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5-fluorouracil copolymer with anti-tumor activity and preparation method of 5-fluorouracil copolymer

A technology of pentafluorouracil and anti-tumor activity, which is applied in the direction of anti-tumor drugs, medical preparations of non-active ingredients, drug combinations, etc., and can solve the problems of poor water solubility of pentafluorouracil, so as to prolong the residence time, promote inhibition and reduce damage Effect

Inactive Publication Date: 2013-04-03
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the poor water solubility of pentafluorouracil, the selection of co-solvents (absolute ethanol, DMSO, etc.) will cause a variety of toxic and side effects

Method used

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  • 5-fluorouracil copolymer with anti-tumor activity and preparation method of 5-fluorouracil copolymer
  • 5-fluorouracil copolymer with anti-tumor activity and preparation method of 5-fluorouracil copolymer
  • 5-fluorouracil copolymer with anti-tumor activity and preparation method of 5-fluorouracil copolymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] (1) Preparation of pentafluorouracil monomer (a): Weigh 0.18 g (1.2 mmol) of pentafluorouracil and dissolve it in 2ml of DMSO, slowly add 0.12 g (1 mmol) of methacryloyl chloride dropwise at room temperature; After reacting for 24 hours, 0.30 g of anhydrous sodium carbonate was added, and after stirring for 6 hours, the sodium carbonate was removed by filtration, and the filtrate was precipitated with ethyl acetate to obtain a white solid, which was washed with acetone, filtered with suction, and dried in vacuum at 25°C for 12 hours to obtain a single Compound (a) 0.15 g, yield 60%.

[0055] 1 H NMR (400MHz, DMSO): δ 7.41 (s, 1H, Cycle-H), 5.86 (s, 1H, C=C-H), 5.48 (s, 1H, C=C-H), 1.65 (s, 3H, CH 3 ). 13 C NMR (400MHz, D 2 O): δ 171.8, 160.6, 151.7, 141.9, 139.7, 126.9, 110.0, 17.5.

[0056] (2) Preparation of pentafluorouracil polymer: First, dissolve 0.10 g (0.5 mmol, 20%) of monomeric compound (a) and 0.28 g (2 mmol, 80%) of HPMA in 1 ml of DMSO in a Shleck react...

Embodiment 2

[0059] (1) Preparation of pentafluorouracil monomer (a): same as Example 1.

[0060] (2) Preparation of pentafluorouracil polymer: First, dissolve 0.0396 g (0.2 mmol, 10%) of monomeric compound (a) and 0.2488 g (1.8 mmol, 90%) of HPMA in 1 ml of DMSO in a Shleck reaction flask , and then add 0.028 g (10%, wt) of azobisisobutyronitrile (AIBN). At this time, vacuumize and fill with nitrogen for 3 to 5 cycles. After sealing, keep the temperature at about 60°C and react for 24 hours. Precipitate the reaction solution with 10 ml of acetone to obtain a light yellow solid. After filtration, dissolve the precipitate with 1 ml of anhydrous methanol, and centrifuge with an ultrafiltration concentration centrifuge tube with a molecular weight of 3000 to remove small molecules. The liquid after centrifugation was dried to obtain a light yellow solid, which was 0.1106 g of the polymer expressed by the structural formula (1), and the yield was 38.7%.

[0061] Mn=1.49×10 4 , Mw / Mn=1.52. 1...

Embodiment 3

[0063] (1) Preparation of pentafluorouracil monomer (a): same as Example 1.

[0064] (2) Preparation of pentafluorouracil polymer: First, dissolve 0.0793 g (0.4 mmol, 15%) of monomeric compound (a) and 0.3123 g (2.26 mmol, 85%) of HPMA in 1 ml of DMSO in a Shleck reaction flask , and then add 0.039 g (10%, wt) of azobisisobutyronitrile (AIBN). At this time, vacuumize and fill with nitrogen for 3 to 5 cycles. After sealing, keep the temperature at about 60°C and react for 24 hours. Precipitate the reaction solution with 10 ml of acetone to obtain a light yellow solid. After filtration, dissolve the precipitate with 1 ml of anhydrous methanol, and centrifuge with an ultrafiltration concentration centrifuge tube with a molecular weight of 3000 to remove small molecules. The liquid after centrifugation was dried to obtain a light yellow solid, which was 0.1643 g of the polymer expressed by the structural formula (1), and the yield was 40.9%.

[0065] Mn=1.32×10 4 , Mw / Mn=1.41. ...

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PUM

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Abstract

The invention provides a 5-fluorouracil copolymer with anti-tumor activity. 5-fluorouracil or 5-fluorouracil and sulfadiazine is or are connected to N-(2-hydroxypropyl) methacrylamide through a polymerization mode to form a macromolecule copolymer with good biological compatibility. The macromolecule copolymer is used for connecting the 5-fluorouracil with anti-tumor activity and the sulfadiazine to a tumor targeted drug carrier N-(2-hydroxypropyl) methacrylamide to ensure that the anti-tumor activity is overlapped, further the inhibition of the macromolecule polymer to tumors is promoted, and the standing time of anti-tumor drugs in tumors is greatly prolonged; and meanwhile, by adopting the macromolecule carrier HPMA (hydroxypropyl methacrylate), the toxicity of the anti-cancer drugs is reduced, the hurt to normal tissues is decreased, and a new idea is provided for preparing novel anti-tumor drugs.

Description

technical field [0001] The present invention relates to two novel polymer copolymers with antitumor activity (one of which also has tumor tendency), N-(2-hydroxypropyl)methacrylamide-pentafluorouracil copolymer and N-(2- The preparation method of hydroxypropyl) methacrylamide-pentafluorouracil-sulfadiazine copolymer, and their application and prospect in the preparation of antitumor drugs. Background technique [0002] Cancer has become one of the main threats to human health, and it is showing an obvious upward trend. Due to the lack of specific drugs to prevent and treat cancer or tumors, cancer has increasingly become the number one cause of human death. The main methods of treating cancer today include radiotherapy, chemotherapy, surgical therapy and gene therapy. Among them, radiotherapy and chemotherapy are extremely important non-surgical treatments, but while killing tumor cells, radiotherapy and chemotherapy also cause serious damage to normal cells in the body. E...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F220/58C08F220/60A61K47/48A61P35/00
Inventor 袁建超苗承萍贾宗栗静宋凤英袁兵年王福州
Owner NORTHWEST NORMAL UNIVERSITY
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