阅读说明：本技术 一种季铵化含糖超支化聚合物及其制备方法和应用 (Quaternized sugar-containing hyperbranched polymer and preparation method and application thereof ) 是由 朱韵 李果 廖明佳 于 2020-06-09 设计创作，主要内容包括：本发明公开了一种季铵化含糖超支化聚合物,步骤为：1)将1-(2-氨基乙基)哌嗪、聚乙二醇丙烯酸酯和氨基葡萄糖盐酸盐在水中完全溶解,在惰性气体氛围下,加入三乙胺,避光,60℃～70℃下,反应3～5天,在丙酮中沉淀,烘干,得到含糖超支化聚合物,所述的1-(2-氨基乙基)哌嗪和聚乙二醇丙烯酸酯的摩尔比为2:3；2)以理论叔胺量为准,将步骤1)制得的含糖超支化聚合物与溴代十二烷以1：2的摩尔比溶于甲醇和乙醇的混合溶剂中,在50℃～60℃下连续反应7～8天,反应结束后旋干溶剂,常温真空烘干。本发明季铵化含糖超支化聚合物对大肠杆菌的最低抑菌浓度为62.5μg/mL,对大肠杆菌具有靶向选择性。(The invention discloses a quaternized sugar-containing hyperbranched polymer, which comprises the following steps: 1) completely dissolving 1- (2-aminoethyl) piperazine, polyethylene glycol acrylate and glucosamine hydrochloride in water, adding triethylamine in an inert gas atmosphere, keeping out of the sun, reacting for 3-5 days at 60-70 ℃, precipitating in acetone, and drying to obtain a sugar-containing hyperbranched polymer, wherein the molar ratio of the 1- (2-aminoethyl) piperazine to the polyethylene glycol acrylate is 2: 3; 2) based on the theoretical amount of tertiary amine, mixing the sugar-containing hyperbranched polymer prepared in the step 1) with bromododecane in a ratio of 1: 2, dissolving in a mixed solvent of methanol and ethanol, continuously reacting for 7-8 days at 50-60 ℃, spin-drying the solvent after the reaction is finished, and vacuum-drying at normal temperature. The minimum inhibitory concentration of the quaternized sugar-containing hyperbranched polymer on escherichia coli is 62.5 mu g/mL, and the quaternized sugar-containing hyperbranched polymer has targeting selectivity on escherichia coli.)

1. A quaternized sugar-containing hyperbranched polymer is characterized by comprising the following steps:

1) completely dissolving 1- (2-aminoethyl) piperazine, polyethylene glycol acrylate and glucosamine hydrochloride in water, adding triethylamine in an inert gas atmosphere, keeping out of the sun, reacting for 3-5 days at 60-70 ℃, precipitating in acetone, and drying to obtain a sugar-containing hyperbranched polymer, wherein the molar ratio of the 1- (2-aminoethyl) piperazine to the polyethylene glycol acrylate is 2: 3;

2) based on the theoretical amount of tertiary amine, mixing the sugar-containing hyperbranched polymer prepared in the step 1) with bromododecane in a ratio of 1: 2, dissolving in a mixed solvent of methanol and ethanol, continuously reacting for 7-8 days at 50-60 ℃, spin-drying the solvent after the reaction is finished, and vacuum-drying at normal temperature.

2. The method for preparing quaternized sugar-containing hyperbranched polymer according to claim 1, wherein the number of moles of glucosamine hydrochloride in step 1) is greater than 2 times the number of moles of polyethylene glycol acrylate.

3. The quaternized sugar-containing hyperbranched polymer obtained by the method for preparing a quaternized sugar-containing hyperbranched polymer according to claim 1.

4. The use of a quaternized sugar-containing hyperbranched polymer according to claim 3 for the preparation of a bactericide.

5. The use of a quaternized sugar-containing hyperbranched polymer according to claim 4 for the preparation of a bactericide, wherein the bactericide can target Escherichia coli.

Technical Field

The invention belongs to the field of antibacterial materials, and relates to a quaternized sugar-containing hyperbranched polymer, and a preparation method and application thereof.

