CN116210897A - 一种ros响应型虾青素抗炎水凝胶及其制备方法与应用 - Google Patents
一种ros响应型虾青素抗炎水凝胶及其制备方法与应用 Download PDFInfo
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Abstract
本发明公开了一种ROS响应型虾青素抗炎水凝胶及其制备方法与应用，属于水凝胶技术领域，包括以下步骤：(1)海藻酸钠苯硼酸的合成；(2)Alg/PBA‑Asta‑C22:6的合成；(3)ROS响应型虾青素抗炎水凝胶的制备。本发明以化学改性的方式，合成了具有新型ROS响应型虾青素抗炎水凝胶(Alg/PBA‑Asta‑C22:6水凝胶)，其生物适应性强、稳定性好，合成步骤简单，且初步验证该ROS响应型虾青素抗炎水凝胶具有体外ROS响应效果及生物抗炎性能。
Description
技术领域
本发明涉及水凝胶技术领域，特别是涉及一种ROS响应型虾青素抗炎水凝胶及其制备方法与应用。
背景技术
虾青素(Astaxanthin，Asta)是一种类胡萝卜素，在自然界以游离虾青素(Freeastaxanthin，F-Asta)和虾青素衍生物(Astaxanthin ester，Asta-E)两种形式存在。虾青素分子中具有的β-紫罗兰酮环和多不饱和共轭双键会导致虾青素分子价电子的偏移，大量淬灭活性氧(Reactive oxygen species，ROS)，由此赋予虾青素强抗氧化性，因此，虾青素是一种出色的活性氧清除剂。然而，在食品加工和存储过程中，虾青素的高效能应用仍是亟待解决的难题。
生物体内炎症或癌症部位往往蓄积大量ROS而导致氧化应激并产生一系列的细胞和组织损伤，加重炎性反应，刺激生物体促炎细胞因子的产生，从而加重炎症的症状。而虾青素可以有效地抑制炎症，但由于其水溶性及稳定性差，导致生物利用度低而抑制了其功能发挥。
因此，Asta-C22:6作为高效能虾青素酯被期待在体内表现更好的抗炎活性，如何构建高效递送系统(如特异响应性递送材料及高效能虾青素酯)以提高虾青素在体内的抗炎功能是本领域技术人员亟需解决的技术问题。
发明内容
本发明的目的是提供新型ROS响应型抗炎水凝胶及其制备方法与应用。苯硼酸(PBA)易被过氧化氢氧化使碳硼键断裂，因此，本发明设想苯硼酸可作为ROS响应性触发基团，构建具有ROS响应性的虾青素体系，以解决上述现有技术存在的问题。
为实现上述目的，本发明提供了如下方案：
一种ROS响应型虾青素抗炎水凝胶的制备方法，包括以下步骤：
(1)将海藻酸钠、1-乙基-(3-二甲基氨基丙基)碳二亚胺盐酸盐和3-氨基苯硼酸溶解于去离子水中进行搅拌反应，然后将反应溶液依次进行透析、冷冻干燥，得到固形物海藻酸钠苯硼酸；
其中，上述溶解为在1000rpm转速下搅拌10min；
(2)将所述海藻酸钠苯硼酸溶解于虾青素DHA单酯溶液中进行磁力搅拌混匀，混匀后利用减压真空浓缩除去溶剂，得到Alg/PBA-Asta-C22:6；
(3)将所述Alg/PBA-Asta-C22:6溶于去离子水中，然后向其中添加氯化钙溶液，搅拌形成均一水凝胶，得到所述ROS响应型虾青素抗炎水凝胶。
