CN114452268A - 介孔聚多巴胺载花青素纳米粒的制备方法 - Google Patents
介孔聚多巴胺载花青素纳米粒的制备方法 Download PDFInfo
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Abstract
本发明涉及纳米材料技术领域,公开了一种介孔聚多巴胺载花青素纳米粒的制备方法,制备出的纳米粒包括质量比为60~70:5~8:4~9的介孔聚多巴胺纳米粒、花青素和聚乙二醇改性壳聚糖,所述介孔聚多巴胺纳米粒作为载体,通过物理和化学吸附吸附所述花青素,所述聚乙二醇改性壳聚糖包裹在最外层。本纳米颗粒可保持花青素较高的DPPH、羟基自由基清除活性及抗癌活性,增加花青素的稳定性。
Description
分案说明
本发明为申请日为2020年12月31日,申请号为2020116310959,发明名称为“介孔聚多巴胺载花青素纳米粒及其制备方法”的分案申请。
技术领域
本发明涉及纳米材料技术领域,具体涉及一种介孔聚多巴胺载花青素纳米粒的制备方法。
背景技术
花青素是一类广泛存在于植物的花、果实和叶中的水溶性天然色素,属于黄酮类多酚化合物,桑椹是一种药食两用中药材,其果实中富含花青素类化合物,是天然色素的重要来源之一,具有抗氧化、降血脂、抗动脉粥样硬化、增强免疫、改善贫血及抗肿瘤等保健和药理功能。然而,桑椹花青素不稳定,温度、浓度、光照、pH、酶、氧气、抗坏血酸、糖及其降解产物、金属离子和自身结构等内外因素都能影响花青素的稳定性。,因此需要制备合适的药物递送系统以解决上述问题,以改善桑椹花青素的稳定性,防止药物进入生物体后被水解、氧化而失活,并延长其体内释放时间。
聚多巴胺(PDA)是天然生物色素-黑色素的主要成分,可通过多巴胺的氧化自聚合反应得到,具有良好的稳定性、生物可降解性、生物相容性和光热转换特性,是一种比较理想的载体材料。聚多巴胺具有粘附性,可包覆在多种材料表面。聚多巴胺还具有pH敏感性,可在肿瘤的微酸性环境中解聚。通过模板法可以制备得到介孔聚多巴胺纳米粒,介孔聚多巴胺纳米粒(MPDA)因其具有孔道结构、较高比表面积,可以高效负载药物,还具有良好的光热转换性能。壳聚糖是一类由氨基葡萄糖组成的阳离子聚合物,具有很好的生物相容性、低毒性和可生物降解性,且具有肠粘膜粘附的特性,作为药物辅料有利于药物的口服吸收。对壳聚糖进行聚乙二醇修饰,可以减少血浆蛋白对壳聚糖包衣介孔聚多巴胺纳米粒的吸附作用,从而减少巨噬细胞对壳聚糖包衣介孔聚多巴胺纳米粒的摄取,延缓载药纳米粒从血浆中被清除的过程,并通过“增强的透过及滞留效应”,进一步提高壳聚糖介孔聚多巴胺纳米粒的被动靶向功能。
发明内容
发明目的:针对现有技术中存在的问题,本发明提供一种介孔聚多巴胺载花青素纳米粒的制备方法,可保持花青素较高的DPPH、羟基自由基清除活性及抗癌活性,增加花青素的稳定性。
技术方案:本发明提供了一种介孔聚多巴胺载花青素纳米粒,其特征在于,包括质量比为60~70:5~8:4~9的介孔聚多巴胺纳米粒、花青素和聚乙二醇改性壳聚糖,所述介孔聚多巴胺纳米粒作为载体,通过物理和化学吸附吸附所述花青素,所述聚乙二醇改性壳聚糖包裹在最外层。
优选地,所述花青素为桑葚花青素。
