CN107698719A - 一种基于大分子自组装制备水分散性量子点标记分子印迹纳米粒子的方法 - Google Patents
一种基于大分子自组装制备水分散性量子点标记分子印迹纳米粒子的方法 Download PDFInfo
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- CN107698719A CN107698719A CN201711017443.1A CN201711017443A CN107698719A CN 107698719 A CN107698719 A CN 107698719A CN 201711017443 A CN201711017443 A CN 201711017443A CN 107698719 A CN107698719 A CN 107698719A
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Abstract
本发明公开了一种基于大分子自组装制备水分散性量子点标记分子印迹纳米粒子的方法,涉及高分子材料科学、生命健康、自组装等科技领域。本发明首先利用疏水相互作用对量子点进行表面双键改性,提供荧光来源的同时充当交联剂,然后利用双亲大分子、双键改性量子点、模板分子、光引发剂的共组装得到水分散性的量子点标记分子印迹纳米粒子,通过光交联稳定其结构。制备的该纳米粒子可用于水相中对模板分子的特异性识别与检测。该发明结合了纳米材料大比表面积、分子印迹技术选择性好和量子点荧光性能稳定的优点,可以对实际样品中微量的小分子或生物大分子进行高选择性、高灵敏性的快速检测,尤其在环境监测、食品安全、临床分析等方面有着广阔的应用前景。
Description
技术领域
本发明涉及高分子材料科学、生命健康、自组装等科技领域,具体涉及一种基于大分子自组装制备水分散性量子点标记分子印迹纳米粒子的方法
背景技术
大分子自组装自发现伊始就得到了广泛的关注和研究。通过双亲共聚物自组装得到的胶束、囊泡、腔室囊泡等结构已经在生物药物负载及控释、生物成像等方面有众多的研究。随着科技的发展,形态不再是自组装过程中追寻的一个重点,功能性组装体的制备及其应用受到了越来越多的关注。将大分子与其他功能性材料进行多组分杂化自组装是获得功能性组装体的一个重要途径。在众多功能性物质中,无机纳米粒子由于其拥有独特的光、电、磁、催化性质等备受关注,其与双亲聚合物的丰富组装行为更赋予其一些独特的性质,如可加工性、生物相容性、温度及pH响应性、稳定性等。量子点作为一种无机半导体,它的荧光强度约是单个染料分子的20~50倍,并且有荧光寿命长、光化学稳定性好、量子产率高等优点,在物质检测、免疫分析、生物成像领域都有着广阔的应用前景。但是由于未经改性的量子点只能溶于有机溶剂中,无法满足在生物体内检测或成像的要求,其次,由于量子点尺寸在纳米级,存在团聚的风险,且有一定的细胞毒性,因此通常需要对其进行一系列的改性。将双亲共聚物与量子点共组装得到的杂化组装体不仅能解决量子点的这些问题,更赋予组装体一定的功能性。