有益效果：本发明前期研究发现经过对游离虾青素进行酯化获得的虾青素DHA单酯(Asta-C22:6)可有效提高虾青素的稳定性和生物利用度，进而本发明以海藻酸钠为前体药物，通过接枝ROS响应官能团(3-氨基苯硼酸,PBA)制备了新型抗炎ROS响应型海藻酸氨基苯硼酸衍生物水凝胶本发明所制得的Alg/PBA，可用于高效递送虾青素及酯化态虾青素，并显著响应生物体内、体外的ROS。有效实现所递送的虾青素在生物体内高水平ROS部位发挥抗氧化效果，从而减少ROS对细胞的损伤，抑制生物体内炎症的发展。并且，本发明所制备的ROS响应水凝胶在体外表现出良好的H2O2响应，并探究了其对斑马鱼体内不同炎症改善效果。另外，本发明所构建的新型抗炎虾青素材料可用于新型虾青素功能食品或外敷商品(如虾青素饮品、虾青素抗炎精华等)，实现虾青素的高效、稳定应用。
优选的，步骤(1)中所述海藻酸钠、1-乙基-(3-二甲基氨基丙基)碳二亚胺盐酸盐、3-氨基苯硼酸和去离子水的添加量之比为(1～4g)：(1～6g)：(0.5～1.0g)：(200～500mL)。
有益效果：本发明中选用的材料前体是海藻酸钠。海藻酸钠是一种广泛存在的生物多糖。它是一种阴离子聚电解质天然多糖，由不同比例的β-D-甘露糖醛酸(M)和α-L-谷醛酸(G)组成。它可以与离子交联剂(如Ca2+、Zn2+或Cu2+)相互作用形成水凝胶，其中氯化钙是最常用于形成海藻酸水凝胶的离子交联剂之一。本发明中的海藻酸钠能实现对虾青素的良好包载，可用于虾青素的体内递送。
本发明中选用的ROS响应官能团为苯硼酸。在氧气环境下，苯硼酸或苯硼酸酯易被过氧化氢氧化，导致碳硼键断裂，生成硼酸和苯酚，因此，本发明将苯硼酸或苯硼酸酯作为ROS响应性触发基团，构建具有ROS响应性的海藻酸钠-虾青素递送体系，使其在生物体内有更好的抑制炎症效果。
此外，海藻酸钠可提供大量的-COOH与苯硼酸的氨基发生酰胺化反应，将苯硼酸接枝在海藻酸钠中，并通过Ca2+交联制备得到海藻酸氨基苯硼酸衍生物水凝胶(Alg/PBA)，水凝胶包载游离虾青素及酯化态虾青素，并显著响应生物体内、体外的高水平ROS。有效实现水凝胶在高水平ROS位置快速降解，使所递送的虾青素释放，从而在生物体内高水平ROS部位发挥抗氧化效果，实现减少ROS对细胞的损伤，抑制生物体内炎症发展的目标。
本发明中的1-乙基-(3-二甲基氨基丙基)碳二亚胺盐酸盐作为缩合反应催化剂，可以活化羧基促使与氨基的缩合反应，进而高效合成目标产物。
优选的，步骤(1)中所述搅拌反应过程中搅拌速率为1000rpm，时间为24h，温度为室温，具体为20～25℃；
所述透析使用3500Da透析膜，透析时间为7天；
所述冷冻干燥温度为-60℃，时间为48h。
优选的，步骤(2)中所述海藻酸钠苯硼酸与虾青素DHA单酯溶液的添加量之比为(1～2)g：(100～500)mL。
优选的，所述虾青素DHA单酯溶液为虾青素DHA单酯的乙醇溶液，且所述虾青素DHA单酯与乙醇的添加量之比为(10～50)mg：(5～25)mL。
优选的，步骤(2)中所述磁力搅拌时间为30～50min，温度为20～25℃；
所述减压真空浓缩过程中，真空度为30mmhg，温度为25℃，时间为30～60min。
优选的，步骤(3)所述Alg/PBA-Asta-C22:6、离子水与氯化钙溶液添加量之比为：1～5g：100～500mL：20mL；
所述氯化钙溶液中，氯化钙与水质量比为(0.1～1):(20～200)。
优选的，步骤(3)所述搅拌速率为1000rpm，时间为10min。
一种由上述制备方法制备得到的ROS响应型虾青素抗炎水凝胶。
