CN114790388B - 一种化合物作为近红外荧光探针在脂滴成像中的应用 - Google Patents
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Abstract
本发明公开了一种化合物作为近红外荧光探针在脂滴成像中的应用，所述化合物的结构式为：
该化合物作为探针对环境粘度变化比较敏感，有优异的亮度和光稳定性，能够快速透过细胞并富集于脂滴中，实现脂滴的免洗荧光成像，借助共聚焦荧光显微镜实现了细胞内脂滴的荧光成像，可对斑马鱼体内的脂滴动态分布进行监测，在细胞生物学研究中具有广阔的应用前景。
Description
技术领域
本发明属于分析化学技术领域，具体涉及一种化合物作为近红外荧光探针在脂滴成像中的应用。
背景技术
脂滴(Lipid droplets,LDs)是细胞内中性脂肪的主要存储部位，大小差异明显，直径从40nm至100μm不等，最外面被表面装饰有特定蛋白质的磷脂单分子层包裹着，内部主要是由纯有机中性脂核(即三酰甘油和甾醇酯)组成。脂滴在脂类代谢与存储、膜转运、蛋白降解以及信号传导过程中起着重要的作用。
近年来，荧光成像技术已经成为在生命系统背景下监测目标和生物过程的最强大的技术之一。然而，大多数荧光探针在紫外-可见光(UV/Vis)范围内具有吸收和发射，此波长区域的光很容易被生物分子(如水和血红蛋白)吸收，并且很容易分散，限制了对组织的渗透能力。相比之下，荧光探针在近红外(NIR)区域(600～900nm)的吸收和发射有利于活体生物成像，并且对生物样品的光损伤最小，能穿透深层组织。目前，已报道的用于检测脂滴的荧光探针大多集中在紫外-可见光(UV/Vis)范围内，不利于研究生物体内脂滴的生物过程。因此，构建结构新颖的具有大斯托克斯位移的近红外荧光探针对可视化研究脂滴的生物学功能方面具有重要意义。
发明内容
本发明公开了一种化合物作为近红外荧光探针在脂滴成像中的应用，所述化合物的结构式如下：
该化合物作为荧光探针能够快速透过细胞并富集于脂滴中，借助共聚焦荧光显微镜实现了细胞内脂滴的荧光成像，而且可对斑马鱼体内的脂滴动态分布进行监测，具有高亮度、低成像背景、高光稳定性等优点。
本发明的有益效果如下：
本发明所述化合物的分子结构简单，合成原料低价、方法简单，具有聚集诱导发光的特性，即在溶液中不发光、在聚集态下荧光增强的特性，其作为近红外荧光探针对环境粘度变化极其敏感，探针在甲醇中荧光量子产率小于0.01，而在甘油中荧光量子产率可达到0.30，使探针具有很高的亮度，并且有效地降低了成像时的背景干扰，增加了探针的光稳定性。该探针能够快速透过细胞并富集于脂滴中，可以实现对细胞中脂滴的精准定位和特异性标记，可用于细胞或组织中脂滴的荧光成像，实现快速、高灵敏度的检测细胞内的脂滴，而且可对斑马鱼体内的脂滴动态分布进行监测，实现脂滴动态过程的跟踪及各种脂质的成像、传感、检测等研究。
附图说明
图1是CMDP-NO2在水溶液中归一化荧光激发与发射谱图，横坐标为波长，纵坐标为归一化的荧光强度与吸收强度，CMDP-NO2的浓度为10μM。
图2是CMDP-NO2在不同粘度体系中的荧光强度，CMDP-NO2的浓度为10μM。
图3是CMDP-NO2与BODIPY493/503对HepG2细胞内脂滴共定位实验的共聚焦显微镜照片。
图4是CMDP-NO2快速成像的共聚焦显微镜照片。
图5是CMDP-NO2免洗成像的共聚焦显微镜照片。
图6是CMDP-NO2对斑马鱼体内脂滴的共聚焦显微镜照片。
具体实施方式
下面结合附图和实施例对本发明进一步详细说明，但本发明的保护范围不仅限于这些实施例。
实施例1
1、目标化合物的合成
(1)将三氯氧磷(6.0mL，0.06mol)缓慢滴加到盛有10.0mL DMF的圆底烧瓶中，混合物在0℃下搅拌反应30min，然后将化合物1(1.0g，6mmol)溶解于5.0mL DMF中，并缓慢滴加到烧瓶中，此混合物在90℃下搅拌反应5h，反应完全后，将混合物倒入50.0mL冰水中，过滤收集析出的沉淀，并用冰水洗涤、干燥，即得褐色固体化合物2(953.0mg，产率72％)。1H NMR(400MHz,DMSO-d6)δ10.24-10.15(s,1H),7.79-7.67(s,1H),6.98-6.86(s,2H),3.85-3.80(s,3H),2.83-2.76(d,J＝7.8,2H),2.53-2.48(s,2H)；13C NMR(101MHz,DMSO-d6)δ190.19,162.50,145.16,141.81,130.08,128.46,124.45,114.20,114.04,56.04,27.09,21.75.HRMS(ESI):m/z C12H11ClO2[M+Na]+理论值245.0345,实测值245.0331。
