CN110156713A - 一种检测脂滴的荧光探针及其制备方法和应用 - Google Patents

一种检测脂滴的荧光探针及其制备方法和应用 Download PDF

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CN110156713A
CN110156713A CN201910396073.XA CN201910396073A CN110156713A CN 110156713 A CN110156713 A CN 110156713A CN 201910396073 A CN201910396073 A CN 201910396073A CN 110156713 A CN110156713 A CN 110156713A
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林伟英
于法祺
景新颖
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Abstract

本发明提供一种检测生物细胞内脂滴的荧光探针，其化学结构式为：。该荧光探针是基于生物相容性的聚乙二醇的荧光探针，可以很好地定位细胞中的脂滴，响应速度快，抗干扰能力强。该荧光探针由聚乙二醇与4‑氯‑7‑硝基苯并‑2‑氧杂‑1,3‑二唑在室温下反应制得，该探针合成步骤简单，易提纯。

Description

一种检测脂滴的荧光探针及其制备方法和应用
技术领域
本发明属于分析化学技术领域，具体涉及一种基于聚乙二醇的检测细胞内脂滴的荧光探针及其应用。
背景技术
脂滴是一种呈球状的细胞器，其核心组成是中性脂，包括甘油三酯和胆固醇酯。脂滴主要功能是调节细胞的能量动态平衡，在白色脂肪组织里，脂滴主要是储存甘油三酯，储存能量；在棕色脂肪组织里，脂滴和线粒体紧密联系，分解甘油三酯，提供细胞和生物有机体能量。脂滴是细胞内最疏水的细胞器，广泛存在于动植物、细菌和酵母细胞中；它的大小也有很大差别，直径从40 nm到100 μm不等。研究表明脂滴不只是能量的储存器，而是一个复杂的多功能的细胞器，它在膜合成、蛋白质降解和信号转导等生理过程中发挥着重要作用。脂滴的异常与多种疾病有关，包括脂肪肝、II型糖尿病、高血脂症，甚至阿尔茨海默症。最近的研究表明，脂滴的功能障碍也与癌症的发展有关。因此，为了解脂滴在上述疾病中发生发展的作用，设计实用的脂滴标记探针是十分必要的。荧光生物探针对目标分析物具有高灵敏度、实时和原位检测等优点，已被广泛应用于生物医学领域。许多荧光染料被用于对脂滴的成像，虽然它们呈现出很好地成像效果，但是仍然需要改进。比如，尼罗红作为第一个商业化的荧光染料，在成像过程中不稳定，容易被漂白。
现有的脂滴探针多是小分子的荧光探针，它们光稳定性不好并且容易被漂白，而基于聚合物的脂滴探针报道比较少，尤其是以生物相容性的聚合物为基体的脂滴探针的报道更少。
发明内容
针对目前脂滴探针存在的问题，本发明提供一种检测细胞内脂滴的荧光探针，响应速度快、抗干扰能力强。
本发明的另一目的是提供一种上述荧光探针在检测生物细胞内脂滴的应用。
为实现上述目的，本发明采用如下技术方案。
一种检测生物细胞内脂滴的荧光探针，简称为PEG-NBD，其化学结构式为：
；
其中，n=4-44。
一种上述荧光探针的制备方法，包括以下步骤：
。
在氮气保护下，聚乙二醇与4-氯-7-硝基苯并-2-氧杂-1,3-二唑，在二氯甲烷和三乙胺中反应，分离提纯得荧光探针PEG-NBD。
所述聚乙二醇的平均分子量为200-2000。
所述聚乙二醇与4-氯-7-硝基苯并-2-氧杂-1,3-二唑的物质的量比为1:2.5。反应时间为24 h。所述分离提纯步骤为将反应液旋蒸，以石油醚/二氯（V/V）=2 : 1为洗脱剂，经硅胶柱提纯得荧光探针PEG-NBD。
一种上述荧光探针在制备检测细胞或生物体中脂滴试剂中的应用。
本发明具有以下优点：
本发明提供的脂滴荧光探针是基于聚乙二醇的荧光探针，目前针对脂滴的聚合物基荧光探针报道的并不多，尤其是基于生物相容性的聚乙二醇的荧光探针更少。该探针合成步骤简单，易提纯，响应速度快，抗干扰能力强，光稳定性好。
附图说明
图1是探针PEG-NBD的1H NMR图谱；
图2是探针PEG-NBD在水相中的选择性，其中激发波长为470 nm；探针终浓度为5 µg/mL，分析物的浓度为100 µM；
图3是探针PEG-NBD在不同极性溶剂中的荧光光谱，其中激发波长为460 nm，探针终浓度为5 µg/mL；
图4是探针PEG-NBD在HepG2和HeLa细胞中的生物成像。其中激发波长为405 nm，探针的终浓度5 µg/mL；
图5是探针PEG-NBD和商业化染料Nile Red在HeLa细胞中的共定位成像。其中，探针激发波长为405 nm，发射波长为500-550 nm，探针的终浓度5 µg/mL；商业化染料的激发波长为561 nm，发射波长为570-620 nm，染料浓度为2 µM；
图6是探针PEG-NBD在HeLa细胞中的光稳定性测试。其中，激发波长为405 nm，持续照射时间为15 min，探针的终浓度5 µg/mL。
具体实施方式
下面结合实施例和附图对本发明做进一步说明，但本发明不受下述实施例的限制。
实施例1 荧光探针PEG-NBD的合成
在25 mL茄形烧瓶中，加入0.2 g PEG-200和10 mL二氯甲烷，再加入0.5 g 4-氯-7-硝基苯并-2-氧杂-1,3-二唑（NBD-Cl），最后加入几滴三乙胺（TEA），在氮气保护下常温反应24小时。将得到的粗产物旋蒸，以石油醚/二氯（V/V）=2:1为洗脱剂，经过硅胶柱提纯得到产物PEG-NBD。其1H NMR图谱如图1。
实施例2 荧光探针PEG-NBD的选择性
配制5 mL浓度为100 mM的氨基酸、金属离子、活性氧的PBS（pH=7.4）水溶液及浓度为1mM的实施例1所得荧光探针PEG-NBD母液备用。
加入20 μL探针母液、200 μL DMSO和100当量的各氨基酸、离子、硫醇及活性氧物质，用磷酸缓冲液PBS定容至2 mL，摇匀后进行荧光检测（λex = 470 nm），建立荧光强度与各离子（氨基酸或活性氧）的柱状图，结果如图2，1-28加入的检测物分别为PBS溶液、精氨酸、丝氨酸、丙氨酸、天冬氨酸、谷氨酸、组氨酸、异亮氨酸、苏氨酸、谷氨酰胺、N-乙酰-L-半胱氨酸、N-乙酰甘氨酸、氯化铝、氯化钙、氯化铜、硫酸亚铁、碘化钾、氯化镁、硫化钠、亚硫酸钠、溴化钠、次氯酸钠、亚硝酸钠、氯化锌、半胱氨酸、同型半胱氨酸、谷胱甘肽和过氧化氢。由图2可以发现，常规的氨基酸（离子、硫醇或活性氧）对聚合物PEG-NBD的荧光几乎没有影响。
实施例3 荧光探针PEG-NBD在不同极性溶剂中的荧光光谱
选取八种不同极性的溶剂，包括水、甲醇、乙腈、二甲基亚砜、二氯甲烷、四氢呋喃、二氧六环和甲苯；配制5 mL浓度为1 mM的实施例1所得荧光探针PEG-NBD母液作为备用。配制探针终浓度为5 µg/mL，分别加入不同极性的溶剂中，并进行荧光检测（λex = 460 nm），其荧光谱图如图3所示。由图3可知，溶液极性不同，荧光强度差别很大，极性越大荧光越低，说明荧光探针PEG-NBD具有极性响应。
实施例4 荧光探针PEG-NBD在癌细胞中对脂滴的成像测试
配置1mL终浓度为5 µg/mL的实施例1所得荧光探针PBS溶液，然后加入到HeLa和HepG2细胞中孵育30 min成像，激发波长为405 nm，发射波长为500-550 nm，如图4所示。由图4可知，HeLa细胞中出现了绿色的点状荧光信号，说明探针很容易进入到极性低的细胞中。
实施例5 荧光探针PEG-NBD和染料Nile Red的共定位测试
配置1mL浓度为2 µM的Nile Red染料的PBS溶液，加入到HeLa细胞中孵育，再加入10 µL探针的母液（1 mM）。探针激发波长为405 nm, 发射波长为500-550 nm；商业化染料的激发波长为561 nm, 发射波长为570-620 nm，如图5所示。由图5可知，荧光探针PEG-NBD与商业化染料对脂滴的孵染重合性很好，共定位系数可以达到0.97。
实施例6 荧光探针PEG-NBD在HeLa细胞中的光稳定性测试
配置1mL终浓度为5 µg/mL的实施例1所得荧光探针PBS溶液，然后加入到HeLa细胞中孵育30 min成像，其中激发波长为405 nm，持续照射时间为15 min，如图6所示。由图6可知，持续照射15 min，探针PEG-NBD的荧光信号没有明显的变化，说明其光稳定性较好。