一种ROS响应型虾青素抗炎水凝胶在功能食品或外敷商品中的应用。
本发明公开了一种ROS响应型虾青素抗炎水凝胶及其制备方法与应用，以化学改性的方式，合成了具有新型ROS响应型虾青素抗炎水凝胶(Alg/PBA-Asta-C22:6水凝胶)。本发明以海藻酸钠为前体药物，通过接枝ROS响应官能团(3-氨基苯硼酸，PBA)制备了新型抗炎ROS响应型海藻酸氨基苯硼酸衍生物水凝胶，并利用Alg/PBA对虾青素DHA单酯进行包埋，得到虾青素体水凝胶，其生物适应性更强、稳定性好，合成步骤简单，且初步验证该ROS响应型虾青素抗炎水凝胶具有体外ROS响应效果及生物抗炎性能。
附图说明
为了更清楚地说明本发明实施例或现有技术中的技术方案，下面将对实施例中所需要使用的附图作简单地介绍，显而易见地，下面描述中的附图仅仅是本发明的一些实施例，对于本领域普通技术人员来讲，在不付出创造性劳动性的前提下，还可以根据这些附图获得其他的附图。
图1为本发明实施例1中的Alg/PBA合成路线；
图2为本发明实施例1中的Alg/PBA体外ROS响应效果考察；
图3为本发明实施例1中得到的Alg/PBA-Asta-C22:6水凝胶对由LPS诱导的全身性炎症的改善效果；
图4为本发明实施例1中得到的Alg/PBA-Asta-C22:6水凝胶对CuSO4诱导的肝部炎症的改善效果；
图5为本发明实施例1中得到的Alg/PBA-Asta-C22:6水凝胶对DSS诱导的肠道炎症的改善效果。
具体实施方式
下面将结合本发明实施例中的附图，对本发明实施例中的技术方案进行清楚、完整地描述，显然，所描述的实施例仅仅是本发明一部分实施例，而不是全部的实施例。基于本发明中的实施例，本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例，都属于本发明保护的范围。
为使本发明的上述目的、特征和优点能够更加明显易懂，下面结合附图和具体实施方式对本发明作进一步详细的说明。
本发明实施例中的室温指20-25℃左右。
实施例1
一种ROS响应型虾青素抗炎水凝胶(Alg/PBA-Asta-C22:6)的制备方法，如图1所示，包括以下步骤：
1)分别称取海藻酸钠2g、1-乙基-(3-二甲基氨基丙基)碳二亚胺盐酸盐(EDC·HCl)1.92g和3-氨基苯硼酸0.78g，在1000rpm转速下搅拌10min，使上述原料溶解于200mL去离子水中，然后在室温下继续以1000rpm搅拌反应24h；
2)将反应后的反应混合物置于3500Da透析膜中透析7天，然后在冷冻干燥器中-60℃冻干48h后收集固形物海藻酸钠苯硼酸(Alg/PBA)，置于干燥器中常温保存；
3)称取虾青素DHA单酯(Asta-C22:6)10mg，并用5mL乙醇溶解，得到Asta-C22:6溶液；
4)取1g步骤(2)得到的Alg/PBA溶解在100mL步骤(3)得到的Asta-C22:6溶液中，在温度为23℃条件下磁力搅拌40min，复溶获得Alg/PBA-Asta-C22:6均匀乳液，然后在真空度为30mmhg，温度为25℃条件下进行减压真空浓缩45min。除去乙醇溶液，获得Alg/PBA-Asta-C22:6，放置-20℃保存；
5)取1g步骤(4)中得到的Alg/PBA-Asta-C22:6溶于100mL去离子水中，形成均一溶液；