(2)将化合物2(20.0mg，0.09mmol)和化合物3(18.0mg，0.10mmol)加入到5.0mL甲醇中，先在70℃下搅拌反应30min，然后加入10.0μL哌啶再反应2h，等混合物缓慢冷却至室温，抽滤得到粗品，用冷乙醇洗涤粗品3次，最终得到红色固体化合物4(24.0mg，产率81％)，记为CMDP-NO2。1H NMR(400MHz,DMSO-d6)δ8.36-8.24(s,2H),8.13-8.05(s,1H),7.98-7.88(s,2H),7.69-7.54(s,1H),6.96-6.86(s,2H),3.84-3.79(s,3H),3.11-2.98(s,2H),2.97-2.84(s,2H).13C NMR(101MHz,DMSO-d6)δ161.75,147.80,143.40,141.13,140.46,138.34,128.11,127.45,125.06,125.01,117.65,108.80.HRMS(ESI):m/z C20H15ClN2O3[M+Na]+理论值389.0669,实测值389.0633。
2、CMDP-NO2在甘油中的光谱测试
将CMDP-NO2溶解于乙腈中，配制成1mM CMDP-NO2母液，取20μLCMDP-NO2母液加入4mL甘油中，配制成10μM的CMDP-NO2测试液，并进行紫外吸收光谱和荧光发射光谱的测试。CMDP-NO2在甘油中的归一化紫外吸收光谱和荧光发射光谱如图1所示，其中CMDP-NO2浓度为10μM，CMDP-NO2在甘油中量子产率达到0.30，具有较高的亮度。
3、CMDP-NO2在甲醇/甘油不同粘度体系中的光谱测试
取20μL CMDP-NO2母液，加入不同体积比的甲醇/甘油体系中，配制成10μM的CMDP-NO2测试液，并进行荧光发射光谱的测试。CMDP-NO2在甲醇/甘油中的荧光发射光谱如图2所示，其中CMDP-NO2浓度为10μM，由图2可见，CMDP-NO2的荧光强度随体系粘度的增加而增强。
4、CMDP-NO2作为近红外荧光探针在脂滴成像中的应用
将HepG2细胞与5μM CMDP-NO2和500nM BODIPY493/503一起孵育15min，使用共聚焦显微镜对细胞进行成像实验。如图3所示，CMDP-NO2在HepG2细胞中成像亮度高，成像背景低，并与BODIPY493/503产生的荧光信号重叠良好，皮尔逊相关系数为0.91。证明CMDP-NO2对细胞内的脂滴具有良好的靶向能力。
取0.5μL 1mM CMDP-NO2母液溶于1mL细胞培养液中，分别在0、1、3、5min使用共聚焦显微镜对同一视野下的细胞进行成像。如图4所示，CMDP-NO2对活细胞脂滴快速成像。
5、CMDP-NO2对活细胞脂滴免洗成像
HepG2细胞与5μM CMDP-NO2孵育15min，然后不需要PBS缓冲液清洗细胞，立即使用共聚焦显微镜对细胞进行成像实验。如图5所示，CMDP-NO2在细胞内发出强烈的荧光信号且没有明显的背景干扰。
6、CMDP-NO2对斑马鱼体内脂滴的动态分布监测
将斑马鱼与5μM CMDP-NO2一起孵育15min，如图6所示，可以观察到斑马鱼体内脂滴含量较高的腹部和头部发出强烈的荧光信号。成像过程中，CMDP-NO2成像亮度高、背景低，且成像过程中亮度无明显下降，证明CMDP-NO2有很高的光稳定性，可以实现对斑马鱼体内脂滴的分布进行实时跟踪成像。
Claims (3)
1.下式化合物作为近红外荧光探针在脂滴成像中的应用：
2.根据权利要求1所述的化合物作为近红外荧光探针在脂滴成像中的应用，其特征在于：所述化合物作为近红外荧光探针用于细胞内脂滴的特异性标记并荧光成像。
3.根据权利要求1所述的化合物作为近红外荧光探针在脂滴成像中的应用，其特征在于：所述化合物作为近红外荧光探针用于斑马鱼体内脂滴的动态分布监测。
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