本发明还提供了一种介孔聚多巴胺载花青素纳米粒的制备方法,具体包括以下步骤实施:(1)向乙醇水溶液中加入盐酸多巴胺和Pluronic F127,室温搅拌,然后逐滴加入TMB,形成白色乳液,然后加入氨水溶液搅拌,离心后将沉淀用乙醇和水超声洗涤数次,离心得到介孔聚多巴胺纳米粒,标记为MPDA;其中,盐酸多巴胺、Pluronic F127、TMB以及氨水溶液的质量体积比为0.2~0.5 g:0.8~1.2 g:0.8~1.0 mL:4.0~5.0 mL;(2)将步骤(1)所得介孔聚多巴胺纳米粒与花青素粉末加至去离子水中,在室温搅拌反应,离心,用去离子水冲洗数次,即得到载花青素纳米粒,标记为MPDA@MAS;其中,介孔聚多巴胺纳米粒与花青素粉末的质量比为12~14:1;(3)称取一定量壳聚糖和聚乙二醇,溶解于稀乙酸溶液中混合均匀,在室温下搅拌过夜,即得到聚乙二醇改性壳聚糖溶液;(4)将步骤(2)得到的所得载花青素纳米粒溶于乙酸水溶液中,逐滴加入步骤(3)所得聚乙二醇改性壳聚糖溶液,在室温下搅拌,离心,冷冻干燥,即得介孔聚多巴胺载花青素纳米粒PEG-CS@MPDA@MAS。
优选地,步骤(1)中,乙醇水溶液中,乙醇和水的体积比为1:1。
优选地,步骤(3)中,壳聚糖与聚乙二醇的质量比为1:0.2~0.3。
优选地,步骤(3)中,稀乙酸水溶液的质量分数为1~2%。
优选地,步骤(4)中,乙酸水溶液的质量分数为0.5~1%。
优选地,步骤(4)中,冷冻干燥温度为-40~-70 ℃,冷冻干燥时间为12~24 h。
有益效果:与现有技术相比,本发明具有以下有益效果:
(1)本发明以聚多巴胺为基础材料,通过介孔聚多巴胺纳米粒的合成、花青素的负载、改性壳聚糖分子的包覆,构建了一种可提高桑椹花青素稳定性的以改性壳聚糖为包衣的载药介孔聚多巴胺纳米粒,由于外层壳聚糖也具有抗氧化及抗癌作用,可避免花青素暴露于空气中,使得本载花青素纳米粒可保持花青素较高的DPPH、羟基自由基清除活性及抗癌活性,增加花青素的稳定性。
(2)载体介孔聚多巴胺(MPDA),具有较高的比表面积和纳米孔道结构,且自身具有很强的吸附能力,可通过花青素之间的离子键合和π-π堆积大幅度提高桑椹花青素的负载效率,以解决花青素易氧化需大量给药问题。
(3)改性壳聚糖能被人体吸收利用,具有良好的生物相容性,可生物降解,降解过程中产生的壳寡糖在体内不积累,几乎无免疫原性,同时具有较好的水溶性,通过壳聚糖修饰将介孔聚多巴胺纳米载体表面电性改变为正电,增加介孔聚多巴胺载体对肿瘤细胞的粘附性。壳聚糖可以吸附在肠道,延缓排出体外,使得人体吸收的花青素较多,提高生物利用率,且外表包裹壳聚糖可以提高颗粒储藏稳定性。
(4)本发明的介孔聚多巴胺载桑椹花青素纳米粒,由于外层壳聚糖的而存在,在肠液中可以缓慢降解外层壳聚糖及聚多巴胺层,在胃部消化过程中可延缓胃酸对纳米颗粒的溶蚀,并在小肠液中缓慢释放,控制花青素在胃肠道中的传递过程。
(5)本发明构建的介孔聚多巴胺载体安全,无毒性,且制备简单,成分单一,能够提高花青素的稳定性,便于贮存。
附图说明
图1介孔聚多巴胺载体及介孔聚多巴胺载桑椹花青素纳米粒的粒径分布图;
图2介孔聚多巴胺载体及介孔聚多巴胺载桑椹花青素纳米粒的透射电镜图;
图3介孔聚多巴胺MPDA的氮气吸附/脱附曲线图;
图4空白载体对人正常肝细胞LO2的生物安全性考察;
图5介孔聚多巴胺载桑椹花青素纳米粒在模拟胃液、肠液中的缓释曲线图。
图6介孔聚多巴胺载桑椹花青素纳米粒抗氧化性研究;
图7介孔聚多巴胺载桑椹花青素纳米粒稳定性研究;
图8介孔聚多巴胺纳米粒对人肺癌细胞A549的细胞毒性作用。
具体实施方式
下面结合附图对本发明进行详细的介绍。
实施方式1:
本实施方式提供了一种介孔聚多巴胺载桑椹花青素纳米粒PEG-CS@MPDA@MAS的制备方法,具体按以下步骤实施:
步骤1,MPDA的合成
