CN113788871A - 一种配位化合物及其制备方法和应用 - Google Patents
一种配位化合物及其制备方法和应用 Download PDFInfo
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- CN113788871A CN113788871A CN202110956537.5A CN202110956537A CN113788871A CN 113788871 A CN113788871 A CN 113788871A CN 202110956537 A CN202110956537 A CN 202110956537A CN 113788871 A CN113788871 A CN 113788871A
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- Prior art keywords
- anthocyanin
- compound
- coordination compound
- wound
- dressing
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Abstract
本发明属医用材料技术领域，公开了一种配位化合物及其制备方法和应用，该配位化合物的原料组分包括花青素和金属离子，花青素具有很强的抗氧化能力和良好的抗菌性能，且花青素结构中的酚羟基能够与金属离子发生螯合作用，也能在温和的条件下与生物组织表面的氨基、巯基、羟基或羧基等发生化学反应生成共价键，化学锚定创面皮肤组织，通过形成共价键提供强粘附力，从而实现在湿态下用于伤口粘合和组织修复，即采用金属‑多酚本机聚合原理，制得花青素‑金属离子配位化合物。本发明还利用静电纺丝技术制备支架材料，通过负载花青素‑金属离子配位化合物，制得了一种可原位监测细菌感染和治疗的多功能静电纺丝纤维敷料，应用前景广泛。
Description
技术领域
本发明属于医用材料技术领域，具体涉及一种配位化合物及其制备方法和应用。
背景技术
皮肤是人体的天然屏障，可以保护机体内部组织和器官免受外界的侵袭，同时能感觉和调节体温。当皮肤受到一些不可避免的物理性、化学性及生物性的侵害如烧烫伤、手术创伤、战争创伤、细菌感染足溃疡等会造成皮肤创伤，而皮肤创面一旦形成，人体失去第一道天然保护屏障，细菌等病原微生物便会在创面定植、繁殖和浸润，往往会造成创面感染。由于创面感染常常导致创面延期愈合，严重的创面感染可能会引起机体免疫功能紊乱、全身性感染、脓毒症、败血症，或引发慢性炎症，严重的甚至可导致截肢并危及生命，给患者带来巨大的痛苦及沉重的医疗负担。
有研究表明，创面受到细菌感染时，由于细菌的大量繁殖会产生乳酸，进而导致感染创面的局部酸化(通常pH＜6.5)。且在皮肤受到创伤后，长期的细菌感染导致的慢性炎症会使创面微环境ROS(活性氧reactive oxygen species)水平升高，对创面微环境的细胞和组织造成氧化应激损伤，使创面变得脆弱。并且，过量的ROS会导致内源性干细胞、内皮细胞和巨噬细胞等相关细胞的功能紊乱，抑制血管生成，阻碍创面组织愈合。但目前的创面敷料覆盖在创面以后，无法直观地看到创面的愈合情况，且抗菌性能有限，因此无法满足实际需求。
发明内容
本发明旨在至少解决上述现有技术中存在的技术问题之一。为此，本发明提出一种配位化合物及其制备方法，所述配位化合物能够通过将细菌感染的酸性微环境pH值变化转化为颜色信号，从而实现对创面的感染状态监控并进行实时治疗。
