CN115160655B - 一种兼具抗菌性、粘附性、自愈性和高透明度的水凝胶及其制备方法与应用 - Google Patents
一种兼具抗菌性、粘附性、自愈性和高透明度的水凝胶及其制备方法与应用 Download PDFInfo
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Abstract
本发明公开了提供了一种兼具抗菌性、粘附性、自愈性和高透明度的水凝胶及其制备方法与应用,属于生物材料技术领域。本发明水凝胶包括多巴胺接枝的大分子化合物、巯基和金属镓离子(Ga3+),本发明利用镓离子作为抗菌剂,通过Ga3+与多巴胺形成可逆的金属配位作用构建水凝胶三维网络结构,同时含巯基化合物的‑SH基团能够阻止多巴胺的酚羟基被氧化成醌,既能保留多巴胺的抗氧化性和粘附性,又能保持水凝胶高度透明,在可见光范围内透明度接近100%。这种水凝胶制备方法克服多巴胺与金属离子配位作用构建的水凝胶颜色深、不透明且功能单一的缺点。此外,水凝胶中负载有含巯基的药物,本发明可用于功能敷料、载药水凝胶、传感器等领域。
Description
技术领域
本发明属于水凝胶材料技术领域,特别是涉及一种兼具抗菌性、粘附性、自愈性和高透明度的水凝胶材料及其制备方法与应用。
技术背景
水凝胶由于其独特的三维网状结构,具有优异的亲水性、保水性以及生物相容性。在生物医学、传感器、可穿戴电子设备以及水处理等各领域具有广阔的应用前景,而功能单一的传统水凝胶在应用上受到了限制。
为满足不断进步发展的现代医学的需求,作为医用材料的水凝胶被赋予越来越多的功能性,如:粘附性、自愈合、抗菌性等。目前,文献报道中有许多水凝胶受天然贻贝足丝启发,仿生性地引入多巴胺与多价金属离子配位来提高水凝胶的粘附性和自愈合性能,取得了较好的结果。但是,根据目前研究发现,多巴胺与多价金属离子配位受控于环境的pH范围。当pH>7时,多巴胺才能够与多价金属阳离子形成不同配位程度的配合物,而这种pH范围同时也容易使多巴胺的酚羟基被氧化为醌的结构,不仅导致部分粘附性损失,多巴胺的抗氧化性能受损,还导致水凝胶体系形成不透明的棕褐色甚至黑色,这极大地影响了水凝胶的应用范围。
镓离子(Ga3+)的离子半径、电势能以及电子亲和力等与铁离子极为相似,以至于生物系统无法分别,外源性镓进入细菌后取代蛋白结构中的铁。由于镓离子不具有氧化还原活性。因此,镓离子扰乱铁离子与蛋白质和螯合剂的结合,干扰了细菌的DNA合成和各种氧化还原反应,从而达到杀菌的目的。而水凝胶含有多巴胺与金属镓离子(Ga3+)配位体系时,形成呈棕褐色水凝胶,大大影响了其应用范围。
发明内容
为了解决含有pH响应的多巴胺与镓离子(Ga3+)配位体系水凝胶的颜色及透明度问题。本发明通过掺杂含有强还原性的-SH基团的化合物,制备了一种兼具粘附性、自愈合及抗菌性的透明水凝胶。可用于生物医用材料领域。加入Ga3+溶液与大分子化合物链上多巴胺形成pH响应的金属配位键,具有强还原性-SH基团的化合物能够阻止多巴胺的酚羟基被氧化成醌,既能保留多巴胺的抗氧化性和粘附性,又能保持水凝胶高度透明,从而制得兼具抗菌性、粘附性自愈性和高透明度的水凝胶。
本发明包含以下技术方案:
本发明提供了一种兼具抗菌性、粘附性、自愈性和高透明度的水凝胶,包含:
(a)多巴胺接枝的大分子化合物;
(b)巯基;
(c)金属镓离子(Ga3+);
所述金属镓离子与所述大分子化合物链上的多巴胺形成pH响应的金属配位键。
巯基基团具有极强的还原性,能够阻止多巴胺的酚羟基被氧化成为醌的结构,充分保留多巴胺的粘附特性和抗氧化特性,避免水凝胶体系形成不透明的棕褐色甚至黑色。而提前在多巴胺与多价金属离子配位的水凝胶体系中,加入乙酰半胱氨酸或谷胱甘肽等含有巯基的化合物,可制得在可见光范围内透明度接近100%的透明水凝胶。
作为可选方式,在上述水凝胶中,其制备原料包含:
(a)一类多巴胺接枝的大分子化合物;
(b)一类含有巯基的化合物;
(c)一类能够提供金属镓离子(Ga3+)的化合物。
作为可选方式,在上述水凝胶中,所述大分子化合物为透明质酸、聚谷氨酸、聚天冬氨酸、肝素、硫酸软骨素、明胶、羧甲基壳聚糖中的一种或几种。
作为可选方式,在上述水凝胶中,所述含有巯基的化合物为乙酰半胱氨酸、谷胱甘肽中的一种或几种。
作为可选方式,在上述水凝胶中,所述能够提供金属镓离子(Ga3+)的化合物为氯化镓、硝酸镓中的一种或几种。
作为可选方式,在上述水凝胶中,所述水凝胶中巯基与大分子化合物链上多巴胺基团比为1:1-1:4。
作为可选方式,在上述水凝胶中,所述水凝胶中Ga3+与大分子化合物链上多巴胺基团的比例为1:1-1:3。
作为可选方式,在上述水凝胶中,所述水凝胶pH值在7-10。
作为可选方式,在上述水凝胶中,其结构式如下:
作为可选方式,在上述水凝胶的结构式中,部分或全部透明质酸主链结构单元被替换为聚谷氨酸、聚天冬氨酸、肝素、硫酸软骨素、明胶、羧甲基壳聚糖的主链结构单元中的一种或几种。
本发明还提供了一种上述水凝胶的制备方法,其特征在于,将各制备原料均匀混合并调节pH值。
作为可选方式,在上述制备方法中,包括以下步骤:
(1)获取多巴胺接枝的大分子化合物;
(2)加入含有巯基(-SH)基团的化合物;
(3)加入金属镓离子(Ga3+)溶液;
(4)调节混合体系pH值,并充分涡旋,得到水凝胶。
作为可选方式,在上述制备方法中,将多巴胺共价接枝至大分子化合物主链上生成多巴胺修饰的大分子化合物。
作为可选方式,在上述制备方法中,将多巴胺修饰的大分子化合物溶于去离子水中,得到浓度为0.5%-10%的溶液。
作为可选方式,在上述制备方法中,将含有-SH的小分子药物溶解到多巴胺修饰的大分子化合物溶液中,控制-SH基与大分子化合物链上多巴胺基团比为1:1-1:4。
作为可选方式,在上述制备方法中,将金属盐溶于去离子水后得到金属镓离子(Ga3+)溶液,进一步的,所述溶液中金属镓离子(Ga3+)的浓度为0.1-0.3mol/L。控制Ga3+与大分子化合物链上多巴胺基团的比例为1:1-1:3
作为可选方式,在上述制备方法中,通过NaOH溶液调节混合体系的pH值,进一步的,pH值被调节控制在7-10。
作为可选方式,在上述制备方法中,包括以下步骤:
(1)将多巴胺共价接枝至透明质酸主链上生成多巴胺修饰的大分子化合物;
(2)在溶液(1)中加入含有巯基(-SH)基团的化合物;
(3)将金属镓离子(Ga3+)溶液加入上述混合溶液(2)中,并使用NaOH调节所得混合溶液的pH,充分涡旋,制得兼具抗菌性、粘附性、自愈性和高透明度的水凝胶材料。
本发明还提供了一种上述水凝胶的应用,其特征在于,将其应用于医药、传感器等领域,如用于制备眼部用药、创伤敷料、药物递送系统等。
本说明书中公开的所有特征,或公开的所有方法或过程中的步骤,除了互相排斥的特征和/或步骤以外,均可以以任何方式组合。应当理解,前述构思以及在下面更加详细地描述的额外构思的所有组合只要在这样的构思不相互矛盾的情况下都可以被视为本公开的发明主题的一部分。另外,所要求保护的主题的所有组合都被视为本公开的发明主题的一部分。
本发明的有益效果:
本发明利用镓离子作为抗菌剂,通过Ga3+与多巴胺形成可逆的金属配位作用构建水凝胶三维网络结构,同时含巯基化合物的-SH基团能够阻止多巴胺的酚羟基被氧化成醌,既能保留多巴胺的抗氧化性和粘附性,又能保持水凝胶高度透明,在可见光范围内透明度接近100%。这种水凝胶制备方法克服多巴胺与金属离子配位作用构建的水凝胶颜色深、不透明且功能单一的缺点。此外,水凝胶中负载有含巯基的药物,本发明可用于医药、传感器等领域。
附图说明:
图1是多巴胺修饰的透明质酸核磁氢谱图;
图2是具有黏附性的可自愈透明抗菌水凝胶照片;