向乙醇水(1:1,v/v)的混合溶液中加入0.3 g盐酸多巴胺和0.8 g PluronicF127,室温搅拌,然后逐滴加入1.0 mL TMB,形成白色乳液;加入4.0 mL氨水溶液,50 ℃搅拌30 min,离心后将沉淀用乙醇和水超声洗涤3次,离心得到介孔聚多巴胺纳米粒,标记为MPDA;
步骤2,MPDA@MAS的合成
将介孔聚多巴胺纳米粒与桑椹花青素粉末按质量比为12:1的比例加至去离子水中,在室温搅拌反应24 h,离心,用去离子水冲洗3次,即得到载桑椹花青素纳米粒,标记为MPDA@MAS;
步骤3,PEG-CS@MPDA@MAS的合成
称取1 g壳聚糖和0.25 g聚乙二醇,溶解于1.5%稀乙酸溶液中混合均匀,在室温下搅拌过夜,即得到聚乙二醇改性壳聚糖溶液;将载桑椹花青素纳米粒溶于100 mL 0.5%乙酸水中,逐滴加入20 mL聚乙二醇改性壳聚糖溶液,在室温下搅拌,离心,-40 ℃冷冻干燥24h,即得到介孔聚多巴胺载桑椹花青素纳米粒PEG-CS@MPDA@MAS。
制得的介孔聚多巴胺载桑椹花青素纳米粒PEG-CS@MPDA@MAS,包括质量比为60:5:4的介孔聚多巴胺纳米粒、桑椹花青素和聚乙二醇改性壳聚糖,介孔聚多巴胺纳米粒作为载体,通过物理和化学吸附桑椹花青素,聚乙二醇改性壳聚糖包裹在最外层。
实施方式2:
一种介孔聚多巴胺载桑椹花青素纳米粒的制备方法,具体按以下步骤实施:
步骤1,MPDA的合成
向乙醇水(1:1,v/v)的混合溶液中加入0.3 g盐酸多巴胺和1.0 g PluronicF127,室温搅拌,然后逐滴加入1.0 mL TMB,形成白色乳液,加入4.5 mL氨水溶液,50 ℃搅拌40 min,离心后将沉淀用乙醇和水超声洗涤5次,离心得到介孔聚多巴胺纳米粒,标记为MPDA;
步骤2,MPDA@MAS的合成
将介孔聚多巴胺纳米粒与桑椹花青素粉末按质量比为13:1的比例加至去离子水中,在室温搅拌反应12 h,离心,用去离子水冲洗3次,即得到载桑椹花青素纳米粒,标记为MPDA@MAS;
步骤3,PEG-CS@MPDA@MAS的合成
称取1 g壳聚糖和0.2 g聚乙二醇,溶解于2%稀乙酸溶液中混合均匀,在室温下搅拌过夜,即得到聚乙二醇改性壳聚糖溶液;将载桑椹花青素纳米粒溶于100 mL 0.5%乙酸水中,逐滴加入20 mL聚乙二醇改性壳聚糖溶液,在室温下搅拌,离心,-60 ℃冷冻干燥16 h,即得到介孔聚多巴胺载桑椹花青素纳米粒PEG-CS@MPDA@MAS。
制得的介孔聚多巴胺载桑椹花青素纳米粒PEG-CS@MPDA@MAS,包括质量比为65:7:6的介孔聚多巴胺纳米粒、桑椹花青素和聚乙二醇改性壳聚糖,介孔聚多巴胺纳米粒作为载体,通过物理和化学吸附桑椹花青素,聚乙二醇改性壳聚糖包裹在最外层。
实施方式3:
一种介孔聚多巴胺载桑椹花青素纳米粒的制备方法,具体按以下步骤实施:
步骤1,MPDA的合成
向乙醇水(1:1,v/v)的混合溶液中加入0.4 g盐酸多巴胺和1.0 g PluronicF127,室温搅拌,然后逐滴加入0.8 mL TMB形成白色乳液,加入5 mL氨水溶液,40 ℃搅拌40min,离心后将沉淀用乙醇和水超声洗涤5次,离心得到介孔聚多巴胺纳米粒,标记为MPDA;
步骤2,MPDA@MAS的合成
将介孔聚多巴胺纳米粒与桑椹花青素粉末按质量比为14:1的比例加至去离子水中,在室温搅拌反应24 h,离心,用去离子水冲洗3次,即得到载桑椹花青素纳米粒,标记为MPDA@MAS;
步骤3,PEG-CS@MPDA@MAS的合成