6)取0.1g氯化钙溶解在20mL离子水中，得到氯化钙溶液，然后取20mL氯化钙溶液加入至步骤(5)所得均一溶液中，在1000rpm转速下搅拌10min，形成均一水凝胶，即ROS响应型虾青素抗炎水凝胶(Alg/PBA-Asta-C22:6水凝胶)。
实施例2
一种ROS响应型虾青素抗炎水凝胶(Alg/PBA-Asta-C22:6)的制备方法，包括以下步骤：
1)分别称取海藻酸钠1g、1-乙基-(3-二甲基氨基丙基)碳二亚胺盐酸盐(EDC·HCl)0.96g和3-氨基苯硼酸0.34g，在1000rpm转速下搅拌10min，使上述原料溶解于100mL去离子水中，然后在室温下继续以1000rpm搅拌反应24h；
2)将反应后的反应混合物置于3500Da透析膜中透析7天，然后在冷冻干燥器中-60℃冻干48h后收集固形物海藻酸钠苯硼酸(Alg/PBA)，置于干燥器中常温保存；
3)称取虾青素DHA单酯(Asta-C22:6)10mg，并用5mL乙醇溶解，得到Asta-C22:6溶液；
4)取1g步骤(2)得到的Alg/PBA溶解在100mL步骤(3)得到的Asta-C22:6溶液中，在温度为20℃条件下磁力搅拌50min，复溶获得Alg/PBA-Asta-C22:6均匀乳液，然后在真空度为30mmhg，温度为25℃条件下进行减压真空浓缩30min，除去乙醇溶液，获得Alg/PBA-Asta-C22:6，放置-20℃保存；
5)取1g步骤(4)中得到的Alg/PBA-Asta-C22:6溶于100mL去离子水中，形成均一溶液；
6)取0.1g氯化钙溶解在20mL离子水中，得到氯化钙溶液，然后取20mL氯化钙溶液加入至步骤(5)所得均一溶液中，在1000rpm转速下搅拌10min，形成均一水凝胶，即ROS响应型虾青素抗炎水凝胶(Alg/PBA-Asta-C22:6水凝胶)。
实施例3
一种ROS响应型虾青素抗炎水凝胶(Alg/PBA-Asta-C22:6)的制备方法，包括以下步骤：
1)分别称取海藻酸钠2g、1-乙基-(3-二甲基氨基丙基)碳二亚胺盐酸盐(EDC·HCl)1.92g和3-氨基苯硼酸0.78g，在1000rpm转速下搅拌10min，使上述原料溶解于200mL去离子水中，然后在室温下继续以1000rpm搅拌反应24h；
2)将反应后的反应混合物置于3500Da透析膜中透析7天，然后在冷冻干燥器中-60℃冻干48h后收集固形物海藻酸钠苯硼酸(Alg/PBA)，置于干燥器中常温保存；
3)称取虾青素DHA单酯(Asta-C22:6)10mg，并用5mL乙醇溶解，得到Asta-C22:6溶液；
4)取0.1g步骤(2)得到的Alg/PBA溶解在10mL步骤(3)得到的Asta-C22:6溶液中，在温度为25℃条件下磁力搅拌30min，复溶获得Alg/PBA-Asta-C22:6均匀乳液，然后在真空度为30mmhg，温度为25℃条件下进行减压真空浓缩60min，除去乙醇溶液，获得Alg/PBA-Asta-C22:6，放置-20℃保存；
5)取0.1g步骤(4)中得到的Alg/PBA-Asta-C22:6溶于10mL去离子水中，形成均一溶液；
6)取0.01g氯化钙溶解在2mL离子水中，得到氯化钙溶液，然后取2mL氯化钙溶液加入至步骤(5)所得均一溶液中，在1000rpm转速下搅拌10min，形成均一水凝胶，即ROS响应型虾青素抗炎水凝胶(Alg/PBA-Asta-C22:6水凝胶)。
技术效果：
