CN116675879A - 一种可注射的抗菌、导电水凝胶 - Google Patents
一种可注射的抗菌、导电水凝胶 Download PDFInfo
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Abstract
本发明为一种可注射的抗菌、导电水凝胶。该水凝胶组成包括聚合物和PBS溶液；其中，聚合物占水凝胶的质量比为5～20wt％，PBS溶液占水凝胶的质量比为95～80wt％；制备中，通过自由基共聚的方式，制备具有醛基和酰肼聚合物的，利用醛基和酰肼基团在室温下可快速反应生成希夫碱键的方法，来实现两性离子、N‑卤胺水凝胶的可注射的性能。本发明得到的水凝胶除了具有水凝胶所具备的良好的生物相容性之外还具有抗菌、导电和防污功能。所述的聚合物的结构式如下：
Description
技术领域
本发明属于高分子技术领域，主要涉及一种可注射的抗菌、导电水凝胶。
背景技术
水凝胶是一种由亲水性聚合物组成的具有三维网状结构的高保水性聚合物材料，具有吸水性、柔韧性、良好的生物相容性以及能够保持伤口周围环境湿润的特点，广泛应用于组织工程、生物医学工程、伤口敷料和电子皮肤等领域。两性离子水凝胶除了具备以上优点之外还有阻止蛋白质非特异性吸附的能力，单纯的阻止蛋白质的非特异性粘附无法完全解决生物污染问题，受伤口部位形状多变的影响即成式水凝胶的应用日益受限，且伤口部位恢复情况复杂急需一种可将伤口部位变化情况转变为电信号的水凝胶来及时检测伤口部位变化。因此，新一代的水凝胶除具有防污的能力还应具有可注射、抗菌、导电的性能。
近年来，希夫碱键因反应条件温和，反应迅速且副产物为水被广泛的应用到可注射水凝胶中。Yoyujing等人(You,Y.；Xie,Y.；Jiang,Z.,Injectable and biocompatiblechitosan-alginic acid hydrogels.Biomedical Materials 2019,14(2),025010.)通过高碘酸处理海藻酸得到二醛海藻酸，壳聚糖的胺基和海藻酸的醛基通过席夫碱反应原位形成水凝胶，该水凝胶具有良好的生物相容性。Caojinying(Cao,J,Y.；Xiao,L.；Injectabledrug-loaded polysaccharide hybrid hydrogels for hemostasis.RSC Advances 2019,9,36858-36866)利用羧甲基壳聚糖(CMC)、明胶(GEL)和氧化藻酸盐(OSA)形成席夫碱键，研制了一种新型可注射黏附载药水凝胶。然而，抗生素的存在可能会使细菌产生耐药性，急需开发出一种固有抗菌性能的水凝胶，但仅具备抗菌性能水凝胶功能单一无法满足复杂现实环境的需求。现开发出一种具有可注射、防污、导电的多功能抗菌水凝胶，来应对复杂的外界环境。
发明内容
本发明的目的在于针对目前水凝胶功能单一的问题，提出一种可注射的抗菌、防污、导电水凝胶。该凝胶组成由两性离子、N-卤胺和希夫碱键组成的可注射水凝胶；制备中，通过自由基共聚的方式，制备具有醛基和酰肼聚合物的，利用醛基和酰肼基团在室温下可快速反应生成希夫碱键的方法，来实现两性离子、N-卤胺水凝胶的可注射的性能本发明得到的水凝胶除了具有水凝胶所具备的良好的生物相容性之外还具有抗菌、导电和防污功能。
本发明解决其技术问题所采用的技术方案是：
一种可注射的抗菌、导电水凝胶，该水凝胶组成包括聚合物和PBS溶液；其中，聚合物占水凝胶的质量比为5～20wt％，PBS溶液占水凝胶的质量比为95～80wt％；
所述的PBS溶液的浓度0.01-0.05M；
所述的聚合物的结构式如下：
结构式中的波折线代表重复的基本单元。
所述的可注射的抗菌、导电水凝胶的制备方法，包括如下步骤：
