CN102676154B - 磷类酞菁及其衍生物作为荧光探针的应用 - Google Patents
磷类酞菁及其衍生物作为荧光探针的应用 Download PDFInfo
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Abstract
本发明公开了磷类酞菁及其衍生物作为荧光探针的应用。荧光成像效果显示，磷类酞菁及其衍生物有很特征的荧光峰，可以在任何情况下避免自发荧光的干扰。通过与[P(OH)2TBC]的比较，P(OH)2TBC(β-OiPr)4更易穿透细胞膜富集于线粒体部位，P(OH)2TBC(β-OiPr)4的标记效率明显高于转染的荧光标记效率。磷类酞菁及其衍生物是一类优异的荧光标记探针，可定位于细胞内线粒体而对线粒体进行荧光标记。
Description
技术领域
本发明涉及磷类酞菁及其衍生物作为荧光探针的应用。
背景技术
随着人类基因组计划的完成，对细胞亚区、亚结构的蛋白组成及其相互作用进行动力学分析成为研究的重点。利用荧光标记进行生物成像是进行这一研究的重要的手段。荧光探针技术在生物成像中起着重要的作用，可对研究对象进行示踪的作用。
由于荧光成像的检测灵敏度很大程度取决探针的发光强度和光化学稳定性，因此针对探针的研究开发已为荧光成像研究的核心领域。目前广泛使用的生物成像用荧光探针，按化学组成分主要有有机荧光染料等小分子发光材料、荧光蛋白、以及半导体量子点、碳纳米管等纳米发光材料。其中，使用最为广泛的是有机荧光染料、半导体量子点(QDs)、荧光蛋白(Chalfie M，Tu Y，Euskirchen G，Ward WW，Prasher DC.Greenfluorescent protein as a marker for gene expression.Science，1994，263(5148)：802-805.Glepmans BNG，Adams SR，Ellisman MH，Tsien RY.The fluorescent toolbox for assessing protein location and function.Science，2006，312(5771)：217-224.)。
在现代生物学中，活细胞单分子行为研究，以及活体动物成像已经成为荧光生物成像的前沿领域。无论是活体动物和活细胞，生物样品的自发荧光对标记分子信号的干扰非常严重。因此，开发光稳定性好、毒性低且有特异荧光特性的发光材料成为生物成像探针研究的新目标。
发明内容
本发明的目的是提供磷类酞菁及其衍生物作为荧光探针的应用。
本发明所述磷类酞菁化合物为磷四苯并三氮杂呵罗[P(OH)2TBC]，结构式见式I；其衍生物为四异丙氧基磷类酞菁[P(OH)2TBC(β-OiPr)4]，结构式见式II。上述化合物均可通过大环合成获得。
(式I) (式II)
本发明涉及的磷类酞菁及其衍生物具有生物相容的两亲性，及较好的光稳定性，具有成为荧光探针的基础。它们在活细胞内具有双荧光性质，可应用到生物成像领域，作为荧光探针用于线粒体内的荧光定位。
对磷类酞菁及其衍生物荧光成像效果显示，磷类酞菁及其衍生物有很特征的荧光峰，可以在任何情况下避免自发荧光的干扰。通过与[P(OH)2TBC]的比较，P(OH)2TBC(β-OiPr)4更易穿透细胞膜富集于线粒体部位，P(OH)2TBC(β-OiPr)4的标记效率明显高于转染的荧光标记效率。磷类酞菁及其衍生物是一类优异的荧光标记探针，将在线粒体荧光标记探针等相关活细胞成像及研究方面发挥重要作用。
附图说明
图1为P(OH)2TBC以10μg/ml加入Hela细胞培养12h后荧光显微镜照片；其中(a)为UV激发的荧光成像；(b)为蓝光激发的荧光成像；(c)为绿光激发的荧光成像；(d)明场成像。
图2为P(OH)2TBC以10μg/ml加入Hela细胞培养12h后，用405nm激光激发，扫描423nm-721nm范围内的荧光成像。
图3为P(OH)2TBC以10μg/ml加入Hela细胞培养12h后，用488nm激光激发，扫描500nm-721nm范围内的荧光成像。
图4为P(OH)2TBC以10μg/ml加入Hela细胞培养12h后，用543nm激光激发，扫描558nm-721nm范围内的荧光成像。
图5为线粒体标记EGFP(增强型绿色荧光蛋白)，P(OH)2TBC及其衍生物(P(OH)2TBC(β-OiPr)4)以10μg/ml加入Hela细胞培养12h后，用488nm激发，采集EGFP图像，543nm激光，采集P(OH)2TBC及其衍生物(P(OH)2TBC(β-OiPr)4)的离体荧光图像；(a)Hela细胞未加光敏剂；(b)加入P(OH)2TBC；(c)加入P(OH)2TBC(β-OiPr)4。
具体实施方式
下面通过具体实施例对本发明的用途做进一步说明。