对特定分子的特异性识别与检测是检测领域的一个重点和难点,在诸多化学领域都有着重要的意义。通过模拟天然受体的分子识别能力,分子印迹技术应运而生。制备分子印迹聚合物主要有以下几个步骤:模板分子与功能单体在共价键或非共价键作用下形成复合物,然后加入交联剂反应后形成交联网状结构,最后将模板分子洗脱,在分子印迹聚合物上形成形状、尺寸、功能基团与模板分子互补的印迹位点。因此,制备的分子印迹聚合物能对模板分子进行特异性识别,与传统检测方法相比具有较好的选择性。分子印迹技术对众多种类的模板分子都具有普适性,对于传统方法难以简便、精确检测的胆固醇、多肽、蛋白质等疾病标记物都有较好的印迹及检测效果。疾病标记物是指当身体出现疾病时在血浆或其他体液中都能检测到的物质,是指示疾病存在的生物化学指标。因此,为了能及时发现疾病的存在,对疾病标记物的检测在生命安全方面有着重要的意义。将疾病标记物作为模板分子,利用双亲共聚物与量子点共组装得到纳米粒子结构,其较大的比表面积同时还可以解决传统分子印迹由于大多数分子识别位点都包埋在高交联密度的聚合物内部而导致的分子印迹材料模板分子洗脱困难、结合容量低、信号响应慢、检测下限高、位点可接近性差以及结合动力学慢等缺点。
本发明首先对量子点进行表面双键化的改性,在提供荧光的同时作为交联剂,利用其与可光交联双亲无规共聚物、模板分子的共组装得到量子点标记的分子印迹纳米粒子,通过光交联增加粒子的稳定性,洗脱后,得到能直接对模板分子进行特异性识别与检测的材料,并且其具有选择性高,吸附速度快,工艺简单,可反复多次使用,环境友好等优点
发明内容
本发明首先制备了表面双键改性的量子点,然后合成了含疏水单元乙烯基咔唑及和亲水单体的双亲聚合物,利用含双键的功能单元对双亲聚合物进行侧链改性得到可光交联双亲无规共聚物。向可光交联双亲无规共聚物、表面双键改性量子点和光引发剂的混合溶液中滴加模板分子水溶液诱导形成纳米粒子,模板分子通过氢键相互作用被包裹在其内部,通过紫外光照使得其内部交联,固定印迹位点,去除模板分子后得到量子点标记分子印迹纳米粒子。模板分子的存在会对量子点的荧光进行猝灭,因此荧光强度较低,去除模板分子后,猝灭作用消失,荧光强度较高,所述方法包括如下步骤:
第一步:表面双键改性量子点的制备
将油酸稳定的量子点分散在四氢呋喃中,向量子点的四氢呋喃溶液中加入含长碳链的乙烯基类单体,搅拌2~6h;
第二步:可光交联双亲无规共聚物的制备
将乙烯基咔唑(NVC)、亲水单体及引发剂溶解在溶剂中,通N2除去体系中的氧气,将反应体系移入油浴中,在60~100℃下搅拌,反应 8~24h,然后,向反应溶液中加入甲基丙烯酸缩水甘油酯(GMA)、三苯基膦和对苯二酚的混合溶液,温度为80~120℃,反应8~24h,通过沉淀,真空烘箱干燥过夜得到可光交联双亲无规共聚物,其分子量在5000~20000;
第三步:水分散性量子点标记分子印迹纳米粒子的制备
将第二步所得到的可光交联双亲无规共聚物溶解在四氢呋喃中,并向其中加入表面双键改性量子点和光引发剂,向上述混合溶液中滴加模板分子水溶液诱导可光交联双亲无规共聚物与模板分子、表面双键改性量子点及光引发剂共组装得到纳米粒子,将上述纳米粒子置于紫外点光源下照射15~30min,再将其反滴定入5~10倍体积的水中,搅拌过夜;
第四步:模板分子的洗脱
向上述水分散液中加入醋酸,洗脱30~60min,离心,再用洗脱液对其进行洗涤直至上层清夜中没有模板分子的紫外吸收,将离心所得沉淀重新分散于水中得到悬浮液,调节pH使得其由悬浮液变为澄清透明的分散液,其可用于对相应模板分子的识别与检测
与现有技术相比,本发明具有如下优点:
(1)将自组装、量子点和分子印迹技术进行有效结合来制备具有分子印迹功能的新型荧光纳米粒子,提出了一条新的制备分子印迹聚合物的方法。
(2)目前分子印迹大多只能在有机相(如氯仿、乙腈、甲苯)中进行聚合和应用,而本发明中分子印迹过程和识别过程均是在水相中进行的,更加环境友好,拓宽了其在生物检测方面的应用。