将聚合物A和聚合物B分别溶解在PBS溶液中，各自得到2.5～10wt％的聚合物溶液，然后将两种聚合物溶液混合，然后所述的水凝胶；
质量比为：聚合物A：聚合物B＝1：1；所述的PBS溶液得浓度为0.01-0.05M；
所述的聚合物A的结构式为：n＝6-8；m＝0.5-2；q＝1-3；
所述的聚合物B的结构式为：n＝3-5；m＝0.5-2；
所述的聚合物A的制备方法，包括如下步骤：
将两性离子、缩醛、N-卤胺加入到蒸馏水中，通入氮气30～60分钟，加入引发剂AIBA，在65～75℃下反应20～30小时，得到的中间体A；将中间体A加入到NaClO溶液中反应1-3h，再透析1～3天得到中间体B溶液，向中间体B溶液中加入浓盐酸，反应8-14h，所得反应液在室温下透析2～3天，冷冻干燥后，得到聚合物A；
其中，每30mL蒸馏水加入1～5g两性离子、0.5～1g缩醛、0.2～0.8gN-卤胺、10～50mg AIBA、10～30mLNaClO溶液、1～3mL浓盐酸；摩尔比为，N-卤胺：NaClO＝1:2；
所述的聚合物B的制备方法，包括如下步骤：
将两性离子、丙稀酸加入到蒸馏水中，通入氮气30-60分钟，加入引发剂AIBA，再在在65～75℃下反应20～30小时，然后向其中加入ADH和EDC，反应8-14小时，其间调节体系pH值保持为4.7～4.8；然后所得反应液在室温下透析2～3天，冷冻干燥后，得到聚合物B；
其中，每30mL蒸馏水加入1～5g两性离子、0.2～1g丙烯酸、20～60mg引发剂；摩尔比为ADH：丙烯酸＝2：1；EDC：丙烯酸＝2：1；
所述的NaClO溶液为1～10wt％；浓盐酸的浓度为6～12M
所述的两性离子为[2-(甲基丙烯酰基氧基)乙基]二甲基-(3-磺酸丙基)氢氧化铵；缩醛为N-(2,2-二甲氧基乙基)丙烯酰胺；N-卤胺为5,5-二甲基-3-(4-乙烯基苄基)咪唑烷-2,4-二酮；ADH为己二酸二酰肼；EDC为1-乙基-(3-二甲基氨基丙基)碳酰二亚胺；
所述的引发剂为偶氮二异丁脒盐酸盐。
本发明的实质性特点为：
本发明的制备方法为两性离子、N-卤胺、缩醛在混合溶剂中70℃时自由基聚合生成三元无规共聚物，生成的聚合物在酸性溶液中室温下反应过夜缩醛生成醛基，把生成的聚合物透析三天冷冻干燥并用PBS溶液配成质量比为10％的溶液以备后续使用；两性离子、N-卤胺、丙烯酸在去离子水中70℃时反应24小时生成三元无规共聚物，在生成的三元无规共聚物溶液中加入ADH/EDC并调节pH为4.75羧酸基变为酰肼基，把生成的聚合物放在蒸馏水中透析三天后冷冻干燥并用PBS溶液配成质量比为10％的溶液以备后续使用。将上述得到的聚合物溶液通过双筒注射器注射即可得到水凝胶
本发明的有益效果为：
1，本发明通过向水凝胶中引入希夫碱键赋予水凝胶可注射的优点，在室温下水凝胶的凝胶时间可达2.90±0.51s左右；
2，两性离子已经被证明为具有优良的生物相容性物质，两性离子的引入可以赋予水凝胶良好的生物相容性，本发明中采用水凝胶的前聚体溶液与L929细胞共培养一天和三天后细胞的存活率都在85％以上，除此之外两性离子还可以利用其可以和水分子结合生成致密的水合层为水凝胶提供优异的防污性能，我们将不同浓度BSA蛋白溶液与水凝胶共培养那个在两性离子含量为80％时可以阻止1000μg/mL蛋白溶液粘附；
3，N-卤胺已经被多人证明具有优异的抗菌效果本发明制备的水凝胶在与大肠杆菌和金黄色葡萄球菌共培养1h后可有效杀死细菌90％以上；
4，因两性离子中同时带有正负电荷且溶解水凝胶前聚体的溶液为PBS溶液可以为水凝胶提供自由移动的离子这就赋予水凝胶导电的性能，经电化学工作站检测后电导率最高可达0.29S/m。
附图说明
图1水凝胶示意图；其中-CH＝N代表希夫碱键；为静电作用；半透明部分代表水凝胶中溶胀的水；
