CN107693853B - 一种同时具有响应性药物释放和抗菌功能的涂层及其制备方法 - Google Patents

一种同时具有响应性药物释放和抗菌功能的涂层及其制备方法 Download PDF

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CN107693853B
CN107693853B CN201710938788.4A CN201710938788A CN107693853B CN 107693853 B CN107693853 B CN 107693853B CN 201710938788 A CN201710938788 A CN 201710938788A CN 107693853 B CN107693853 B CN 107693853B
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刘晓亚
李杨
朱叶
孟龙
魏玮
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Tianjin Xinjin Hengli Plastic Powder Co.,Ltd.
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Abstract

本发明提供了一种可刺激响应性释药的季铵盐型抗菌涂层的制备方法，所得涂层在具有较好杀菌效果的同时，能实现治疗药物的响应性释放。该涂层材料的制备方法是：通过自由基聚合制备具有氧化还原响应性聚合物聚1‑溴十二烷基甲基丙烯酸二甲氨基乙酯季铵盐‑co‑N‑[2‑(吡啶‑2‑二硫烷基)‑乙基]‑丙烯酰胺‑co‑甲基丙烯酸甲酯(PPDM)，进一步将聚合物与小分子药物溶于有机溶剂中，通过选择性溶剂法制备氧化还原响应性载药胶体粒子，最后以上述载药胶体粒子水分散液为沉积液，通过电泳沉积技术在316L不锈钢表面制备涂层。该涂层不仅对大肠杆菌和金黄色葡萄球菌具有较好的抑制作用，而且还可以通过对还原性物质例谷胱甘肽的响应实现药物的控制释放；同时本发明涂层制备方法具有过程简单、条件可控、适用基材广、药物负载率高等优点。