称取1 g壳聚糖和0.3 g聚乙二醇,溶解于2%稀乙酸溶液中混合均匀,在室温下搅拌过夜,即得到聚乙二醇改性壳聚糖溶液;将载桑椹花青素纳米粒溶于100 mL 0.5%乙酸水中,逐滴加入20 mL聚乙二醇改性壳聚糖溶液,在室温下搅拌,离心,-70 ℃冷冻干燥12 h,即得到介孔聚多巴胺载桑椹花青素纳米粒PEG-CS@MPDA@MAS。
制得的介孔聚多巴胺载桑椹花青素纳米粒PEG-CS@MPDA@MAS,包括质量比为70:8:7的介孔聚多巴胺纳米粒、桑椹花青素和聚乙二醇改性壳聚糖,介孔聚多巴胺纳米粒作为载体,通过物理和化学吸附桑椹花青素,聚乙二醇改性壳聚糖包裹在最外层。
采用马尔文激光粒度仪对介孔聚多巴胺载体和介孔聚多巴胺载桑椹花青素纳米粒的粒径分布进行分析。将介孔聚多巴胺载体和介孔聚多巴胺载桑椹花青素纳米粒分散于水中,测定其粒径分布,如图1所示,其水动力直径大小分别为120 ± 10 nm和130 ± 10nm。
透射电镜(TEM)观察介孔聚多巴胺载体和介孔聚多巴胺载桑椹花青素纳米粒的形貌:取10μL溶液,滴加在表面碳涂层铜网上,室温条件下自然风干。200KV电压条件下,透射电子显微镜观察纳米颗粒的形貌、粒径和分散情况。载体透射电镜图片如图2(a)所示,制得的MPDA粒径分布范围较窄,粒径均一且表面有明显的孔道结构。介孔聚多巴胺载桑椹花青素纳米粒如图2(b)所示,可以看出纳米粒子粒径均一,形状为球形,由于表面桑椹花青素的吸附及壳聚糖的修饰,规则分布的孔道变得模糊。
MPDA氮气吸附/脱附曲线测定:取烘干的80 mg MPDA样品,仪器测定氮气吸附/脱附曲线,如图3所示,利用BJH法计算出制备的MPDA纳米粒子的比表面积为68.7328 m²/g。
用MTT法考察空白载体对人正常肝细胞LO2的生长抑制作用。使用人正常肝细胞LO2,实验组加入200 μL/孔的不同浓度的空白载体溶液,对照组则加入200 μL培养液,在两种pH条件下,以相对细胞存活率作为考察指标,考察人正常肝细胞LO2在不同浓度条件下的细胞活力。如图4所示,当空白纳米粒浓度达到1000 μg/mL时,人正常肝细胞LO2细胞存活率也均在80%以上,说明载体材料在浓度0.98~1000 μg/mL内具有良好的生物相容性。
采用透析袋法考察介孔聚多巴胺载花青素纳米粒在模拟胃液和模拟肠液中的释放情况。将1 mL介孔聚多巴胺载花青素纳米粒混悬液置于透析袋中,释放介质为模拟人工胃液和人工肠液,于37 ℃下恒温振荡,于不同时间点取样,绘制累计药物释放曲线。实验结果如图5所示,从图5中可以看出介孔聚多巴胺载花青素纳米粒在模拟胃液中释药速率高于在模拟肠液中释药速率,累计释放率大于80%,释放较为完全。且介孔聚多巴胺载花青素纳米粒从实验一开始就缓慢释放,并随着时间的推移逐渐稳定,说明介孔聚多巴胺载花青素纳米粒在花青素控释方面的确有显著效果。
采用DPPH法测定桑椹花青素抗氧化能力。分别吸取2 mL介孔聚多巴胺载桑椹花青素纳米粒混悬液和2 mLDPPH溶液试管中,混合摇匀,在黑暗环境下放置30 min,测其吸光度,Vc溶液作阳性对照。结果如图6所示,随着样品浓度的逐渐增加,各样品对DPPH自由基的清除能力逐渐增强,当添加量在5~20 μg/mL浓度范围内时,清除率的增加趋势变缓,当浓度达到一定水平,清除率将不在增加,而趋于平稳。且在测试浓度范围内,载花青素纳米粒及游离花青素的清除率都高于阳性对照Vc。因此,载花青素纳米粒具有更强的DPPH自由基消除活性。
