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Lawsone copolymer with antineoplastic activity and preparation method thereof

An anti-tumor activity and a technology of shamranthine, which is applied in the field of polymer chemistry, can solve the problems of toxic and side reactions, poor water solubility of shamranthine, etc., and achieve the effects of reducing toxicity, good biological water solubility, and promoting inhibitory effect.

Inactive Publication Date: 2014-12-10
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Due to the poor water solubility of hennain, the selection of co-solvents (absolute ethanol, DMSO, etc.) will cause a variety of toxic and side effects

Method used

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  • Lawsone copolymer with antineoplastic activity and preparation method thereof
  • Lawsone copolymer with antineoplastic activity and preparation method thereof
  • Lawsone copolymer with antineoplastic activity and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] (1) Preparation of intermediate compound (a): Weigh 0.5279 g (3 mmol) of 2-hydroxy-1,4-naphthoquinone in a flask, dissolve it in 30 ml of acetone, add 0.4146 g (3 mmol) of Water K 2 CO 3 As an acid-binding agent, under the protection of nitrogen, in an ice-water bath, under constant stirring, slowly drop 0.3763 ​​g (3.6 mmol) of methacryloyl chloride, and react at room temperature. During the reaction, TCL was used to monitor the progress of the reaction. Suction filtration after the reaction was completed, the filtrate was concentrated and the crude product was separated with a silica gel column (ethyl acetate / petroleum ether = 1 / 40 (v / v)), the product components were collected, and the solvent was evaporated to obtain 0.7432 g of a yellow solid. The rate is 88%.

[0046] 1 H NMR (400 MHz, CCl 3 , δ, ppm): 2.111 (s, 3H, -CH 3 ), 5.915 (s, 1H, -C=CH 2 ), 6.455 (s, 1H, -C=CH 2 ), 6.862 (s, 1H, naphthyl ring), 7.809 (d, 2H, naphthyl ring), 8.138 (t, 2H, naphthyl rin...

Embodiment 2

[0050] (1) Preparation of intermediate compound: Same as Example 1.

[0051] (2) Preparation of copolymer: Weigh 0.1589 g (92%, 1.15 mmol) of HPMA into a Shleck bottle, heat to dissolve with 0.5 ml of DMSO, then add 0.5 ml of acetone; weigh 0.0242 g (8%, 0.1 mol) intermediate compound into the Shleck bottle, stir until dissolved, add 0.0145 g (8%, wt) azoisobutyronitrile (AIBN) when cooled to room temperature, vacuumize and nitrogen cycle 3~5 times, seal Finally, keep the temperature at about 55°C and react for 24 hours. Precipitate with a mixture of acetone and ether (volume ratio 7:3), filter and dissolve the precipitate with 1ml of anhydrous methanol, centrifuge with an ultrafiltration concentration centrifuge tube with a molecular weight of 3000, remove small molecules, and obtain 56mg of polymer. The yield is about 38.2%.

[0052] m n =2.4×10 4 ,M w / M n =1.16. 1 H NMR (400 MHz, D 2 O, δ, ppm): 0.785(-CH 3 ), 0.942 (-CH 3 ), 1.521-1.639 (-CH 2 -), 2.854-2.998 (...

Embodiment 3

[0054] (1) Preparation of intermediate compound: Same as Example 1.

[0055] (2) Preparation of copolymer: Weigh 0.2488 g (90%, 1.8 mmol) of HPMA into a Shleck bottle, heat and dissolve with 0.2 ml of DMSO, then add 0.2 ml of acetone; weigh 0.0484 g (10%, 0.2 mol) intermediate compound into the Shleck bottle, stir until dissolved, add 0.0238 g (8%, wt) azoisobutyronitrile (AIBN) when cooled to room temperature, vacuumize and nitrogen cycle 3~5 times, seal Finally, keep the temperature at about 55°C and react for 24 hours. Precipitate with a mixture of acetone and ether (volume ratio 7:3), filter and dissolve the precipitate with 1ml of anhydrous methanol, centrifuge with an ultrafiltration concentration centrifuge tube with a molecular weight of 3000, remove small molecules, and obtain 85mg of polymer. The yield is about 28.6%.

[0056] m n =2.4×10 4 ,M w / M n =1.16. 1 H NMR (400 MHz, D 2 O, δ, ppm): 0.808(-CH 3 ), 1.019 (-CH 3 ), 1.579-1.724 (-CH 2 -), 2.914-3.042 ...

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Abstract

The invention provides a lawsone copolymer with antineoplastic activity, and belongs to the field of macromolecular chemistry and applications. The lawsone copolymer is a macromolecular copolymer with good biological compatibility, and is formed by connecting 2-hydroxy-1,4-naphthaquinone with N-(2-hydroxypropyl) methacrylamide in a polymerization manner. According to the copolymer, the activity of 2-hydroxy-1,4-naphthaquinone is superposed with that of N-(2-hydroxypropyl) methacrylamide, so that an inhibiting effect of the polymer on a tumor is facilitated, the toxicity of the polymer is reduced, and a good biological water solubility is represented. An in-vivo tumor cell growth inhibition experiment proves that the copolymer has a better tumor inhibiting effect on a liver cancer H22 cell, and a new clue is provided for preparing anti-tumor drugs.

Description

technical field [0001] The invention belongs to the field of macromolecular chemistry, and relates to a hennain copolymer with antitumor activity—N-(2-hydroxypropyl)methacrylamide-2-hydroxyl-1,4-naphthoquinone; the invention At the same time, it also relates to a preparation method of the copolymer; the invention also relates to the tumor suppressing effect of the copolymer on liver cancer H22 cells. Background technique [0002] Cancer has become one of the major threats to human health, and it is on the rise. 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. [0003] Naphthoquinones are a class of small molecular compounds that widely exist in nature and have various biological activities. According to th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F220/58C08F220/30A61K47/48A61P35/00
Inventor 袁建超贾宗苗承萍栗静宋凤英袁兵年王福州
Owner NORTHWEST NORMAL UNIVERSITY
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