(3)本发明制得的量子点标记分子印迹纳米粒子对模板分子具有特异的识别能力,且具有选择性高,吸附速度快,工艺简单,可反复多次使用等优点。
附图说明
图1是量子点标记分子印迹纳米粒子的制备示意图;
图2是实施例1中量子点标记分子印迹纳米粒子的TEM照片;
图3是实施例2中量子点标记分子印迹纳米粒子的TEM照片;
具体实施方式
下面结合具体实例,进一步阐述本发明。这些实例仅用于说明本发明而不用于限制本发明的范围。
实施例1
第一步:将ZnCdSe/ZnS溶于四氢呋喃(THF)中,配置成0.09mg mL-1的溶液,然后向其中加入7μL 2-丙烯酸十二烷基酯,避光搅拌过夜;
第二步:将单体丙烯酸(0.3603g,5mmol)、乙烯基咔唑(0.9663g, 5mmol)、偶氮二异丁氰(0.0328g,2%mt%)加入50ml圆底烧瓶中,加入溶剂N,N-二甲基甲酰胺(DMF)15mL,通N2 20min除去溶液中的氧气后,在搅拌状态下,温度保持在80℃在油浴中反应24 h,将单体甲基丙烯酸乙二醇酯(0.711g,5mmol)、三苯基膦(0.0262 g,0.1mmol)和对苯二酚(0.0028g,0.025mmol)溶于5mL DMF中,通过恒压滴液漏斗将其逐滴加入上述聚合物溶液中,在搅拌状态下,温度保持在95℃在油浴中反应12h,用石油醚沉淀三次后,真空烘箱40℃干燥过夜得到可光交联双亲无规共聚物;
第三步:将10mg上述聚合物溶于良溶剂THF中,并向其中加入10 μL光引发剂安息香二甲醚的THF溶液(5mg mL-1),搅拌均匀后,以7μL min-1的速度向其中加入牛血清蛋白水溶液(0.2mg mL-1)诱导组装,搅拌过夜后在365nm的紫外点光源照射下进行光交联,将光交联后的纳米粒子滴加到大量水中进行固定,最后体积为原分散液的五倍;
第四步:向上述分散液中加入醋酸使得分子印迹荧光纳米粒子从水相中分离,用水:醋酸(9:1/v:v)作为洗脱液对沉淀进行洗涤,直至上层清液中不存在模板分子的紫外吸收,并用水对沉淀进行洗涤去除醋酸分子,然后将沉淀悬浮分散在水中,用碳酸钠溶液调节pH至9,向其中加入模板分子,分别测量加入模板分子前后的荧光发射光谱。该实例制备的量子点标记分子印迹纳米粒子的TEM照片如图2所示。
实施例2
第一步:将ZnCdSe/ZnS溶于四氢呋喃(THF)中,配置成0.09mg mL-1的溶液,然后向其中加入7μL 2-丙烯酸十二烷基酯,避光搅拌过夜;
第二步:将单体丙烯酸(0.3603g,5mmol)、乙烯基咔唑(0.9663g, 5mmol)、偶氮二异丁氰(0.0328g,2%mt%)加入50ml圆底烧瓶中,加入溶剂N,N-二甲基甲酰胺(DMF)15mL,通N2 20min除去溶液中的氧气后,在搅拌状态下,温度保持在70℃在油浴中反应24 h,将单体甲基丙烯酸乙二醇酯(0.711g,5mmol)、三苯基膦(0.0262 g,0.1mmol)和对苯二酚(0.0028g,0.025mmol)溶于5mL DMF中,通过恒压滴液漏斗将其逐滴加入上述聚合物溶液中,在搅拌状态下,温度保持在95℃在油浴中反应12h,用石油醚沉淀三次后,真空烘箱40℃干燥过夜得到可光交联双亲无规共聚物;
第三步:将10mg上述聚合物溶于良溶剂THF中,并向其中加入30 μL胆固醇THF溶液(5mg mL-1)和10μL光引发剂安息香二甲醚的 THF溶液(5mg mL-1),搅拌均匀后,以7μL min-1的速度向其中加入水诱导组装,搅拌过夜后在365nm的紫外点光源照射下进行光交联,将光交联后的纳米粒子滴加到大量水中进行固定,最后体积为原分散液的五倍;