为了克服上述技术问题，本发明采用的技术方案如下：
本发明的第一方面是为了提供一种配位化合物。
具体地，该配位化合物包括花青素结构(配体)和金属离子(中心原子)。
具体地，花青素(Anthocyan,An)，属于天然植物多酚的一种，其结构式为
其中，R1、R2是H、OH或OCH3，R3是H或糖基，R4是OH或糖基。花青素具有很强的抗氧化能力和良好的抗菌性能。花青素类物质的颜色会随pH值变化而变化，pH＜7时呈红色，pH＝7-8时呈紫色，pH>11时呈蓝色，响应机理如下式所示：
通过多酚和金属离子螯合的原理，花青素可与多种金属离子配位形成金属-多酚网络，可作为“分子交联剂”并与合成高分子,(如聚乙二醇(PEG)、聚乙烯醇(PVA)等)形成分子间氢键、亲疏水作用和π-π堆叠等非共价键相互作用力,诱导形成凝胶或者聚集体。其结构中的酚羟基不仅能够与金属离子发生螯合作用(即该配位化合物中的金属离子与酚羟基之间形成配位键)，也能够在温和的条件下与生物组织表面的氨基、巯基、羟基或羧基等发生化学反应生成共价键，化学锚定创面皮肤组织。通过形成共价键提供强粘附力，可以在湿态下用于伤口粘合和组织修复。与此同时，金属离子为创面组织修复提供了重要的抗菌保障。
作为上述方案的进一步改进，制备所述配位化合物的原料组分包括花青素和金属离子化合物；优选地，按重量份计，制备所述化合物的原料组分包括花青素10-30份和金属离子化合物1-30份，水40-89份。
作为上述方案的进一步改进，所述金属离子包括Cu2+、Zn2+、Ag+、Fe3+、Fe2+或稀土金属离子中的至少一种。具体地，锌离子(Zn2+)、铜离子(Cu2+)、银离子(Ag+)、铁离子(Fe3+)、亚铁离子(Fe2+)是本发明所述配位化合物的重要抗菌活性成份，在抗菌和组织修复起了重要的作用，为创面组织修复提供了重要的抗菌保障。
作为上述方案的进一步改进，制备所述配位化合物的原料组分还包括碱性溶液和/或溶剂；优选地，按重量份计，所述碱性溶液为0.1-10份，所述溶剂为90-99.9份。
进一步优选地，所述溶剂包括六氟异丙醇、N,N-二甲基甲酰胺、二甲基亚砜、四氢呋喃、1，4-二氧六环、冰乙酸或蒸馏水中的至少一种。
本发明的第二方面是为了提供一种配位化合物的制备方法。
具体地，该制备方法包括如下步骤：取花青素溶液、金属离子化合物和碱性溶液，使得在碱性条件下混合反应，即得所述配位化合物。具体地，优选为弱碱性条件下进行混合反应。
作为上述方案的进一步改进，还包括分离和提纯；优选地，所述分离和提纯过程为：将所述配位化合物离心、水洗、干燥，得到所述的配位化合物，即为花青素-金属离子配位化合物。
本发明的第三方面是为了提供一种纤维敷料。具体地，该纤维敷料是采用本发明任一项所述的配位化合物制得。
具体地，本发明的纤维敷料为静电纺丝纳米纤维结构，类似细胞外基质(Extracellular matrix，ECM)，其独特的结构可以作为细胞支架为细胞提供粘附和增殖所需要的微环境。因此，本发明中经静电纺丝处理所得的纳米纤维可以为创面愈合提供有利的条件和适宜的创伤微环境，在创面敷料领域应用广泛；同时，其纳米纤维作为创面敷料，可有效阻挡细菌侵入、止血、吸收伤口渗出的组织液、利于气体交换，促进愈合等功能。
作为上述方案的进一步改进，制备所述配位化合物的原料组分还包括高分子化合物；优选地，按重量份计，所述高分子化合物为50-97.9份；
作为上述方案的进一步改进，所述高分子化合物为合成高分子化合物和/或天然高分子化合物；
进一步优选地，所述合成高分子化合物包括聚乳酸和聚己内酯的至少一种；