下述实施例中所述实验方法，如无特殊说明，均为常规方法；所述试剂和生物材料，如无特殊说明，均可从商业途径获得。
实施例中所用的P(OH)2TBC和P(OH)2TBC(β-OiPr)4是参考下述文献中的合成路线制备的：L.Huang，P.Zhao，F.Zhang，Z.Li，C.-H.Tung.Synthesis and DualFluorescence Property of Novel Dihydroxy Phosphorus TetrabenzotriazacorroleDerivates.Proc.SPIE.2007，682714.。合成化合物经过质谱、元素分析、核磁进行确定，其结构为目标化合物。
实施例1、光敏剂的活细胞荧光成像观察
在体外细胞水平(in vitro)研究脂溶性P(OH)2TBC(β-OiPr)4和P(OH)2TBC对人***Hela细胞的成像效果，包括光敏剂加入后Hela细胞的荧光成像以及光敏剂的亚细胞定位情况。
将合成的光敏剂(P(OH)2TBC或P(OH)2TBC(β-OiPr)4)加入到HeLa细胞中，避光培养12小时，使用Olympus IX71(日本)倒置荧光显微镜，用X-Cite金属卤化物灯激发，通过UV/BLU/GRE滤色片分别进行观测。使用物镜为LUCPlanFLN的20X物镜，N.A.为0.45。结果如图1所示，其中(a)为UV激发的荧光成像；(b)为蓝光激发的荧光成像；(c)为绿光激发的荧光成像；(d)明场成像。
荧光显微镜下，观察到光敏剂被吸收到细胞内，且分别发出蓝色、绿色及红色荧光，如图1。根据磷类酞菁在溶液中的荧光光谱显示，当光敏剂被短波长的光激发时荧光光谱上会出两个荧光峰。推测其中靠近短波方向的荧光峰在细胞内环境下为蓝绿色区域的荧光。
实施例2、光敏剂荧光成像的激光共聚焦光谱研究
光敏剂活细胞荧光成像情况进一步通过共聚焦显微镜观察，使用的激光共聚焦显微镜型号为Zeiss LSM710(德国)。采用韩国LCI公司的Chamlide TC显微活细胞培养***，保持Hela细胞在37℃、体积分数为5％的CO2、饱和湿度条件下进行观察。
由于磷类酞菁(P(OH)2TBC)及其衍生物(P(OH)2TBC(β-OiPr)4)在细胞内的荧光光谱未知，因此固定激发波长采用全光谱扫描方法进行检测。加入磷类酞菁避光培养12h，用固体激光器405nm激光为激发光，在激光共聚焦显微镜下进行λ扫描，得到的荧光成像效果，如图2所示。可以看出当激发光为405nm时，磷类酞菁在Hela细胞内的荧光谱峰为442nm-548nm。
当激发光为488nm时，如图3所示，在激光共聚焦显微镜下进行λ扫描，得到磷类酞菁在Hela细胞内的荧光谱峰为615nm-673nm。当激发光为543nm光时，对558nm-721nm范围进行检测，得到磷类酞菁在Hela细胞内的荧光谱峰范围为558nm-634nm，如图4。激发光改变时，荧光发射范围也会有所改变，但无论是488nm还是543nm的光激发出的磷类酞菁在Hela细胞内的荧光都属于长波长红光范围内的荧光，为磷类酞菁对应的S1态荧光。而只有在405nm或更短的波长下激发的才是S2态荧光，被Hela细胞吸收后为蓝绿色荧光。
实施例3、光敏剂在活细胞内的线粒体定位
磷类酞菁被Hela细胞吸收后的荧光发射谱确定后，进一步对其定位进行观察。加入磷类酞菁避光培养12h后在Hela细胞内磷类酞菁的荧光成像呈线状，也有粒状或短线状，直径一般在0.5～1.0μm。推测为线粒体定位，进而采用电转法标记Hela细胞的线粒体，采用的标记为EGFP。观测时选择两通道扫描方法，共聚焦上选择EGFP和Rhodamin的染料范围，即488nm激发，492nm-525nm采集EGFP的图像；543nm激发565nm-685nm采集磷类酞菁及其衍生物光敏剂(PS)的荧光图像，如图5所示，其中(a)Hela细胞未加光敏剂；(b)Hela细胞加入P(OH)2TBC；(c)Hela细胞加入P(OH)2TBC(β-OiPr)4。
通过比较线粒体荧光和磷类酞菁及其衍生物在细胞内的荧光，可以看出两者有明显的共定位。在P(OH)2TBC(β-OiPr)4的图像中转染的荧光标记效率明显低于磷类酞菁衍生物的标记效率，Hela细胞在未加光敏剂时无红色荧光，在加入光敏剂时细胞都被标记了线粒体红色荧光。P(OH)2TBC(β-OiPr)4更易穿透细胞膜富集于线粒体部位，磷类酞菁衍生物的标记效率明显高于转染的荧光标记效率。是一类优异的荧光标记探针。
Claims (2)
1.式Ⅰ所示的磷四苯并三氮杂呵罗和/或式Ⅱ所示的四异丙氧基磷类酞菁作为荧光探针的应用；所述荧光探针用于定位标记细胞内的线粒体；
2.式Ⅰ所示的磷四苯并三氮杂呵罗和/或式Ⅱ所示的四异丙氧基磷类酞菁在制备荧光探针中的应用；所述荧光探针用于定位标记细胞内的线粒体；
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