图3是具有黏附性的可自愈透明抗菌水凝胶照片;
图4是具有黏附性的可自愈透明抗菌水凝胶透光率表征;
图5是具有黏附性的可自愈透明抗菌水凝胶自愈合照片;
图6是流变仪表征具有黏附性的可自愈透明抗菌水凝胶自愈合性能;
图7水凝胶对抗大肠杆菌的抗菌性能;
图8是对比例1中所述水凝胶的结构式和照片。
具体实施方式:
以下通过实施例的具体实施方式再对本发明的上述内容作进一步的详细说明。但不应当将此理解为本发明上述主题的范围仅限于以下的实例。在不脱离本发明的精神和原则之内做的任何修改,以及根据本领域普通技术知识和惯用手段做出的等同替换或者改进,均应包括在本发明的保护范围内。
实施例1
将0.4033g透明质酸溶解于40mL的去离子水,再将0.1917g的1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐(EDC·HCl)与0.1151g的N-羟基琥珀酰亚胺(NHS)加入,在pH5.5的条件下搅拌活化30min。在室温下,遮光,抽真空,通氮气条件下,加入0.1896g多巴胺反应过夜。用1M HCl调节蒸馏水pH 5.5左右,透析3天除去未反应的多巴胺盐酸盐以及缩合剂等小分子,最后将产品冷冻4h以上,用冻干机冻干后待用。
称取0.2g多巴胺修饰的透明质酸溶于39.8mL去离子水中,取200μL上述溶液加入14μL的0.06M乙酰半胱氨酸,充分涡旋。加入8μL的0.1M硝酸镓溶液,并通过10μL的0.5M氢氧化钠溶液调节pH至7,充分涡旋得到具有黏附性的可自愈透明抗菌水凝胶。结果如图2所示:水凝胶呈显出无色透明状,且从涡旋后的离心管转移出来时具有明显黏附性能。
通过紫外分光光度仪在380-780nm表征水凝胶的透光率。见图4。390-780nm可见波长范围内透光率大于90%的是透明水凝胶;透光率为10-90%的为半透明水凝胶;那些透光率低于10%的为不透明水凝胶。因此,在380-780nm表征水凝胶的透光率表明所制备的水凝胶是高度透明的。
实施例2
将0.4033g透明质酸溶解于40mL的去离子水,再将0.3834g的1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐(EDC·HCl)与0.2302g的N-羟基琥珀酰亚胺(NHS)加入,在pH5.5的条件下搅拌活化30min。在室温下,遮光,抽真空,通氮气条件下,加入0.3792g多巴胺反应过夜。用1M HCl调节蒸馏水pH 5.5左右,透析3天除去未反应的多巴胺盐酸盐以及缩合剂等小分子,最后将产品冷冻4h以上,用冻干机冻干后待用。
称取0.2g多巴胺修饰的透明质酸溶于39.8mL去离子水中,取200μL上述溶液加入4μL的0.06M乙酰半胱氨酸,充分涡旋。加入3μL的0.1M硝酸镓溶液,并通过15μL的0.5M氢氧化钠溶液调节pH至8,充分涡旋得到具有黏附性的可自愈透明抗菌水凝胶。
实施例3
将0.4033g透明质酸溶解于40mL的去离子水,再将0.5751g的1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐(EDC·HCl)与0.3453g的N-羟基琥珀酰亚胺(NHS)加入,在pH5.5的条件下搅拌活化30min。在室温下,遮光,抽真空,通氮气条件下,加入0.5688g多巴胺反应过夜。用1M HCl调节蒸馏水pH 5.5左右,透析3天除去未反应的多巴胺盐酸盐以及缩合剂等小分子,最后将产品冷冻4h以上,用冻干机冻干后待用。通过核磁氢谱表征多巴胺接枝率,结果如图1所示:其中,6.8-7.2ppm为多巴胺邻苯二酚结构苯环上的质子峰,2.0ppm为透明质酸分子链上甲基的质子峰,通过两处质子峰面积积分比计算可得,多巴胺接枝率为47%。
