[0050] Example 2. Preparation of Reductive Response Cisplatin Monomer PPM

[0051] Dissolve cisplatin (0.2g, 0.667mmol) in deionized water (5mL), add hydrogen peroxide (7mL6.0mmol) and stir at 70°C for 5h to obtain hydroxylated cisplatin, and then use cold water, ethanol, ether Each was washed 3 times and dried in vacuum (yield 78.6%). Take the above hydroxylated cisplatinum (0.2g, 0.6mmol) dissolved in 2mL N,N-dimethylacetamide, add methacrylic anhydride (0.19g, 1.23mmol), stir overnight at 70°C, add 1mL acetone to get a bright yellow solid , washed with acetone and diethyl ether three times each, 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-(phenylthioformylthio) pentanoic 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 into the ampoule to dissolve. The mixture was degassed and freeze-thawed for three times, then sealed under vacuum, stirred and reacted at 65°C for 24 hours, and then the polymerization reaction was stopped with liquid nitrogen, the reaction bottle was opened, the reaction mixture was dialyzed (1.5KDa), and vacuum freeze-dried 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 nitric oxide and cisplatin co-delivery poly-pre-drug nano-particles as well as preparation and application thereof. Nitric oxide and cisplatin pre-drug monomers are released by utilizing raw materials such as chloro-alpha-methylstyrene and cisplatin; polymerization is carried out at a high-transformation ratio by using a one-step method, so that the polymer P(DMA-co-Pt-co-No) containing two pre-drug repeated units is obtained. In a tumor cell reductive environment, nitryl responds GSH, and NO is released out; and tetravalentplatinum responds GSH and then the cisplatin is released out, and high-concentration GSH in a tumor micro-environment is fully utilized, so that drug release is realized, and a promotion effect of the NO on drugs is developed. By adopting the poly-pre-drug nano-particles, the water solubility and the stability of the drugs are improved, and the poly-pre-drug nano-particles have the controlled release characteristic.

Description

technical field [0001] The invention belongs to the field of medical polymers, and in particular relates to a 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, which is widely involved in and regulates 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 functions. Under abnormal conditions, in order to exert the killing effect of NO and reduce drug resistance, it is necessary to supplement NO exogenously. NO donors are just in response to clinical needs. produced. Nitrates are the most commonly used nitric oxide donor drugs. Compared with S-nitrosothiol and azoeniumdiolkoxide donors, nitrites have better stabi...

Claims

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Application Information

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IPC IPC(8): A61K33/243A61K47/58A61P35/00B82Y5/00B82Y40/00C08F220/54C08F212/14C08F230/04C08F2/38A61K33/00
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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