进一步优选地，所述天然高分子化合物包括明胶、胶原、丝素蛋白和壳聚糖中的至少一种。
本发明的第四方面是为了提供一种纤维敷料的制备方法。具体地，该制备方法包括以步骤：取各原料组分，经混合，得到混合纺丝液；将混合纺丝液进行静电纺丝，得到所述的纤维敷料。
具体地，取所述花青素-金属离子配位化合物和所述高分子化合物分别溶于溶剂中，再经混合，得到混合纺丝液；将混合纺丝液进行静电纺丝，得到所述的纤维敷料。
进一步具体地，在使用时，将多功能纤维敷料覆盖细菌感染创面后，医生和患者可通过手机“拍拍照”“扫一扫”的方式采集敷料图像信息，通过特定软件Q4(颜色识别器)型号提取和分析敷料图像的RGB(RGB表示颜色的参数)数据，即可感知创面pH值变化，实时监控创面感染状态并进行实时治疗。具体地，“颜色识别器”可以是一款版本8.101的名称为“颜色识别器”的手机APP软件。
进一步地，本发明还可以对创面结合光热治疗的方式，以促进伤口的愈合。
本发明的第五方面是为了提供上述配位化合物的应用。
具体为，本发明任一项所述的配位化合物在制备治疗皮肤创伤的药物中的应用。
相对于现有技术，本发明的有益效果如下：
本发明提供了一种配位化合物及其制备方法和应用，该配位化合物的原料组分包括花青素和金属离子，花青素具有很强的抗氧化能力和良好的抗菌性能，其中，花青素结构中的酚羟基能够与金属离子发生螯合作用，也能够在温和的条件下与生物组织表面的氨基、巯基、羟基或羧基等发生化学反应生成共价键，化学锚定创面皮肤组织，通过形成共价键提供强粘附力，从而实现在湿态下用于伤口粘合和组织修复。
本发明采用多酚和金属离子螯合的原理，制得了花青素-金属离子(An-M)配位化合物。
本发明还利用静电纺丝技术制备支架材料，通过负载花青素-金属离子(An-M)配位化合物，制得了一种可原位监测细菌感染和治疗的多功能静电纺丝纤维敷料。
本发明中纤维敷料的制备方法简单，反应条件温和，成本低廉。制备的多功能纤维敷料可将细菌感染的酸性微环境pH值变化转化为颜色信号，为细菌感染创面的原位监测和实时治疗提供了极具临床应用价值的简单、高效、安全的策略，具有相当大的社会效益。
本发明所述的配位化合物可应用在作为制备皮肤创伤的药物中，应用前景广泛。
附图说明
图1为实施例1中所得花青素-金属离子配位化合物的微观形貌图；
图2为本发明的多功能纤维敷料的pH可视化响应性结果；
图3为本发明的多功能纤维敷料的扫描电镜图；
图4是对本发明的实施例3和对比例1分别所得的敷料成品和纯的静电纺丝纤维进行抗菌性能检测所得的抑菌动力学曲线。
具体实施方式
为了让本领域技术人员更加清楚明白本发明所述技术方案，现列举以下实施例进行说明。需要指出的是，以下实施例对本发明要求的保护范围不构成限制作用。
以下实施例中所用的原料、试剂或装置如无特殊说明，均可从常规商业途径得到，或者可以通过现有已知方法得到。
实施例1
花青素-金属离子配位化合物的制备：将0.5g的花青素和0.5g的氯化锌(ZnCl2)溶液分别溶于30mL和10mL去离子水中；室温搅拌一段时间至花青素完全溶解后，将0.1mL氨水(28wt％)滴加到花青素溶液中；继续搅拌5min，将ZnCl2溶液缓慢滴加到碱性花青素溶液中，此时会立即产生大量沉淀；继续搅拌10min，然后5000rpm离心10min，接着用去离子水清洗，重复3次；将离心得到产物冷冻干燥，得到花青素-锌离子配位化合物，其微观形貌的扫描电镜图如图1所示。