称取0.2g多巴胺修饰的透明质酸溶于1.8mL去离子水中,取200μL上述溶液加入35μL的0.12M乙酰半胱氨酸,充分涡旋。加入19μL的0.3M硝酸镓溶液,并通过20μL的0.5M氢氧化钠溶液调节pH至10,充分涡旋得到具有黏附性的可自愈透明抗菌水凝胶。见图3,水凝胶呈显出无色透明状,且从涡旋后的离心管转移出来时具有明显黏附性能。
通过紫外分光光度仪在380-780nm表征水凝胶的透光率。见图4,390-780nm可见波长范围内透光率大于90%的是透明水凝胶;透光率为10-90%的为半透明水凝胶;那些透光率低于10%的为不透明水凝胶。因此,在380-780nm表征水凝胶的透光率表明所制备的水凝胶是高度透明的。
将水凝胶用罗丹明染色后,将染色水凝胶与无色水凝胶拼接一起5min,通过外力牵拉表征水凝胶自愈合能力。见图5,拼接后愈合后的水凝胶不仅能承受自重,且能承受一定拉力,表明了水凝胶优异的自愈合能力。
将水凝胶置于流变平板,分别施加0%与1000%的应力扫描,检测水凝胶储能模量与损耗模量间的变化关系评估水凝胶自愈合能力。见图6,当对水凝胶施加0%的应力时,水凝胶的储能模量大于损耗模量(G’>G”),水凝胶展现出固体行为;当交变应力施加1000%时,水凝胶的储能模量小于损耗模量(G’<G”),表示水凝胶网络被破坏。60s后,再次对水凝胶施加0%的应力时,水凝胶再次展现出固体行为,表示水凝胶的交联网络已修复。并在接下来4个交变应力周期内,水凝胶重复被破坏并修复,表明水凝胶具有优异的自愈合能力。
将水凝胶置于涂有100μL的大肠杆菌的固体培养基平板中心,共培养24h,观察水凝胶抑菌能力。a,水凝胶周围的固体培养基上出现明显的抑菌区域,表明水凝胶材料具有抗菌能力。
实施例4
将0.4633g硫酸软骨素溶解于46mL的去离子水,再将0.5751g的1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐(EDC·HCl)与0.3453g的N-羟基琥珀酰亚胺(NHS)加入,在pH5.5的条件下搅拌活化30min。在室温下,遮光,抽真空,通氮气条件下,加入0.5688g多巴胺反应过夜。用1M HCl调节蒸馏水pH 5.5左右,透析3天除去未反应的多巴胺盐酸盐以及缩合剂等小分子,最后将产品冷冻4h以上,用冻干机冻干后待用。
称取0.2g多巴胺修饰的硫酸软骨素溶于1.8mL去离子水中,取200μL上述溶液加入35μL的0.12M谷胱甘肽,充分涡旋。加入19μL的0.3M氯化镓溶液,并通过20μL的0.5M氢氧化钠溶液调节pH至10,充分涡旋得到具有黏附性的可自愈透明抗菌水凝胶。所得水凝胶的透明度、自愈性、抗菌性与实施例3相当。
实施例5
将0.1470g聚谷氨酸溶解于15mL的去离子水,再将0.3834g的1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐(EDC·HCl)与0.2302g的N-羟基琥珀酰亚胺(NHS)加入,在pH5.5的条件下搅拌活化30min。在室温下,遮光,抽真空,通氮气条件下,加入0.3792g多巴胺反应过夜。用1M HCl调节蒸馏水pH 5.5左右,透析3天除去未反应的多巴胺盐酸盐以及缩合剂等小分子,最后将产品冷冻4h以上,用冻干机冻干后待用。
称取0.2g多巴胺修饰的聚谷氨酸溶于39.8mL去离子水中,取200μL上述溶液加入4μL的0.06M谷胱甘肽,充分涡旋。加入3μL的0.1M硝酸镓溶液,并通过15μL的0.5M氢氧化钠溶液调节pH至8,充分涡旋得到具有黏附性的可自愈透明抗菌水凝胶。所得水凝胶的透明度、自愈性、抗菌性与实施例3相当。
实施例6