Description

一种同时具有响应性药物释放和抗菌功能的涂层及其制备 方法
技术领域
本发明涉及一种同时具有响应性药物释放和抗菌功能的涂层及其制备方法，属于抗菌表面、抗菌涂层领域。
技术背景
生物医用金属材料临床应用时易引起细菌粘附、增殖，进一步造成细菌感染，引发炎症、疼痛、发热等一系列并发症。在金属材料表面制备抗菌涂层成为改善上述问题的主要方法，目前，抗菌涂层主要分为两类：接触型和缓释型。接触型抗菌涂层主要通过在涂层中引入季铵盐，其可破坏细菌细胞膜，造成细菌细胞内蛋白质和营养物质流失，导致细菌死亡；(Shady Farah,Oren Aviv,Natalia Laout,et al.Quaternary ammonium poly(diethylaminoethyl methacrylate)possessing antimicrobial activity.Colloidsand Surfaces B:Biointerfaces,2015,128:608-613.)缓释型抗菌涂层主要是通过负载抗菌剂或金属粒子，通过其释放杀死细菌(Changli Zhao,Peng Hou,Jiahua Ni,et al.Ag-Incorporated FHA Coating on Pure Mg:Degradation and in Vitro AntibacterialProperties.ACS Appl.Mater.Interfaces 2016,8:5093-5103.)。但是缓释型抗菌涂层中药物释放不可控，且长期使用易使细菌产生抗药性；同时，患者伤口部位细菌感染后，会出现炎症、发热、疼痛等并发症，需要施加一定量药物进行治疗。因此，制备一种既可以有效杀死细菌，又能对细菌感染并发症有治疗作用的功能性抗菌涂层是一条有效途径。
本发明提供一种可响应性释放药物且具有抗菌功能的涂层及其制备方法，涂层可响应性释放其中药物，同时可通过季铵盐抑制细菌生长。
发明内容
本发明的目的是提供了一种同时具有响应性药物释放和抗菌功能的涂层及其制备方法，旨在得到可抗菌和氧化还原响应性释药的涂层，具有较好杀菌效果的同时，实现治疗药物的刺激响应性释放。它的设计思路是：通过自由基聚合制备氧化还原响应性聚合物PPDM，进一步利用选择性溶剂法制备载药胶体粒子，最后通过电泳沉积技术在医用金属基材表面制备涂层。该涂层可响应GSH，实现药物的控制释放，并对大肠杆菌和金黄色葡萄球菌具有较好的抑制作用。
本发明的技术方案为：
一种同时具有响应性药物释放和抗菌功能的涂层及其制备方法，包括下列步骤：
D1、氧化还原响应性无规共聚物PPDM的制备：分别称取N-[2-(吡啶-2-二硫烷基)-乙基]-丙烯酰胺PDSA、1-溴十二烷基甲基丙烯酸二甲氨基乙酯季铵盐DMAC12、甲基丙烯酸甲酯MMA及引发剂2,2-偶氮二异丁氰AIBN溶于有机溶剂中，室温下搅拌溶解，在氮气氛围中反应；反应完成后将反应液在无水乙醚中反复沉淀三次，真空干燥即可得到无规共聚物；
三种单体PDSA、DMAC12、MMA的投料摩尔比范围为6:4:0～5:3:2，引发剂加入量占单体总摩尔数的1％～2％，反应温度为60℃～80℃，反应时间为12～24h。
D2、载药胶体粒子的制备：将步骤(1)中所制备得到的无规共聚物PPDM和药物分子共同溶解于有机溶剂中，接着向溶液中逐滴滴加超纯水诱导聚合物与药物分子共组装，制备载药胶体粒子；
制备载药胶体粒子所用氧化还原响应性无规共聚物PPDM溶液浓度范围为0.1～40.0mg/mL，所含药物浓度范围为0.1～10.0mg/mL；超纯水加入量与共聚物溶液体积比为1:0.5～1:2，所制备载药胶体粒子粒径范围为130nm～200nm。
D3、同时具有药物响应性释放和抗菌功能的涂层的制备：以步骤(2)中制备得到的载药胶体粒子水分散液为沉积液，医用金属基材为工作电极，铂片为对电极，通过电泳沉积技术制备功能涂层；
电泳沉积过程中，沉积电压范围为5V～20V，沉积时间范围为0.5min～10min。
本发明的有益效果在于：
(1)本发明制备载药胶体粒子过程简单、方便，药物负载效率高。
(2)利用电泳沉积技术在医用金属材料表面制备涂层，操作方便、设备简单、投资低、涂层制备过程可控，基材适用范围广；
(3)最终制备涂层具有较好的氧化还原响应释药性能，在GSH或GSH浓度较低情况下，药物缓慢释放，当GSH浓度较大为10mM时，涂层中二硫键断裂，涂层亲水性增强，药物大量释放，实现药物可控释放；
(4)最终制备涂层具有较好的抗菌性，当细菌接触涂层时，涂层可通过表面的季铵盐杀死细菌，杀菌率在98％以上。
附图说明
图1为氧化还原响应性释药、抗菌涂层的制备及释药、抗菌图：该涂层可通过季铵盐杀死细菌，同时可响应性释放扑热息痛药物，改善发炎部位疼痛、发热症状；
图2为实施例2中氧化还原响应性释药、抗菌涂层的SEM图：从图中可以看出，涂层表面光滑、致密，可避免药物泄露；
图3为实施例3中氧化还原响应释药、抗菌涂层样品释药结果图：从图中可以看出当无GSH或GSH浓度为10μM时，其药物释放量较低，而当GSH浓度为10mM时，药物释放量为前者的三倍，说明涂层具有较好的响应释药性能；
图4为实施例4中氧化还原响应释药、抗菌涂层样品的抗菌测试结果：从图中可以看出，316L不锈钢表面制备涂层后，金黄色葡萄球菌和大肠杆菌数量均大大较少，杀菌率分别为100％和98％，说明本发明涂层具有较好的抗菌性。
具体实施方式
以下结合实施例对本发明作进一步说明，但本发明并不局限于此。
实施例1：
(1)氧化还原响应性无规共聚物的制备:称取0.288g PDSA、0.406g DMAC12及0.0059g 2,2-偶氮二异丁氰，依次加入到圆底烧瓶中，加入15mL N,N-二甲基甲酰胺做溶剂，通氮气30min，在70℃下反应20h，反应液在无水乙醚中反复沉淀三次，真空干燥即可得到氧化还原响应性无规共聚物；
(2)载药胶体粒子的制备：将步骤(1)制备的无规共聚物与小分子药物例扑热息痛溶解在N,N-二甲基甲酰胺中形成40mg/mL溶液，扑热息痛浓度为10mg/mL，向上述溶液中按体积比1:1滴加超纯水，无规聚合物自组装，部分扑热息痛包覆于无规共聚物胶束中，形成氧化还原响应性载药胶束；
(3)同时具有药物释放和抗菌功能的涂层的制备：以10mL步骤(2)制备胶束溶液为电沉积液，316L不锈钢为工作电极，铂片为对电极，在15V沉积电压下沉积3min，制备具有氧化还原响应性释药性能的季铵盐型涂层。
实施例2：
(1)氧化还原响应性无规共聚物的制备:称取0.48g PDSA、0.4872g DMAC12、0.08gMMA及0.0059g 2,2-偶氮二异丁氰，依次加入到圆底烧瓶中，加入20mL N,N-二甲基甲酰胺做溶剂，通氮气30min，在65℃下反应24h，反应液在无水乙醚中反复沉淀三次，真空干燥即可得到氧化还原响应性无规共聚物；
(2)载药胶体粒子的制备：将步骤(1)制备的无规共聚物与小分子药物例扑热息痛溶解在N,N-二甲基甲酰胺中形成40mg/mL溶液，扑热息痛浓度为10mg/mL，向上述溶液中按体积比1:1滴加超纯水，无规聚合物自组装，部分扑热息痛包覆于无规共聚物胶束中，形成氧化还原响应性载药胶束；
(3)同时具有药物释放和抗菌功能的涂层的制备：以10mL步骤(2)制备胶束溶液为电沉积液，316L不锈钢为工作电极，铂片为对电极，在15V沉积电压下沉积3min，制备具有氧化还原响应性释药性能的季铵盐型涂层，涂层形貌图如图2所示。
实施例3：
(1)氧化还原响应性无规共聚物的制备:称取0.48g PDSA、0.4872g DMAC12、0.08gMMA及0.0059g 2,2-偶氮二异丁氰，依次加入到圆底烧瓶中，加入20mL N,N-二甲基甲酰胺做溶剂，通氮气30min，在65℃下反应24h，反应液在无水乙醚中反复沉淀三次，真空干燥即可得到氧化还原响应性无规共聚物；
(2)载药胶体粒子的制备：将步骤(1)制备的无规共聚物与小分子药物例扑热息痛溶解在N,N-二甲基甲酰胺中形成20mg/mL溶液，扑热息痛浓度为5mg/mL，向上述溶液中按体积比1:2滴加超纯水，无规聚合物自组装，部分扑热息痛包覆于无规共聚物胶束中，形成氧化还原响应性载药胶束；
(3)同时具有药物释放和抗菌功能的涂层的制备：以10mL步骤(2)制备胶束溶液为电沉积液，钛合金为工作电极，铂片为对电极，在15V沉积电压下沉积3min，制备具有氧化还原响应性释药性能的季铵盐型涂层，涂层氧化还原响应释药图如图3所示。
实施例4：
(1)氧化还原响应性无规共聚物的制备:称取0.48g PDSA、0.4872gDMAC12、0.08gMMA及0.0059g 2,2-偶氮二异丁氰，依次加入到圆底烧瓶中，加入20mL N,N-二甲基甲酰胺做溶剂，通氮气30min，在70℃下反应24h，反应液在无水乙醚中反复沉淀三次，真空干燥即可得到氧化还原响应性无规共聚物；(2)载药胶体粒子的制备：将步骤(1)制备的无规共聚物与小分子药物例扑热息痛溶解在N,N-二甲基甲酰胺中形成40mg/mL溶液，扑热息痛浓度为10mg/mL，向上述溶液中按体积比1:1滴加超纯水，无规聚合物自组装，部分扑热息痛包覆于无规共聚物胶束中，形成氧化还原响应性载药胶束；
(3)同时具有药物释放和抗菌功能的涂层的制备：以50mL步骤(2)制备胶束溶液为电沉积液，316L不锈钢为工作电极，铂片为对电极，在5V沉积电压下沉积5min，制备具有氧化还原响应性释药性能的季铵盐型涂层，涂层抗菌图如图4所示。
上述实施例用来说明本发明，而不是对本发明进行限制，在本发明的精神和权利要求的保护范围内，对本发明做出的任何修改和改变，都将落入本发明的保护范围。