图2为实施例6、7、8、9中水凝胶的扫描电子显微镜图；其中，图2a为PSBMA/AD0；图2b为PSBMA/AD10；图2c为PSBMA/AD20；图2d为PSBMA/AD30；
图3为实施例6、7、8、9中水凝胶防污性能测试图，其中，图3(a)是水凝胶对不同浓度的BSA蛋白的防污性能；图3(b)水凝胶PSBMA/AD0和PSBMA/AD30对大肠杆菌和金黄色葡萄球菌的防污性能
图4为实施例6、7、8、9中水凝胶抗菌性能图，其中，图4(a)为水凝胶对金黄色葡萄球菌图4(b)为大肠杆菌的抗菌性能。
具体实施方式
本发明得到的水凝胶的示意图如图1所示，黑色线条构成了水凝胶中聚合物链段结构，-CH＝N和正负电荷间的静电作用构成了聚合物链段之间的相互作用力，外围的水分子是水凝胶中溶胀的水，整体构成了水凝胶的结构以及组成。
实施例1：
聚合物A10的制备
4g 3-((2-甲基丙烯酰氧基)乙基)二甲基氨)丙烷-1-磺酸酯(两性离子)、0.7093g缩醛、0.4987g N-卤胺用30mL蒸馏水溶解倒入250mL的烧瓶中，通氮气40分钟，加入40mg引发剂AIBA后保氮，在70℃反应24小时，再将含有聚合物的反应液转入到20mL质量比5wt％的NaClO溶液中反应2h，在蒸馏水中用MD3500的透析袋透析两天，将透析得到的产物聚合物溶液全部倒入烧杯中，再向烧杯中加入2mL浓度为12mol/L的HCI溶液，所得聚合物在室温下透析3天，-20℃冷冻干燥后即为目标产物聚合物；其中两性离子：N-卤胺：缩醛的摩尔比为7：1：2。即可得到聚合物A10。
通过细胞计数试剂盒CCK-8对L929细胞进行细胞计数检测，评估具有不同浓度(1μg/ml、0.1μg/ml和0.01μg/ml)的两性离子聚合物前体的细胞相容性。在孵育24h和72h后，所有前体聚合物的细胞活力均保持在85％以上，表明ADMH的存在在不同浓度聚合物下均不会引入任何额外的毒性。由上述实验结果我们可以得出水凝胶具有良好的生物相容性和出色的防污特性，意味着可以在生物材料例如：伤口敷料上，有很大的应用潜力。
实施例2：
聚合物A20的制备
4g两性离子(同实施例1，以下实施例同)、0.8257g缩醛、1.1712gN-卤胺用30mL蒸馏水溶解倒入250mL的烧瓶中，通氮气40分钟，加入40mg引发剂AIBA后保氮，在70℃反应24小时。再将含有聚合物的反应液转入到20mL质量比5wt％的NaClO溶液中反应2h，在蒸馏水中用MD3500的透析袋透析两天，将透析得到的产物聚合物溶液全部倒入烧杯中，再向烧杯中加入2mL浓度为12mol/L的HCl溶液，所得聚合物在室温下透析3天，-20℃冷冻干燥后即为目标产物聚合物；其中两性离子：N-卤胺：缩醛的摩尔比为6：2：2。即可得到聚合物A20。
实施例3：
聚合物的制备A30
4g两性离子、0.9861g缩醛、2.0974gN-卤胺用30mL蒸馏水溶解倒入250mL的烧瓶中，通氮气40分钟，加入40mg引发剂AIBA后保氮，在70℃反应24小时。再将含有聚合物的反应液转入到20mL质量比5wt％的NaClO溶液中反应2h，在蒸馏水中用MD3500的透析袋透析两天，将透析得到的产物聚合物溶液全部倒入烧杯中，再向烧杯中加入2mL浓度为12mol/L的HCl溶液，所得聚合物在室温下透析3天，-20℃冷冻干燥后即为目标产物聚合物；其中两性离子：N-卤胺：缩醛的摩尔比为5：3：2。即可得到聚合物A30。
从实施例1-3中我们可以得到三种具有不同比例N-卤胺的聚合物
实施例4：
聚合物B的制备
4g两性离子、0.2580g丙烯酸(0.0036mol)用30mL蒸馏水溶解倒入250ml的烧瓶中，通氮气40分钟，加入40mg引发剂AIBA后保氮，在70℃反应24小时。取出聚合物溶液在室温下加入1.5678g的ADH(0.0072mol)和1.7253g的EDC(0.0072mol)反应12小时(实现羧酸基转化为酰肼基)，(其间用1mol/L的盐酸调节体系pH，保持始终为4.75)。所得聚合物在室温下透析3天，冻干备用；得到的聚合物PSBMA/H的合成路线如下图所示，其中两性离子：己二酰己二肼＝4：1。
