CN107502344A - 基于吡咯并吡咯二酮类化合物和四苯乙烯类化合物的多功能有机荧光纳米颗粒及制备和应用 - Google Patents
基于吡咯并吡咯二酮类化合物和四苯乙烯类化合物的多功能有机荧光纳米颗粒及制备和应用 Download PDFInfo
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Abstract
本发明公开了一种基于吡咯并吡咯二酮类化合物和四苯乙烯类化合物的多功能有机荧光纳米颗粒及制备和应用，其由吡咯并吡咯二酮类化合物和四苯乙烯类化合物通过分子自组装形成；该多功能纳米粒子稳定性好，且同时具有双荧光发射及双光子激发诱导荧光发射能力，可实现比率型Hg2+检测以及双模式(双通道和双光子)细胞成像，可广泛应用于环境工程、生物成像以及生物医药等领域。
Description
技术领域
本发明涉及一种自组装有机荧光纳米颗粒，特别涉及一种可以用于Hg2+检测和细胞成像的多功能荧光纳米颗粒及其制备和应用，属于功能材料领域。
背景技术
多功能纳米颗粒在化学/生物传感和生物成像、载药领域得到了广泛的研究(Lee,D.-E.；Koo,H.；Sun,I.-C.；Ryu,J.H.；Kim,K.；Kwon,I.C.Chemical Society Reviews2012,41,2656-2672.)。其中，以纳米颗粒的荧光信号作为监控对象的技术手段，具有操作简单，成本低以及可靠性高的特点(Wolfbeis,O.S.Chemical Society Reviews 2015,44,4743-4768.)。复合荧光纳米颗粒(例如核壳型纳米颗粒)由于具备不同的组分，可实现纳米颗粒的多功能化。目前常见的复合颗粒大多采用有机-无机金属的构建体系，但这些无机金属(多为重金属)对环境和生物具有潜在的危害，这限制了其在传感和生物应用领域的发展。现今，纯有机荧光纳米颗粒的研究得到了广泛的关注(Peng,H.-S.；Chiu,D.T.ChemicalSociety Reviews 2015,44,4699-4722.)。
分子自组装是一种简单有效的水溶性纳米颗粒制备方法，目前利用两亲荧光分子自组装构建荧光纳米颗粒的方法已经见诸报道(Shulov,I.；Arntz,Y.；Mely,Y.；Pivovarenko,V.G.；Klymchenko,A.S.Chemical Communications 2016,52,7962-7965.)。但是，利用自组装方法构建多功能的有机荧光纳米颗粒还是研究空白。大部分荧光分子具有聚集荧光淬灭效应，利用其自组装而成的纳米颗粒没有或只有微弱荧光(Fan, G.；Lin,Y.-X.；Yang,L.；Gao,F.-P.；Zhao,Y.-X.；Qiao,Z.-Y.；Zhao,Q.；Fan,Y.-S.；Chen,Z.；Wang,H.Chemical Communications 2015,51,12447-12450.)。目前报道，有一类荧光分子具有聚集诱导荧光发射效应，这类分子可制备荧光纳米颗粒，用于生物成像(Tang,F.； Wang,C.；Wang,J.S.；Wang,X.Y.；Li,L.D.Acs Applied Materials&Interfaces 2014,6,18337-18343.)。在已报道的荧光分子中，四苯乙烯(TPE)分子是一种典型的聚集诱导发光分子，其自组装后可获得稳定的荧光纳米颗粒(Tang,F.；Wang,C.；Wang,J.S.； Wang,X.Y.；Li,L.D.Acs Applied Materials&Interfaces 2014,6,18337-18343.)。吡咯并吡咯二酮(DPP)分子同时具有Hg2+识别能力和双光子吸收性质(Nie,K.；Dong,B.；Shi, H.；Liu,Z.；Liang,B.Analytical Chemistry 2017,89,2928-2936)。但是到目前为止，鲜有通过自装置制备有机多功能荧光纳米颗粒的报道，因为稳定性得不到保证，且容易出现自组装后未见荧光或荧光微弱现象，难以实际应用。现有技术中未见将 TPE和DPP通过共混自组装，制备出可同时用于传感和成像的多功能的荧光纳米颗粒。