第四步:向上述分散液中加入醋酸使得分子印迹荧光纳米粒子从水相中分离,用水:醋酸(9:1/v:v)作为洗脱液对沉淀进行洗涤,直至上层清液中不存在模板分子的紫外吸收,并用水对沉淀进行洗涤去除醋酸分子,然后将沉淀悬浮分散在水中,用碳酸钠溶液调节pH至9,向其中加入模板分子,分别测量加入模板分子前后的荧光发射光谱。该实例制备的量子点标记分子印迹纳米粒子的TEM照片如图3所示。
实施例3
第一步:将ZnCdSe/ZnS溶于四氢呋喃(THF)中,配置成0.09mg mL-1的溶液,然后向其中加入7μL 2-丙烯酸十二烷基酯,避光搅拌过夜;
第二步:将单体丙烯酸(0.3603g,5mmol)、乙烯基咔唑(0.9663g, 5mmol)、偶氮二异丁氰(0.0328g,2%mt%)加入50ml圆底烧瓶中,加入溶剂N,N-二甲基甲酰胺(DMF)15mL,通N2 20min除去溶液中的氧气后,在搅拌状态下,温度保持在80℃在油浴中反应24 h,将单体甲基丙烯酸乙二醇酯(0.355g,2.5mmol)、三苯基膦(0.0262 g,0.1mmol)和对苯二酚(0.0028g,0.025mmol)溶于5mL DMF中,通过恒压滴液漏斗将其逐滴加入上述聚合物溶液中,在搅拌状态下,温度保持在95℃在油浴中反应12h,用石油醚沉淀三次后,真空烘箱40℃干燥过夜得到可光交联双亲无规共聚物;
第三步:将10mg上述聚合物溶于良溶剂THF中,并向其中加入10 μL光引发剂安息香二甲醚的THF溶液(5mg mL-1),搅拌均匀后,以7μL min-1的速度向其中加入牛血清蛋白水溶液(0.2mg mL-1)诱导组装,搅拌过夜后在365nm的紫外点光源照射下进行光交联,将光交联后的纳米粒子滴加到大量水中进行固定,最后体积为原分散液的五倍;
第四步:向上述分散液中加入醋酸使得分子印迹荧光纳米粒子从水相中分离,用水:醋酸(9:1/v:v)作为洗脱液对沉淀进行洗涤,直至上层清液中不存在模板分子的紫外吸收,并用水对沉淀进行洗涤去除醋酸分子,然后将沉淀悬浮分散在水中,用碳酸钠溶液调节pH至9,向其中加入模板分子,分别测量加入模板分子前后的荧光发射光谱。
实施例4
第一步:将ZnCdSe/ZnS溶于四氢呋喃(THF)中,配置成0.09mg mL-1的溶液,然后向其中加入7μL 2-丙烯酸十二烷基酯,避光搅拌过夜;
第二步:将单体丙烯酸(0.3603g,5mmol)、乙烯基咔唑(0.9663g, 5mmol)、偶氮二异丁氰(0.0328g,2%mt%)加入50ml圆底烧瓶中,加入溶剂N,N-二甲基甲酰胺(DMF)15mL,通N2 20min除去溶液中的氧气后,在搅拌状态下,温度保持在80℃在油浴中反应24 h,将单体甲基丙烯酸乙二醇酯(0.711g,5mmol)、三苯基膦(0.0262 g,0.1mmol)和对苯二酚(0.0028g,0.025mmol)溶于5mL DMF中,通过恒压滴液漏斗将其逐滴加入上述聚合物溶液中,在搅拌状态下,温度保持在95℃在油浴中反应12h,用石油醚沉淀三次后,真空烘箱40℃干燥过夜得到可光交联双亲无规共聚物;
第三步:将10mg上述聚合物溶于良溶剂THF中,并向其中加入10 μL光引发剂安息香二甲醚的THF溶液(5mg mL-1),搅拌均匀后,以7μL min-1的速度向其中加入牛血清蛋白水溶液(0.05mg mL-1)诱导组装,搅拌过夜后在365nm的紫外点光源照射下进行光交联,将光交联后的纳米粒子滴加到大量水中进行固定,最后体积为原分散液的十倍;