实施例5：
聚合物A0的制备
4g两性离子、0.6183g缩醛溶解在30mL去离子水中倒入250mL烧瓶中，在烧瓶中通入氮气40分钟，加入引发剂AIBA保氮，在70℃的油浴锅中反应24h。再将含有聚合物的反应液转入到20mL质量比5wt％的NaClO溶液中反应2h，在蒸馏水中用MD3500的透析袋透析两天，将透析得到的产物聚合物溶液全部倒入烧杯中，再向烧杯中加入2mL浓度为12mol/L的HCI溶液，所得聚合物在室温下透析3天，-20℃冷冻干燥后即为目标产物聚合物；其中两性离子：缩醛的摩尔比为8：2。即可得到聚合物A0。
实施例6：
水凝胶PSBMA/AD0的制备
第一步，采用实施例4和5得到聚合物B和聚合物A0；
第二步，将实施例4、5制备得到的水凝胶前聚体聚合物分别溶解在PBS溶液中，制备成质量比为各为10wt％的的聚合物PSBMA/H溶液和聚合物PSBMA/A溶液，将两种聚合物溶液等体积混合，3秒钟左右得到的聚合物溶液通过混合成胶。
水凝胶PSBMA/AD0的扫描电子显微镜图像结果如图(1)所示，可以看到水凝胶有明显的三维孔径结构。以BSA蛋白为模型蛋白表征了水凝胶对蛋白质的防污性能如图(3)所示，对于水凝胶PSBMA/AD0即使与高浓度(1000μg/mL)蛋白质溶液一起共培养，也能排斥～100％添加的BSA。以大肠杆菌和金黄色葡萄球菌为细菌模型表征了水凝胶对细菌的防污性能如图(3)所示,大肠杆菌和金黄色葡萄球菌的去除率均超过99％。用电化学工作站测量水凝胶的电阻并通过公式计算水凝胶的电导率如图所示，其中PSBMA/AD0的电导率为0.11S/m。
实施例7
水凝胶PSBMA/AD10的制备
第一步，采用实施例1和4制备得到的聚合物B和A10；
第二步，将实施例1、4制备得到的水凝胶前聚体聚合物均溶解在PBS溶液中，制备成质量比为10wt％的聚合物溶液，实施例4和5制备得到的聚合物溶液通过混合成胶。
水凝胶PSBMA/AD0的扫描电子显微镜图像结果如图(1)所示，可以看到水凝胶有明显的三位孔径结构。以BSA蛋白为模型蛋白表征了水凝胶对蛋白质的防污性能如图所示(3)，当蛋白质浓度≤250μg/mL水凝胶能排斥～100％添加的BSA。用电化学工作站测量水凝胶的电阻并通过公式计算水凝胶的电导率如图所示，其中PSBMA/AD10的电导率为0.10S/m。以大肠杆菌和金黄色葡萄球菌为例测试水凝胶的抗菌性能结果如图(4)所示，当与细菌共培养1h后对大肠杆菌和金黄色葡萄球菌的杀菌率仅为～35％。
实施例8
水凝胶PSBMA/AD20的制备
第一步，采用实施例2和4制备得到的聚合物B和A20；
第二步，将实施例2、4制备得到的水凝胶前聚体聚合物均溶解在PBS溶液中，制备成质量比为10wt％的聚合物溶液，实施例4和5制备得到的聚合物溶液通过混合成胶。
水凝胶PSBMA/AD0的扫描电子显微镜图像结果如图(1)所示，可以看到水凝胶有明显的三位孔径结构。以BSA蛋白为模型蛋白表征了水凝胶对蛋白质的防污性能如图(3)所示，当蛋白质浓度≤250μg/mL水凝胶能排斥～100％添加的BSA，当BSA蛋白质的浓度达到500μg/mL，水凝胶对蛋白质的排斥率为13.4％，蛋白质浓度为1000μg/mL时排斥率为17％。用电化学工作站测量水凝胶的电阻并通过公式计算水凝胶的电导率如图所示，其中PSBMA/AD20的电导率为0.09S/m。以大肠杆菌和金黄色葡萄球菌为例测试水凝胶的抗菌性能结果如图(4)所示，当与细菌共培养1h后对大肠杆菌和金黄色葡萄球菌的杀菌率为～90％。
实施例9
水凝胶PSBMA/AD30的制备