Background

The quaternized hyperbranched polymer is weakly positively charged, the surface of a bacterial cell membrane is negatively charged, and the quaternized hyperbranched polymer and the bacterial cell membrane can be adsorbed by coulomb force. After the antibacterial agent is adsorbed by bacteria, the antibacterial agent diffuses and penetrates cell walls, and hydrophobic alkyl long chains are combined with phospholipid bilayers on the cell membranes to cause wrinkling and deformation of the cell membranes, and cell contents such as RNA, DNA and K⁺And the leakage is avoided, and finally the purpose of killing bacteria is achieved. Because the quaternized sugar-containing hyperbranched polymer has larger relative molecular mass and higher charge density, the quaternized sugar-containing hyperbranched polymer can better and faster adsorb bacteria, so the quaternized sugar-containing hyperbranched polymer has better antibacterial performance compared with smaller molecular quaternary ammonium salt. FimH lectin at the end of bacterial pili is capable of specifically recognizing sugar molecules, thereby mediating the specific adhesion of bacteria to oligosaccharide-containing receptors on host cells. The monosaccharide or the monosaccharide derivative is modified on the surface of the antibacterial agent, so that the selectivity and the affinity of the antibacterial agent and microorganisms such as bacteria can be improved, the local concentration of the antibacterial agent on the surface of the bacteria is increased, and the aim of reducing the dosage of the antibacterial agent is fulfilled. Each monosaccharide in the sugar-containing hyperbranched polymer is a side group of a main chain and is in a free state when combined with FimH. According to the carbohydrate cluster effect, the carbohydrate-containing hyperbranched polymer has stronger specific recognition and binding capacity to bacteria than monosaccharide molecules. In conclusion, the quaternized sugar-containing hyperbranched polymer has obvious advantages in antibacterial property and targeting property, and is expected to become a low-dose and high-efficiency antibacterial high polymer material.

Disclosure of Invention

In view of the above, the present invention aims to provide a quaternized sugar-containing hyperbranched polymer, and a preparation method and an application thereof.

In order to achieve the purpose, the invention provides the following technical scheme:

1. a quaternized sugar-containing hyperbranched polymer comprises the following steps:

1) completely dissolving 1- (2-aminoethyl) piperazine, polyethylene glycol acrylate and glucosamine hydrochloride in water, adding triethylamine in an inert gas atmosphere, keeping out of the sun, reacting for 3-5 days at 60-70 ℃, precipitating in acetone, and drying to obtain a sugar-containing hyperbranched polymer, wherein the molar ratio of the 1- (2-aminoethyl) piperazine to the polyethylene glycol acrylate is 2: 3;

2) based on the theoretical amount of tertiary amine, mixing the sugar-containing hyperbranched polymer prepared in the step 1) with bromododecane in a ratio of 1: 2, dissolving in a mixed solvent of methanol and ethanol, continuously reacting for 7-8 days at 50-60 ℃, spin-drying the solvent after the reaction is finished, and vacuum-drying at normal temperature.

Further, the mole number of the glucosamine hydrochloride in the step 1) is more than 2 times of that of the polyethylene glycol acrylate.

2. The quaternized sugar-containing hyperbranched polymer is prepared by the preparation method of the quaternized sugar-containing hyperbranched polymer.

3. The quaternized sugar-containing hyperbranched polymer is applied to preparation of bactericides.

Further, the bactericide can target escherichia coli.

The invention has the beneficial effects that: according to the invention, a sugar-containing hyperbranched polymer is synthesized through one-pot reaction of three monomers, namely polyethylene glycol acrylate, 1- (2-aminoethyl) piperazine and glucosamine, quaternization is carried out continuously, the quaternized sugar-containing hyperbranched polymer can be identified and adhered to escherichia coli in a targeted manner through glucose on the surface, and bacteria are killed through the electropositivity of quaternary ammonium salt. The invention determines that the minimum inhibitory concentration of the quaternized sugar-containing hyperbranched polymer to escherichia coli is 62.5 mu g/mL by a dilution coating plate method, and the quaternized sugar-containing hyperbranched polymer has a good antibacterial effect. Confocal microscopy images of escherichia coli demonstrate the targeting selectivity of the quaternized sugar-containing hyperbranched polymer. The quaternized sugar-containing hyperbranched polymer can be identified and adhered to escherichia coli in a targeted manner through glucose on the surface, and has targeted selectivity on the escherichia coli.

Drawings

In order to make the object, technical scheme and beneficial effect of the invention more clear, the invention provides the following drawings for explanation:

FIG. 1 is a synthetic route for quaternized sugar-containing hyperbranched polymers.

FIG. 2 is a graph of the experiment of measuring the minimum inhibitory concentration by a dilution coating plate method.

FIG. 3 is a graph showing the relationship between the antibacterial rate and the concentration of the antibacterial solution.

FIG. 4 is a confocal image of a quaternized sugar-containing hyperbranched polymer co-cultured with Escherichia coli.

Detailed Description

Preferred embodiments of the present invention will be described in detail below with reference to the accompanying drawings.