多功能静电纺丝纤维敷料的制备：取聚乳酸和明胶溶于六氟异丙醇溶剂中，另取花青素-锌离子配位化合物加入六氟异丙醇溶剂中，超声分散5min，得到聚合物乳液，然后将花青素-锌离子配位化合物溶液加入到聚合物乳液中，得到纺丝溶液。实验采用静电纺丝机，将制备的纺丝溶液加入到20mL注射器中，实验采用23号针头，电压为18kV，接收距离为15cm，纺丝液流速为1mL/h，纺丝温度为25℃，湿度为50％，最后将制得的纺丝纤维置于40℃真空干燥箱中干燥24h，制得多功能纤维敷料实施例成品1。
实施例2
实施例2与实施例1的区别在于，实施例2中采用氯化铜(CuCl2)替换实施例1中的氯化锌(ZnCl2)，其它制备过程与实施例1相同。制得多功能纤维敷料实施例成品2。
实施例3
实施例3与实施例1的区别在于，实施例3中采用硝酸银(AgNO3)替换实施例1中的氯化锌(ZnCl2)，其它制备过程与实施例1相同。制得多功能纤维敷料实施例成品3。
实施例4
实施例4与实施例1的区别在于，实施例4中采用聚氨酯和丝素蛋白替换实施例1中的聚乳酸和明胶，其它制备过程与实施例1相同。制得多功能纤维敷料实施例成品4。
对比例1
对比例1即为未添加本发明中花青素-金属离子配位化合物的纯的静电纺丝纤维，记为纯纤维。
产品性能检测1：
构建细菌感染大鼠创面模型，将实施例1-4分别所得的多功能纤维敷料实施例成品1-4用于创面的细菌感染监测和愈合治疗中发现：
当pH＜7时，敷料的颜色为红色，且随着pH值的降低，红色加深。通常急性感染创面pH＜7，且pH值随创面感染程度加深而降低,从而可以得知急性创面感染程度；
当pH≈7时，敷料的颜色为紫色，通常正常未感染创面pH值维持在近中性,从而可以得知创面没有被感染；
当pH＞7时，敷料的颜色为蓝紫色，通常慢性感染伤创面pH＞7，且pH值随创面感染程度加深而升高。从而可以得知慢性创面感染程度。
发明人通过实验发现，实施例1-4分别所得的多功能纤维敷料实施例成品1-4的均可实现上述创面可视化检测，由于创面的pH值发生变化，进而敷料的颜色发生变化，从而实现实时监控创面感染状态。
这主要是因为静电纺丝纤维负载的花青素-金属离子配位化合物具有pH可视化颜色响应，本发明的多功能纤维敷料分别的pH可视化响应性结果如图2所示，细菌感染造成的酸性创面微环境可加速花青素-锌离子配位化合物的解离和静电纺丝纤维的降解，从而可释放出具有抗氧化功能的花青素和抗菌性能的金属离子，与创面直接接触，实现创面伤口的有效抗菌和治疗。
本发明的多功能纤维敷料实施例成品1-4的扫描电镜图如图3所示，其中，A为多功能纤维敷料实施例成品1的扫描电镜图，B为多功能纤维敷料实施例成品2的扫描电镜图，C为多功能纤维敷料实施例成品3的扫描电镜图，D为多功能纤维敷料实施例成品4的扫描电镜图。从图3中能够看出纯的纺丝纤维表面光滑，纤维直径均匀。随着花青素-金属离子配位化合物(如图3中的箭头所示)的负载，纤维表面变得粗糙，纤维直径变大，且随着负载量的增加，纤维表面粗糙度增加(如图3中的箭头所示，凸起部分增多)。
产品性能检测2：
将本发明的实施例3所得的敷料成品和对比例1的纯的静电纺丝纤维分别用于抗菌检测试验，检测过程大致为：使用无菌吸管吸取一定量的LB液体培养基加入到E.coli冻干粉中(S.aureus使用TSB液体培养基)，然后在37℃恒温培养箱中培养24h后，使用无菌接种环蘸取菌液在LB固体琼脂培养基上划线分区，继续培养12h。E.coli(ATCC 25922)和S.aureus(ATCC 29213)购自于广东省微生物菌种保藏中心；
其中，LB液体培养基是一种培养细菌的常用液体培养基，配方为：胰蛋白胨(Tryptone)10g/L、酵母提取物(Yeast extract)5g/L和氯化钠(NaCl)5g/L。