将0.5435g羧甲基壳聚糖溶解于54mL的去离子水,再将0.1917g的1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐(EDC·HCl)与0.1151g的N-羟基琥珀酰亚胺(NHS)加入,在pH5.5的条件下搅拌活化30min。在室温下,遮光,抽真空,通氮气条件下,加入0.1896g多巴胺反应过夜。用1M HCl调节蒸馏水pH 5.5左右,透析3天除去未反应的多巴胺盐酸盐以及缩合剂等小分子,最后将产品冷冻4h以上,用冻干机冻干后待用。
称取0.2g多巴胺修饰的羧甲基壳聚糖溶于39.8mL去离子水中,取200μL上述溶液加入14μL的0.06M乙酰半胱氨酸,充分涡旋。加入8μL的0.1M氯化镓溶液,并通过10μL的0.5M氢氧化钠溶液调节pH至7,充分涡旋得到具有黏附性的可自愈透明抗菌水凝胶。所得水凝胶的透明度、自愈性、抗菌性与实施例3相当。
对比例1:
采用实施例3所述方法制备多巴胺修饰透明质酸(HA-DA),称取0.2g多巴胺修饰的透明质酸溶于1.8mL去离子水中,得到多巴胺修饰透明质酸(HA-DA)溶液,取200μL上述溶液加入19μL的0.3M硝酸铁溶液,并通过20μL的0.5M氢氧化钠溶液调节pH至10,充分涡旋得到水凝胶。
采用实施例3所述方法制备多巴胺修饰透明质酸(HA-DA),称取0.2g多巴胺修饰的透明质酸溶于1.8mL去离子水中,得到多巴胺修饰透明质酸(HA-DA)溶液,取200μL上述溶液加入19μL的0.3M硝酸镓溶液,并通过20μL的0.5M氢氧化钠溶液调节pH至10,充分涡旋得到水凝胶。
结果如图8所示:在铁离子(Fe3+)与多巴胺修饰透明质酸(HA-DA)形成凝胶网络中,其中游离的多巴胺在碱性环境下变为醌结构,且过量游离的Fe3+会使醌的结构增加,制得水凝胶呈黑色不透明;
镓离子(Ga3+)与多巴胺修饰透明质酸形成凝胶网络,其中游离的多巴胺在碱性环境下变为醌结构,制得凝胶呈红棕色,但Ga3+加入改善了水凝胶的透明度,并赋予了水凝胶抗菌性;
当体系中含有半胱氨酸(含有巯基的化合物)时,巯基将氧化的醌结构还原为邻苯二酚结构,制得凝胶无色透明的抗菌水凝胶。
以上所述仅为本发明的优选应用例,对本发明而言仅是说明性的,而非限制性的;本领域普通技术人员理解,在本发明权利要求所限定的精神和范围内可对其进行许多改变,修改,甚至等效变更,但都将落入本发明的保护范围。
Claims (8)
1.一种兼具抗菌性、粘附性、自愈性和高透明度的水凝胶,其特征在于,其制备方法包括以下步骤:
(1)获取多巴胺接枝的大分子化合物;
(2)加入含有巯基基团的化合物与多巴胺反应,阻止多巴胺的酚羟基被氧化成醌;
(3)加入三价金属镓离子溶液;
(4)调节混合体系pH值,并充分涡旋,得到水凝胶;
其中,多巴胺的氨基与大分子化合物主链上的羧基反应;
所述三价金属镓离子与所述大分子化合物链上的多巴胺形成pH响应的金属配位键。
2.根据权利要求1所述的水凝胶,其特征在于,所述大分子化合物为透明质酸、聚谷氨酸、聚天冬氨酸、肝素、硫酸软骨素、明胶、羧甲基壳聚糖中的一种或几种;所述含有巯基的化合物为半胱氨酸、乙酰半胱氨酸、谷胱甘肽中的一种或几种;所述三价金属镓离子溶液为氯化镓、硝酸镓中的一种或几种。
3.根据权利要求1所述的水凝胶,其特征在于,所述水凝胶中巯基与大分子化合物链上多巴胺基团比为1:1-1:4。
4.根据权利要求1所述的水凝胶,其特征在于,所述水凝胶中三价金属镓离子与大分子化合物链上多巴胺基团的比例为1:1-1:3。
5.根据权利要求1所述的水凝胶,其特征在于,所述水凝胶pH值在7-10。
6.权利要求1-5中任意一个所述水凝胶的制备方法,其特征在于,将各制备原料均匀混合并调节pH值。
7.根据权利要求6所述水凝胶的制备方法,其特征在于,将多巴胺共价接枝至大分子化合物主链上生成多巴胺修饰的大分子化合物。
8.一种如权利要求1所述的水凝胶的应用,其特征在于,将其用于制备功能敷料,载药水凝胶或传感器。
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