1.取三份相同的实施例1所得水凝胶，分别置于PBS溶液、PBS+1×10-3mM H2O2溶液和PBS+1×10-2mM H2O2溶液中，观察水凝胶降解速率，结果如图2所示。
可以看出，通过在体外构建不同浓度的H2O2环境，可以观察到所构建的Alg/PBA在含有H2O2的溶液中发生降解(图2a)，且其降解速率与H2O2浓度正相关。此现象可初步判断Alg/PBA在体外有一定的ROS环境响应性。
2.构建三种斑马鱼炎症模型并验证实施例1制备的新型ROS响应型虾青素抗炎水凝胶(Alg/PBA-Asta-C22:6)对斑马鱼体内炎症的改善效果：
实验收集半小时内产受精鱼卵，在放入培养皿前将受精鱼卵放置于Holt buffer溶液中去除死亡胚胎及粪便等污染物，然后更换Holt buffer溶液，放入含有Holtbuffer溶液的直径10cm培养皿中，再放入28.5℃恒温培养箱中，每日为胚胎换液1次；
(1)使用荧光显微镜，仔细挑选4hpf发育正常的胚胎，挑选后胚胎放入12孔板中，设置对照组、模型组(受试1μg/mL LPS(脂多糖)构建斑马鱼全身炎症模型)和样品组(Alg/PBA-Asta-C22:6)。每组三个平行孔，每孔30个，加入3mL Holtbuffer溶液，在28.5℃下培养至6dpf。配制含有25μg/mL虾青素当量的Alg/PBA-Asta-C22:6的胚胎培养液，用于培养样品组斑马鱼。使用ROS活性氧检测试剂盒，用于标记斑马鱼体内ROS水平，并利用Image J对荧光强度进行计数，结果如图3所示。
(2)使用荧光显微镜，仔细挑选4hpf发育正常的胚胎，挑选后胚胎放入12孔板中，设置对照组、模型组(受试3.2μg/mL CuSO4构建斑马鱼全身炎症模型)和样品组(Alg/PBA-Asta-C22:6)。除对照组外，每组受试3.2μg/mL CuSO4构建斑马鱼急性肝损伤模型，每组三个平行孔，每孔30个，加入3mL Holtbuffer液，在28.5℃下培养至6dpf。配制含有25μg/mL虾青素当量的Alg/PBA-Asta-C22:6的胚胎培养液，用于培养样品组斑马鱼。使用ROS活性氧检测试剂盒，用于标记斑马鱼体内ROS水平，并利用Image J对荧光强度进行计数，结果如图4所示。
(3)使用荧光显微镜，仔细挑选4hpf发育正常的胚胎，挑选后胚胎放入12孔板中，设置对照组、模型组(受试3％v/v DSS(葡聚糖硫酸钠)构建斑马鱼全身炎症模型)和样品组。除对照组外，每组受试3％DSS构建斑马鱼溃疡性结肠炎模型。每组三个平行孔，每孔30个，加入3mL Holt buffer液。28.5℃下培养至6dpf。配制含有25μg/mL虾青素当量的Alg/PBA-Asta-C22:6的胚胎培养液，用于培养样品组斑马鱼。使用中性红染色标记具有酸性pH的健康溶酶体的数量。将中性红染液在胚胎培养液中配置成5μg/mL的工作液。将12孔板中的胚胎培养液除去，每孔中加入1mL中性红工作液，染色1h。染色完成后，除去染液，用胚胎培养液漂洗2-3次。漂洗完成后，重新加入新的胚胎培养液。幼鱼用MS-222麻醉，使用荧光显微镜进行观察，结果如图5所示。