通过抑菌曲线，探究敷料随时间变化对细菌的抑制效果，首先将S.aureus和E.coli培养至对数期状态，通过离心去除培养基，然后重悬于PBS中，调节细菌浓度为1×104CFU/mL。在无菌玻璃管中加入5mL液体培养基和80μL细菌悬液，然后分别加入等质量(20mg)的纤维敷料，置于37℃恒温摇床中孵育，每隔一段时间后取一定量培养液使用紫外分光光度计测定600nm处的吸光度，得到并根据OD值(optical density光密度的缩写，表示被检测物吸收掉的光密度)绘制抑菌动力学曲线，得到图4，即图4是对本发明的实施例3所得的敷料成品(左图中记为“负载花青素-锌离子复合纤维”)和对比例1的纯的静电纺丝纤维(左图中记为“纯纤维”)进行抗菌性能检测所得的抑菌动力学曲线，其中，左图为对实施例3所得敷料成品(右图中记为“负载花青素-锌离子复合纤维”)与对比例1的纯静电纺丝纤维(右图中记为“纯纤维”)进行抗菌性能检测所得的抑菌动力学曲线，其中的细菌为大肠杆菌；右图为对实施例3所得敷料成品与对比例1的纯静电纺丝纤维进行抗菌性能检测所得的抑菌动力学曲线，其中的细菌为金黄色葡萄球菌。
对于本发明所属技术领域的普通技术人员来说，在不脱离本发明构思的前提下还可以做出若干简单推演或替换，而不必经过创造性的劳动。因此，本领域技术人员根据本发明的揭示，对本发明做出的简单改进都应该在本发明的保护范围之内。上述实施例为本发明的优选实施例，凡与本发明类似的工艺及所作的等效变化，均应属于本发明的保护范畴。
Claims (10)
1.一种配位化合物，其特征在于，包括花青素结构和金属离子。
2.根据权利要求1所述的配位化合物，其特征在于，制备所述配位化合物的原料组分包括花青素和金属离子化合物。
3.根据权利要求1所述的配位化合物，其特征在于，所述金属离子包括Cu2+、Zn2+、Ag+、Fe3+、Fe2+或稀土金属离子中的至少一种。
4.根据权利要求1或2所述的配位化合物，其特征在于，制备所述配位化合物的原料组分还包括碱性溶液和/或溶剂；优选地，按重量份计，所述碱性溶液为0.1-10份，所述溶剂为10-10000份；优选地，所述溶剂包括六氟异丙醇、N,N-二甲基甲酰胺、二甲基亚砜、四氢呋喃、1，4-二氧六环、冰乙酸或蒸馏水中的至少一种。
5.权利要求1至4任一项所述的配位化合物的制备方法，其特征在于，包括如下步骤：取花青素、金属离子化合物，在碱性条件下混合反应，即得所述配位化合物。
6.根据权利要求5所述的制备方法，其特征在于，还包括分离和提纯；优选地，所述分离和提纯过程为：将所述配位化合物离心、水洗、干燥。
7.一种纤维敷料，其特征在于，是采用权利要求1-4任一项所述的配位化合物制得的。
8.根据权利要求7所述的纤维敷料，其特征在于，制备所述纤维敷料的原料组分还包括高分子化合物；优选地，按重量份计，所述高分子化合物为50-97.9份；优选地，所述高分子化合物为合成高分子化合物和/或天然高分子化合物；优选地，所述合成高分子化合物包括聚乳酸和聚己内酯的至少一种；优选地，所述天然高分子化合物包括明胶、胶原、丝素蛋白和壳聚糖中的至少一种。
9.权利要求7或8所述的纤维敷料的制备方法，其特征在于，包括以步骤：取各原料组分，经混合，得到混合纺丝液；将混合纺丝液进行静电纺丝，得到所述的纤维敷料。
10.权利要求1至4任一项所述的配位化合物在制备皮肤创伤药物中的应用。
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