第四步:向上述分散液中加入醋酸使得分子印迹荧光纳米粒子从水相中分离,用水:醋酸(9:1/v:v)作为洗脱液对沉淀进行洗涤,直至上层清液中不存在模板分子的紫外吸收,并用水对沉淀进行洗涤去除醋酸分子,然后将沉淀悬浮分散在水中,用碳酸钠溶液调节pH至9,向其中加入模板分子,分别测量加入模板分子前后的荧光发射光谱。
实施例5
第一步:将ZnCdSe/ZnS溶于四氢呋喃(THF)中,配置成0.09mg mL-1的溶液,然后向其中加入7μL 2-丙烯酸十二烷基酯,避光搅拌过夜;
第二步:将单体丙烯酸(0.3603g,5mmol)、乙烯基咔唑(0.9663g, 5mmol)、偶氮二异丁氰(0.0328g,2%mt%)加入50ml圆底烧瓶中,加入溶剂N,N-二甲基甲酰胺(DMF)15mL,通N2 20min除去溶液中的氧气后,在搅拌状态下,温度保持在70℃在油浴中反应24 h,将单体甲基丙烯酸乙二醇酯(0.711g,5mmol)、三苯基膦(0.0262 g,0.1mmol)和对苯二酚(0.0028g,0.025mmol)溶于5mL DMF中,通过恒压滴液漏斗将其逐滴加入上述聚合物溶液中,在搅拌状态下,温度保持在95℃在油浴中反应12h,用石油醚沉淀三次后,真空烘箱40℃干燥过夜得到可光交联双亲无规共聚物;
第三步:将10mg上述聚合物溶于良溶剂THF中,并向其中加入30 μL胆固醇THF溶液(3mg mL-1)和10μL光引发剂安息香二甲醚的 THF溶液(5mg mL-1),搅拌均匀后,以7μL min-1的速度向其中加入水诱导组装,搅拌过夜后在365nm的紫外点光源照射下进行光交联,将光交联后的纳米粒子滴加到大量水中进行固定,最后体积为原分散液的五倍;
第四步:向上述分散液中加入醋酸使得分子印迹荧光纳米粒子从水相中分离,用水:醋酸(9:1/v:v)作为洗脱液对沉淀进行洗涤,直至上层清液中不存在模板分子的紫外吸收,并用水对沉淀进行洗涤去除醋酸分子,然后将沉淀悬浮分散在水中,用碳酸钠溶液调节pH至7,向其中加入模板分子,分别测量加入模板分子前后的荧光发射光谱。
实施例6
第一步:将ZnCdSe/ZnS溶于四氢呋喃(THF)中,配置成0.09mg mL-1的溶液,然后向其中加入7μL 2-丙烯酸十二烷基酯,避光搅拌过夜;
第二步:将单体丙烯酸(0.3603g,5mmol)、乙烯基咔唑(0.9663g, 5mmol)、偶氮二异丁氰(0.0328g,2%mt%)加入50ml圆底烧瓶中,加入溶剂N,N-二甲基甲酰胺(DMF)15mL,通N2 20min除去溶液中的氧气后,在搅拌状态下,温度保持在70℃在油浴中反应24 h,将单体甲基丙烯酸乙二醇酯(0.711g,5mmol)、三苯基膦(0.0262 g,0.1mmol)和对苯二酚(0.0028g,0.025mmol)溶于5mL DMF中,通过恒压滴液漏斗将其逐滴加入上述聚合物溶液中,在搅拌状态下,温度保持在95℃在油浴中反应12h,用石油醚沉淀三次后,真空烘箱40℃干燥过夜得到可光交联双亲无规共聚物;
第三步:将10mg上述聚合物溶于良溶剂THF中,并向其中加入30 μL胆固醇THF溶液(5mg mL-1)和10μL光引发剂安息香二甲醚的 THF溶液(5mg mL-1),搅拌均匀后,以7μL min-1的速度向其中加入水诱导组装,搅拌过夜后在365nm的紫外点光源照射下进行光交联,将光交联后的纳米粒子滴加到大量水中进行固定,最后体积为原分散液的十倍;
第四步:向上述分散液中加入醋酸使得分子印迹荧光纳米粒子从水相中分离,用水:醋酸(9:1/v:v)作为洗脱液对沉淀进行洗涤,直至上层清液中不存在模板分子的紫外吸收,并用水对沉淀进行洗涤去除醋酸分子,然后将沉淀悬浮分散在水中,用碳酸钠溶液调节pH至9,向其中加入模板分子,分别测量加入模板分子前后的荧光发射光谱。