本发明通过构建斑马鱼炎症改善效果筛选平台，考察其对不同炎症改善效果。可知Alg/PBA-Asta-C22:6可有效改善斑马鱼体内由LPS诱导的全身性炎症、CuSO4诱导的肝部炎症及DSS诱导的肠道炎症(如图3-5所示)。主要表现为斑马鱼体内ROS水平的急剧降低进一步促使斑马鱼炎症效果的改善。并且，通过进一步地构建C57BL/6J小鼠溃疡性结肠炎模型，验证了新型抗炎虾青素递送体系(Alg/PBA-Asta-C22:6)对小鼠溃疡性结肠炎有显著的改善效果。
以上所述的实施例仅是对本发明的优选方式进行描述，并非对本发明的范围进行限定，在不脱离本发明设计精神的前提下，本领域普通技术人员对本发明的技术方案做出的各种变形和改进，均应落入本发明权利要求书确定的保护范围内。
Claims (10)
1.一种ROS响应型虾青素抗炎水凝胶的制备方法，其特征在于，包括以下步骤：
(1)将海藻酸钠、1-乙基-(3-二甲基氨基丙基)碳二亚胺盐酸盐和3-氨基苯硼酸溶解于去离子水中进行搅拌反应，然后将反应溶液依次透析、冷冻干燥，得到固形物海藻酸钠苯硼酸；
(2)将所述海藻酸钠苯硼酸溶解于虾青素DHA单酯溶液中进行磁力搅拌混匀，后利用减压真空浓缩除去体系中的溶剂，得到Alg/PBA-Asta-C22:6；
(3)将所述Alg/PBA-Asta-C22:6溶于去离子水中，然后向其中添加氯化钙溶液，搅拌形成均一水凝胶，得到所述ROS响应型虾青素抗炎水凝胶。
2.根据权利要求1所述的一种ROS响应型虾青素抗炎水凝胶的制备方法，其特征在于，步骤(1)中所述海藻酸钠、1-乙基-(3-二甲基氨基丙基)碳二亚胺盐酸盐、3-氨基苯硼酸和去离子水的添加量之比为(1～4g)：(1～6g)：(0.5～1.0g)：(200～500mL)。
3.根据权利要求1所述的一种ROS响应型虾青素抗炎水凝胶的制备方法，其特征在于，步骤(1)中所述搅拌反应过程中搅拌速率为1000rpm，时间为24h，温度为20～25℃；
所述透析使用3500Da透析膜，透析时间为7天；
所述冷冻干燥温度为-60℃，时间为48h。
4.根据权利要求1所述的一种ROS响应型虾青素抗炎水凝胶的制备方法，其特征在于，步骤(2)中所述海藻酸钠苯硼酸与虾青素DHA单酯溶液的添加量之比为(1～2)g：(100～500)mL。
5.根据权利要求4所述的一种ROS响应型虾青素抗炎水凝胶的制备方法，其特征在于，所述虾青素DHA单酯溶液为虾青素DHA单酯的乙醇溶液，且所述虾青素DHA单酯与乙醇的添加量之比为(10～50)mg：(5～25)mL。
6.根据权利要求1所述的一种ROS响应型虾青素抗炎水凝胶的制备方法，其特征在于，步骤(2)中所述磁力搅拌时间为30～50min，温度为20～25℃；
所述减压真空浓缩过程中，真空度为30mmhg，温度为25℃，时间为30～60min。
7.根据权利要求1所述的一种ROS响应型虾青素抗炎水凝胶的制备方法，其特征在于，步骤(3)所述Alg/PBA-Asta-C22:6、离子水与氯化钙溶液添加量之比为：1～5g：100～500mL：20mL；
所述氯化钙溶液中，氯化钙与水质量比为(0.1～1):(20～200)。
8.根据权利要求1所述的一种ROS响应型虾青素抗炎水凝胶的制备方法，其特征在于，步骤(3)所述搅拌速率为1000rpm，时间为10min。
9.一种如权利要求1-8任一项所述的制备方法制备得到的ROS响应型虾青素抗炎水凝胶。
10.一种如权利要求9所述的ROS响应型虾青素抗炎水凝胶在功能食品或外敷商品中的应用。
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