热稳定性研究:将一定量的介孔聚多巴胺载桑椹花青素纳米粒混悬液置于50 ℃水浴并避光的条件下进行实验,并与未负载的桑椹花青素溶液作对照,分别在第0天,第1天,第2天,第3天,第4天和第5天用紫外分光光度计方法分别测定含量。结果如图7所示,介孔聚多巴胺载桑椹花青素的残留率均高于未负载的桑椹花青素。
通过MTT试验考察了游离花青素、PEG-CS@MPDA@MAS对人肺癌细胞A549癌细胞的毒性作用。结果如图8所示,在两种pH条件下花青素对人肺癌细胞A549表现出明显的剂量依赖性抑制作用。载于载体上后花青素的这种增强的抗肿瘤作用可能是由于螯合的花青素具有优异的抗增殖活性以及花青素和表面改性壳聚糖包衣的协同抗肿瘤作用。
上述实施方式只为说明本发明的技术构思及特点,其目的在于让熟悉此项技术的人能够了解本发明的内容并据以实施,并不能以此限制本发明的保护范围。凡根据本发明精神实质所做的等效变换或修饰,都应涵盖在本发明的保护范围之内。
Claims (8)
1.一种介孔聚多巴胺载花青素纳米粒的制备方法,其特征在于,具体包括以下步骤实施:
(1)向乙醇水溶液中加入盐酸多巴胺和Pluronic F127,室温搅拌,然后逐滴加入TMB,形成白色乳液,然后加入氨水溶液搅拌,离心后将沉淀用乙醇和水超声洗涤数次,离心得到介孔聚多巴胺纳米粒,标记为MPDA;
其中,盐酸多巴胺、Pluronic F127、TMB以及氨水溶液的质量体积比为0.2~0.5 g:0.8~1.2 g:0.8~1.0 mL:4.0~5.0 mL;
(2)将步骤(1)所得介孔聚多巴胺纳米粒与花青素粉末加至去离子水中,在室温搅拌反应,离心,用去离子水冲洗数次,即得到载花青素纳米粒,标记为MPDA@MAS;
其中,介孔聚多巴胺纳米粒与花青素粉末的质量比为12~14:1;
(3)称取一定量壳聚糖和聚乙二醇,溶解于稀乙酸溶液中混合均匀,在室温下搅拌过夜,即得到聚乙二醇改性壳聚糖溶液;
(4)将步骤(2)得到的所得载花青素纳米粒溶于乙酸水溶液中,逐滴加入步骤(3)所得聚乙二醇改性壳聚糖溶液,在室温下搅拌,离心,冷冻干燥,即得介孔聚多巴胺载花青素纳米粒PEG-CS@MPDA@MAS。
2.如权利要求1所述的介孔聚多巴胺载花青素纳米粒的制备方法,其特征在于,步骤(1)中,乙醇水溶液中,乙醇和水的体积比为1:1。
3.如权利要求1所述的介孔聚多巴胺载花青素纳米粒的制备方法,其特征在于,步骤(3)中,壳聚糖与聚乙二醇的质量比为1:0.2~0.3。
4.如权利要求3所述的介孔聚多巴胺载花青素纳米粒的制备方法,其特征在于,步骤(3)中,稀乙酸水溶液的质量分数为1~2%。
5.如权利要求1所述的介孔聚多巴胺载花青素纳米粒的制备方法,其特征在于,步骤(4)中,乙酸水溶液的质量分数为0.5~1%。
6.如权利要求1至5中任意一项所述的介孔聚多巴胺载花青素纳米粒的制备方法,其特征在于,步骤(4)中,冷冻干燥温度为-40~-70 ℃,冷冻干燥时间为12~24 h。
7.如权利要求1至5中任意一项所述的介孔聚多巴胺载花青素纳米粒的制备方法,其特征在于,制备得到的所述介孔聚多巴胺载花青素纳米粒中,包括质量比为60~70:5~8:4~9的介孔聚多巴胺纳米粒、花青素和聚乙二醇改性壳聚糖,所述介孔聚多巴胺纳米粒作为载体,通过物理和化学吸附吸附所述花青素,所述聚乙二醇改性壳聚糖包裹在最外层。
8.如权利要求1至5中任意一项所述的介孔聚多巴胺载花青素纳米粒的制备方法,其特征在于,所述花青素为桑葚花青素。
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