第一步，采用实施例3和4制备得到的聚合物B和A30；
第二步，将实施例3、4制备得到的水凝胶前聚体聚合物均溶解在PBS溶液中，制备成质量比为10wt％的聚合物溶液，实施例4和5制备得到的聚合物溶液通过混合成胶。
水凝胶PSBMA/AD0的扫描电子显微镜图像结果如图(1)所示，可以看到水凝胶有明显的三位孔径结构。以BSA蛋白为模型蛋白表征了水凝胶对蛋白质的防污性能如图(3)所示，当蛋白质浓度≤250μg/mL水凝胶能排斥～100％添加的BSA，当BSA蛋白质的浓度达到500μg/mL，水凝胶对蛋白质的排斥率为21％，蛋白质浓度为1000μg/mL时排斥率为30.7％。用电化学工作站测量水凝胶的电阻并通过公式计算水凝胶的电导率如图所示，其中PSBMA/AD20的电导率为0.08S/m。以大肠杆菌和金黄色葡萄球菌为例测试水凝胶的抗菌性能结果如图(4)所示，当与细菌共培养1h后对大肠杆菌和金黄色葡萄球菌的杀菌率为～90％。
通过实施例7-9，我们可以看到，随着N-卤胺含量的增加，本发明的水溶胶的抗菌性能得到了很大提高，说明本发明具备抗菌性能。
本发明未尽事宜为公知技术。
Claims (5)
1.一种可注射的抗菌、导电水凝胶，其特征为该水凝胶组成包括聚合物和PBS溶液；其中，聚合物占水凝胶的质量比为5～20wt％，PBS溶液占水凝胶的质量比为95～80wt％；
所述的聚合物的结构式如下：
2.如权利要求1所述的可注射的抗菌、导电水凝胶，其特征为所述的PBS溶液的浓度0.01-0.05M。
3.如权利要求1所述的可注射的抗菌、导电水凝胶的制备方法，其特征为该方法包括如下步骤：
将聚合物A和聚合物B分别溶解在PBS溶液中，各自得到2.5～10wt％的聚合物溶液，然后将两种聚合物溶液混合，然后所述的水凝胶；
质量比为：聚合物A：聚合物B＝1：1；所述的PBS溶液得浓度为0.01-0.05M；
所述的聚合物A的结构式为：n＝6-8；m＝0.5-2；q＝1-3；
所述的聚合物B的结构式为：n＝3-5；m＝0.5-2。
4.如权利要求3所述的可注射的抗菌、导电水凝胶的制备方法，其特征为
所述的聚合物A的制备方法，包括如下步骤：
将两性离子、缩醛、N-卤胺加入到蒸馏水中，通入氮气30～60分钟，加入引发剂AIBA，在65～75℃下反应20～30小时，得到的中间体A；将中间体A加入到NaClO溶液中反应1-3h，再透析1～3天得到中间体B溶液，向中间体B溶液中加入浓盐酸，反应8-14h，所得反应液在室温下透析2～3天，冷冻干燥后，得到聚合物A；
其中，每30mL蒸馏水加入1～5g两性离子、0.5～1g缩醛、0.2～0.8gN-卤胺、10～50mgAIBA、10～30mLNaClO溶液、1～3mL浓盐酸；摩尔比为，N-卤胺：NaClO＝1:2；
所述的聚合物B的制备方法，包括如下步骤：
将两性离子、丙稀酸加入到蒸馏水中，通入氮气30-60分钟，加入引发剂AIBA，再在在65～75℃下反应20～30小时，然后向其中加入ADH和EDC，反应8-14小时，其间调节体系pH值保持为4.7～4.8；然后所得反应液在室温下透析2～3天，冷冻干燥后，得到聚合物B；
其中，每30mL蒸馏水加入1～5g两性离子、0.2～1g丙烯酸、20～60mg引发剂；摩尔比为ADH：丙烯酸＝2：1；EDC：丙烯酸＝2：1；
所述的两性离子为[2-(甲基丙烯酰基氧基)乙基]二甲基-(3-磺酸丙基)氢氧化铵；缩醛为N-(2,2-二甲氧基乙基)丙烯酰胺；N-卤胺为5,5-二甲基-3-(4-乙烯基苄基)咪唑烷-2,4-二酮。
5.如权利要求3所述的可注射的抗菌、导电水凝胶的制备方法，其特征为所述的NaCIO溶液为1～10wt％；浓盐酸的浓度为6～12M。
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