发明内容
针对现有技术存在的缺陷，本发明的第一个目的是在于提供一种稳定性好，且同时具有双荧光发射及双光子激发诱导荧光发射能力的多功能有机荧光纳米颗粒。
本发明的第二个目的是在于提供一种简单、低成本的制备所述多功能有机荧光纳米颗粒的方法。
本发明的第三个目的是在于提供一种多功能有机荧光纳米颗粒在检测汞离子或细胞成像中的应用，可以应用于对Hg2+的比率型检测，也可以应用于细胞的双通道成像和双光子成像。
为了实现上述技术目的，本发明提供了一种基于吡咯并吡咯二酮类化合物和四苯乙烯类化合物的多功能有机荧光纳米颗粒，其由吡咯并吡咯二酮类化合物和四苯乙烯类化合物通过分子自组装形成；
所述四苯乙烯类化合物具有式1结构：
所述吡咯并吡咯二酮类化合物具有式2结构：
其中，R和R1独立选自亲水基团，R2为噻吩基、呋喃基、吡咯基、吡啶基或芳基。
优选的方案，吡咯并吡咯二酮类化合物与四苯乙烯类化合物的摩尔比为 1:3～5。最优选的摩尔比为1:4。
优选的方案，R和R1独立选自烷氧链、糖类基团或其他水溶性基团。
优选的方案，多功能有机荧光纳米颗粒具有双荧光发射和双光子吸收功能。
本发明还提供了一种基于吡咯并吡咯二酮类化合物和四苯乙烯类化合物的多功能有机荧光纳米颗粒的制备方法，该方法是将吡咯并吡咯二酮类化合物和四苯乙烯类化合物加入水中，超声处理，即得。
优选的方案，吡咯并吡咯二酮类化合物和四苯乙烯类化合物在水中的总浓度为30～60μM/L。
优选的方案，超声处理时间为20～40min。
本发明提供了所述基于吡咯并吡咯二酮类化合物和四苯乙烯类化合物的多功能有机荧光纳米颗粒的应用，将其应用于对Hg2+的比率型检测，或者应用于细胞的双通道成像和双光子成像。
本发明的吡咯并吡咯二酮类化合物和四苯乙烯类化合物的制备都可以借鉴现有的方法制备得到，如吡咯并吡咯二酮类化合物的制备是以具有N原子未修饰内酰胺结构的(呋喃基、吡啶基、吡咯基、苯基或噻吩基等)吡咯并吡咯二酮分子为原料，通过与卤代化合物的一步取代反应制备得到。四苯乙烯类化合物是以4-(1,2,2-三苯基乙烯基)苯酚分子为原料，通过与卤代化合物、氨基化合物、环氧基化合物或羧基化合物等任一底物经过一步反应制备得到。
本发明的多功能有机荧光纳米颗粒选择吡咯并吡咯二酮类化合物和四苯乙烯类化合物通过共组装成复合纳米颗粒，四苯乙烯类化合物形成的亲油内腔可抑制吡咯并吡咯二酮类化合物的过度聚集，TPE类分子还起到维持纳米颗粒的稳定结构的作用，能保持纳米颗粒的稳定性，从而可同时保存两种荧光组分的各种性能，用于传感及生物成像。
本发明的技术方案将亲水修饰的四苯乙烯分子与亲水修饰的吡咯并吡咯二酮分子通过自组装获得稳定的荧光纳米颗粒。四苯乙烯分子其本身是一种典型的聚集诱导发光(AIE)分子，本发明将其荧光作为内参，同时引入一种吡咯并吡咯二酮类荧光分子作为被分析物的识别单元，从而构建一种比率型的纳米传感器，可以用于汞离子的比率型检测。同时，该荧光纳米颗粒拥有两种不同的荧光发射，可用于细胞的双荧光成像。因此，本发明利用四苯乙烯类分子和吡咯并吡咯二酮类分子共混自组装，可获得用于比率型Hg2+检测以及双模式(双通道和双光子) 细胞成像的多功能荧光纳米颗粒。
相对现有技术，本发明的技术方案带来的有益技术效果：
本发明的多功能荧光纳米颗粒中的DPP类分子具有Hg2+识别能力，同时具有强的荧光发射以及双光子诱导荧光发射，而TPE类分子作为纳米颗粒的荧光内参，从而可以实现比率型Hg2+检测以及比率型双通道细胞成像。DPP类分子固有的双光子诱导荧光发射性能使纳米颗粒具备细胞双光子成像功能，利于获得更好的生物内部成像图片。
本发明的多功能荧光纳米颗粒中TPE类分子引入DPP类分子自组装形成胶束，TPE类分子起到维持纳米颗粒的稳定结构的作用，能保持纳米颗粒的稳定性。
本发明的多功能荧光纳米颗粒的制备方法简单、低成本，有利于大规模生产应用。
