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Application of linear polythiourea and hyperbranched polythiourea in preparation of anti-tumor medicines and anti-virus or anti-bacterial medicines

An antibacterial drug, polythiourea technology, applied in the direction of antitumor drugs, antibacterial drugs, antiviral agents, etc., can solve the problems of complicated preparation process and strong toxicity of raw materials.

Active Publication Date: 2016-05-18
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the preparation process of this type of linear polythiourea molecules is extremely cumbersome, and the toxicity of the raw materials used is extremely strong, and the mechanism of their action is that their anionic and rigid aromatic-based polymer skeletons adhere to the virus, not because of their own thiourea group

Method used

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  • Application of linear polythiourea and hyperbranched polythiourea in preparation of anti-tumor medicines and anti-virus or anti-bacterial medicines
  • Application of linear polythiourea and hyperbranched polythiourea in preparation of anti-tumor medicines and anti-virus or anti-bacterial medicines
  • Application of linear polythiourea and hyperbranched polythiourea in preparation of anti-tumor medicines and anti-virus or anti-bacterial medicines

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1 utilizes 1,4-dithioisocyanate butane to react with ethylenediamine to prepare a linear thiourea polymer. The reaction formula is as follows:

[0039]

[0040] 1,4-Dithioisocyanate butane (0.69 g, 4 mmol) and ethylenediamine (0.24 g, 4 mmol) were mixed in 2 mL of dichloromethane, and stirred at room temperature for 24 hours. After three times of precipitation with ether, a colorless viscous product was obtained with a yield of 90% and a number average molecular weight of 14500.

[0041] The above obtained dope (0.7g) and PEG550-NH 2 (1 g) was dissolved in 5 mL of dichloromethane. After the reaction solution was stirred overnight at room temperature, it was precipitated three times with ether to obtain a PEGylated linear polymer containing thiourea (1.0 g).

[0042] The pegylated thiourea-containing linear polymer synthesized in Example 1 was used to carry out an in vivo tumor inhibition test on the human colorectal cancer tumor model of nude mice, and a co...

Embodiment 2

[0045] Embodiment 2 utilizes 1,4-dithioisocyanate butane and three-(2-aminoethyl)amine to react to prepare thiourea-containing hyperbranched polymer

[0046] The reaction formula is as follows:

[0047]

[0048] 1,4-Dithioisocyanate butane (0.69 g, 4 mmol) and tris-(2-aminoethyl)amine (0.58 g, 4 mmol) were mixed in 3 mL of dichloromethane, and stirred at room temperature for 24 hours. After three times of precipitation with ether, a colorless viscous product was obtained with a yield of 93% and a number average molecular weight of 4500.

[0049] After PEG550-COOH (2g) was dissolved in 20mL of dichloromethane, carbonyldiimidazole (1g) was added, and after stirring at room temperature for 15min, the above-mentioned viscous material (0.5g) was added. After the reaction solution was stirred overnight at room temperature, it was precipitated with ether three times to obtain a PEGylated thiourea-containing hyperbranched polymer (1.2 g).

[0050] The thiourea-containing hyperbra...

Embodiment 3

[0051] Example 3 The linear thiourea polymer is prepared by reacting thiourea molecules with 2-hydroxyl-1,3-propanediamine. The reaction formula is as follows:

[0052]

[0053] 1.0000g of thiourea, 1.1839g of 1,3-diamino-2-hydroxypropane and 20mg of p-toluenesulfonic acid were dissolved in 5mL of NMP, and reacted overnight at 160°C under the protection of argon. After the product was precipitated with anhydrous ether, a small amount of After washing with ice water, 1.35 g of the final product represented by formula I was obtained with a yield of 76% and a number average molecular weight of 5000-6000.

[0054] 1 H-NMR (400MHz, DMSO): δ (ppm) 7.76 (s, 2H), 5.13 (d, J = 3.1Hz, 1H), 3.89 (d, J = 3.2Hz, 1H), 3.16 (d, J = 11.8Hz, 2H), 2.92 (d, J = 12.0Hz, 2H).

[0055] Taking the polythiourea molecule (abbreviated as L-PTU) prepared in Example 3 as an example, the MTT (3-(4,5-dimethylthiazole-2)-2,5 -diphenyltetrazolium bromide) method to detect the effect of L-PTU on human l...

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Abstract

The invention discloses an application of linear polythiourea in preparation of anti-tumor medicines and anti-virus or anti-bacterial medicines. The linear polythiourea has the structural formula represented as the formula (I), wherein R1 and R2 are independently selected from hydrogen, C1-C10 alkyl groups and aryl groups, or a hetero atom group containing N, O and S. The number-average molecular weight of the linear polythiourea is 50-50000. The invention also discloses an application of hyperbranched polythiourea in preparation of anti-tumor medicines and anti-virus or anti-bacterial medicines. The hyperbranched polythiourea is prepared by dissolving a monomer containing at least two isothiocyanic acid groups or dissolving thiourea with a monomer containing at least two amine groups in an organic solvent, performing a heating condensation polymerization reaction under protection of an inert gas, and purifying a reaction product to prepare the hyperbranched polythiourea.

Description

technical field [0001] The invention belongs to the technical field of polymer applications, and in particular relates to the application of linear polythiourea and hyperbranched polythiourea in the preparation of antitumor drugs and antiviral or antibacterial drugs. Background technique [0002] Polymers are widely used in biomedicine, especially as pharmaceutical excipients in pharmaceuticals, giving drugs certain dosage forms and other functions, but most polymers themselves have no biological activity. Polymerization of biologically active molecules as monomers yields biologically active polymers. For example, Shen Youqing et al. (Tang et al. Curcumin polymers as anticancer conjugates. Biomaterials 31, 7139-49 (2010)) used curcumin, a traditional Chinese medicine ingredient with anti-tumor activity, as one of the monomers to prepare a curcumin polymer with anti-tumor ability. [0003] Thiourea compounds (TUs) refer to a class of compounds with thiourea groups (-NH-CS-NH...

Claims

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Application Information

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IPC IPC(8): A61K31/795A61P35/00A61P31/04A61P31/12
Inventor 申有青邵世群刘祥瑞唐建斌
Owner ZHEJIANG UNIV
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