Claims (5)
1.一种基于大分子自组装制备水分散性量子点标记分子印迹纳米粒子的方法,其特征在于具体步骤如下:
第一步:表面双键改性量子点的制备
将油酸稳定的量子点分散在四氢呋喃中,配置量子点浓度为0.05~0.2mg mL-1,向量子点的四氢呋喃溶液中加入含长碳链的乙烯基类单体,搅拌2~6h;含长碳链的乙烯基类单体与量子点的摩尔比为5:1~20:1;
第二步:可光交联双亲无规共聚物的制备
将乙烯基咔唑(NVC)、亲水单体及引发剂溶解在溶剂中,乙烯基咔唑与亲水单体的摩尔比为1:3~2:1,通N2除去体系中的氧气,将反应体系移入油浴中,在60~100℃下搅拌,反应8~24h,然后,向反应溶液中加入甲基丙烯酸缩水甘油酯(GMA)、三苯基膦和对苯二酚的混合溶液;亲水单体和甲基丙烯酸缩水甘油酯的摩尔比为2:1~1:3,三苯基膦和甲基丙烯酸缩水甘油酯的摩尔比为0.02:1~0.06:1,对苯二酚和甲基丙烯酸缩水甘油酯的摩尔比为0.005:1~0.015:1,温度为80~120℃,反应8~24h,通过沉淀,真空烘箱干燥过夜得到可光交联双亲无规共聚物,其分子量在5000~20000;
第三步:水分散性量子点标记分子印迹纳米粒子的制备
将第二步所得到的可光交联双亲无规共聚物溶解在四氢呋喃中,并向其中加入表面双键改性量子点和光引发剂,向上述混合溶液中滴加模板分子水溶液诱导可光交联双亲无规共聚物与模板分子、表面双键改性量子点及光引发剂共组装得到纳米粒子,其中模板分子可以是小分子,如扑热息痛、多巴胺、葡萄糖,也可以是大分子,如牛血清蛋白、血红蛋白、卵清蛋白、溶菌酶、胆固醇、多肽、DNA;将上述纳米粒子置于紫外点光源下照射15~30min,再将其反滴定入5~10倍体积的水中,搅拌过夜;可光交联双亲无规共聚物的浓度为3~10mgmL-1,模板分子溶液的浓度为0.05~0.1mg mL-1,模板分子与可光交联双亲无规共聚物的摩尔比为1:10~1:50,量子点与双亲共聚物摩尔比为1:100~1:200,光引发剂与双亲无规共聚物摩尔比为1:100~1:80;
第四步:模板分子的洗脱
向上述水分散液中加入醋酸,洗脱30~60min,离心,再用洗脱液对其进行洗涤直至上层清夜中没有模板分子的紫外吸收,将离心所得沉淀重新分散于水中得到悬浮液,调节pH使得其由悬浮液变为澄清透明的分散液,分散液的pH为5~12。
2.根据权利要求1所述的一种基于大分子自组装制备水分散性量子点标记分子印迹纳米粒子的方法,第一步中量子点可以是CdS、CdTe/CdS、ZnCdSe/ZnS中的一种,含长碳链的乙烯基类单体可以是丙烯酸十二烷基酯、丙烯酸十六烷基酯中的一种。
3.根据权利要求1所述的一种基于大分子自组装制备水分散性量子点标记分子印迹纳米粒子的方法,第二步中亲水单体可是丙烯酸、甲基丙烯酸中的一种。
4.根据权利要求1所述的一种基于大分子自组装制备水分散性量子点标记分子印迹纳米粒子的方法,第三步中光引发剂可以选择二芳基碘鎓盐、2-羟基-2-甲基-1-苯基丙酮、安息香二甲醚、苯甲酰甲酸甲酯中的一种。
5.根据权利要求1所述的一种基于大分子自组装制备水分散性量子点标记分子印迹纳米粒子的方法第四步中洗脱液是水:乙酸(1:1~1:100/v:v)、甲醇:乙酸(1:1~1:100/v:v)中的一种。
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