Claims (5)

1.一种检测生物细胞内脂滴的荧光探针，其化学结构式为：
；
其中，n=4-44。
2.一种如权利要求1所述的荧光探针的制备方法，其特征在于，包括以下步骤：
在氮气保护下，聚乙二醇与4-氯-7-硝基苯并-2-氧杂-1,3-二唑，在二氯甲烷和三乙胺中反应，分离提纯得荧光探针；
所述聚乙二醇的平均分子量为200-2000。
3.根据权利要求2所述的所述制备方法，其特征在于，聚乙二醇与4-氯-7-硝基苯并-2-氧杂-1,3-二唑的物质的量比为1:2.5。
4. 根据权利要求2所述的所述制备方法，其特征在于，所述分离提纯步骤为将反应液旋蒸，以石油醚/二氯=2:1 V/V为洗脱剂，经硅胶柱提纯得荧光探针。
5.一种如权利要求1所述的荧光探针在制备检测细胞或生物体中脂滴试剂中的应用。
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Cited By (5)

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CN110927137A (zh) * 2019-12-31 2020-03-27 吉林大学 一种基于单苯环骨架的细胞脂滴荧光成像探针及其应用
CN112174946A (zh) * 2020-11-05 2021-01-05 四川大学华西医院 一种脂滴荧光探针及其合成方法和应用
CN113087703A (zh) * 2021-03-03 2021-07-09 四川大学华西医院 一种能特异性标记脂滴的光敏剂及其制备方法
CN113358616A (zh) * 2021-06-01 2021-09-07 吉林大学 基于双噻吩并苯衍生物的细胞脂滴荧光成像探针及其应用
CN113582940A (zh) * 2021-09-07 2021-11-02 四川大学华西医院 一类脂滴特异性荧光探针及其合成方法

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