附图说明
图1为ODPP和OTPE的分子结构式；
图2为吡咯并吡咯二酮类化合物和四苯乙烯类化合物自组装成多功能荧光纳米颗粒的示意图。
图3为荧光纳米颗粒的粒径以及荧光图谱；
图4为荧光纳米颗粒在不同浓度Hg2+溶液中的荧光发射光谱图；
图5为荧光纳米颗粒用于海拉细胞的双通道荧光成像；
图6为荧光纳米颗粒用于海拉细胞的双光子荧光成像。
具体实施方式
为了更好地理解本发明专利的内容，下面通过具体的实例和图例来进一步说明本发明的技术方案。但这些实施实例并不限制本发明。
实施例1
多功能荧光纳米颗粒的制备。如图1所示，此实施例以两种烷氧基修饰的荧光分子(ODPP和OTPE)为原料来制多功能荧光纳米颗粒。在水中，按 ODPP:OTPE为1:4的比例加入两种荧光化合物，使其总浓度为50μM/L。利用两亲分子的自组装(图2)，超声0.5小时后制备成所需纳米颗粒。如图3所示，左图为通过激光动态光散射法测量的纳米颗粒水合粒径大小，右图为荧光发射图谱。
实施例2
荧光纳米颗粒对汞离子响应的荧光发射光谱如图4所示。在水溶液中，纳米颗粒在470nm和540nm均有发射峰，分别对应于TPE和DPP的荧光发射。随着汞离子的加入，TPE的荧光变化不大，而DPP的荧光强度逐渐减弱。利用 F540/F470对[Hg2+]作图，得到Hg2+检测限为13nM。
实施例3
荧光纳米颗粒在细胞双通道荧光成像方面的应用。在培养好的具有适宜细胞浓度的培养皿中，加入21μg/mL的纳米颗粒DPBS溶液孵育0.5小时。用DPBS 溶液洗去培养皿中的纳米颗粒后，采用共聚焦荧光显微镜对细胞进行成像。如图 5所示，纳米颗粒可以很好地进入海拉细胞，两种通道所得荧光图片均可清晰显示细胞质和细胞核。
实施例4
荧光纳米颗粒在细胞双光子荧光成像方面的应用。在培养好的具有适宜细胞浓度的培养皿中，加入21μg/mL的纳米颗粒DPBS溶液孵育0.5小时。用DPBS 溶液洗去培养皿中的复合颗粒后，采用双光子激光共聚焦显微镜对细胞进行成像 (770nm为激发波长)。如图6所示，纳米颗粒可以很好地进入海拉细胞，细胞质和细胞核清晰可见。
Claims (8)
1.一种基于吡咯并吡咯二酮类化合物和四苯乙烯类化合物的多功能有机荧光纳米颗粒，其特征在于：由吡咯并吡咯二酮类化合物和四苯乙烯类化合物通过分子自组装形成；
所述四苯乙烯类化合物具有式1结构：
所述吡咯并吡咯二酮类化合物具有式2结构：
其中，
R和R1独立选自亲水基团；
R2为噻吩基、呋喃基、吡咯基、吡啶基或芳基。
2.根据权利要求1所述的基于吡咯并吡咯二酮类化合物和四苯乙烯类荧光分子的多功能有机荧光纳米颗粒，其特征在于：吡咯并吡咯二酮类化合物与四苯乙烯类化合物的摩尔比为1:3～5。
3.根据权利要求1所述的基于吡咯并吡咯二酮类化合物和四苯乙烯类荧光分子的多功能有机荧光纳米颗粒，其特征在于：R和R1独立选自烷氧链、糖类基团或其他水溶性基团。
4.根据权利要求1～3任一项所述的基于吡咯并吡咯二酮类化合物和四苯乙烯类荧光分子的多功能有机荧光纳米颗粒，其特征在于：具有双荧光发射和双光子吸收功能。
5.权利要求1～4任一项所述的基于吡咯并吡咯二酮类化合物和四苯乙烯类化合物的多功能有机荧光纳米颗粒的制备方法，其特征在于：将吡咯并吡咯二酮类化合物和四苯乙烯类化合物加入水中，超声处理，即得。
6.根据权利要求5所述的基于吡咯并吡咯二酮类化合物和四苯乙烯类化合物的多功能有机荧光纳米颗粒的制备方法，其特征在于：吡咯并吡咯二酮类化合物和四苯乙烯类化合物在水中的总浓度为30～60μM/L。
7.权利要求1～4任一项所述基于吡咯并吡咯二酮类化合物和四苯乙烯类化合物的多功能有机荧光纳米颗粒的应用，其特征在于：应用于对Hg2+的比率型检测。
8.权利要求1～4任一项所述基于吡咯并吡咯二酮类化合物和四苯乙烯类化合物的多功能有机荧光纳米颗粒的应用，其特征在于：应用于细胞的双通道成像和双光子成像。
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