Claims (1)

1.一种同时具有响应性药物释放和抗菌功能的涂层及其制备方法，其特征在于：包括下列步骤：
D1、氧化还原响应性无规共聚物PPDM的制备：分别称取N-[2-(吡啶-2-二硫烷基)-乙基]-丙烯酰胺PDSA、1-溴十二烷基甲基丙烯酸二甲氨基乙酯季铵盐DMAC12、甲基丙烯酸甲酯MMA及引发剂2,2-偶氮二异丁氰AIBN溶于有机溶剂中，室温下搅拌溶解，在氮气氛围中反应；反应完成后将反应液在无水乙醚中反复沉淀三次，真空干燥即可得到无规共聚物；三种单体PDSA、DMAC12、MMA的投料摩尔比范围为6:4:0～5:3:2，引发剂加入量占单体总摩尔数的1％～2％，反应温度为60℃～80℃，反应时间为12～24h；
D2、载药胶体粒子的制备：将步骤(1)中所制备得到的无规共聚物PPDM和药物分子共同溶解于有机溶剂中，接着向溶液中逐滴滴加超纯水诱导聚合物与药物分子共组装，制备载药胶体粒子；制备载药胶体粒子所用氧化还原响应性无规共聚物PPDM溶液浓度范围为0.1～40.0mg/mL，所含药物浓度范围为0.1～10.0mg/mL；超纯水加入量与共聚物溶液体积比为1:0.5～1:2，所制备载药胶体粒子粒径范围为130nm～200nm。
D3、同时具有药物响应性释放和抗菌功能的涂层的制备：以步骤(2)中制备得到的载药胶体粒子水分散液为沉积液，医用金属基材为工作电极，铂片为对电极，通过电泳沉积技术制备功能涂层；电泳沉积过程中，沉积电压范围为5V～20V，沉积时间范围为0.5min～10min。
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