CN109400563A - 一种次氯酸荧光探针及其制备方法和应用 - Google Patents

一种次氯酸荧光探针及其制备方法和应用 Download PDF

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CN109400563A
CN109400563A CN201811072605.6A CN201811072605A CN109400563A CN 109400563 A CN109400563 A CN 109400563A CN 201811072605 A CN201811072605 A CN 201811072605A CN 109400563 A CN109400563 A CN 109400563A
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王建勇
曲建波
张海涛
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Shandong Jiqing Technology Service Co ltd
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Abstract

一种次氯酸荧光探针及其制备方法和应用，该探针的分子式为：C26H24N4O6S；本发明设计的次氯酸荧光探针，合成步骤简单、原料易得、合成路线成熟，能够对细胞中的次氯酸进行快速准确检测并可以进行荧光成像研究。

Description

一种次氯酸荧光探针及其制备方法和应用
技术领域
本发明涉及一种专一性检测次氯酸的有机荧光探针及制备方法和应用，属于有机小分子荧光探针领域。
背景技术
在动物体内，活性氧(ROS)小分子在很多生理和病理过程中起着很关键的作用。生物体内的活性氧小分子主要包括两类：一类是含氧自由基(如：羟基自由基和超氧阴离子自由基等)；一类是非自由基(如：次氯酸)。在生物体内，各种活性氧物种主要是由酶促和非酶促反应产生的。现代的医学研究证明，生物体内在氧化应激、炎症等生理和病理情况下产生的活性氧物种，与一些重大疾病有着密切的关系。次氯酸作为非常重要的活性小分子，在日常生活中被广泛用作漂白剂、除臭剂和消毒剂。在生物细胞(如嗜中性白细胞)内，次氯酸由次氯酸和氯离子在髓过氧化物酶(MPO)的催化作用下产生。研究表明，次氯酸在维持细胞内的氧化还原平衡状态起着非常重要的作用，一旦细胞中次氯酸的浓度发生异常，就会引起一些疾病，如：风湿性关节炎、心血管疾病和癌症在内的多种疾病。因此，发展一种方法用于检测生物体系中次氯酸浓度是非常重要的。
然而目前对次氯酸检测的探针中存在识别位点单一问题，一般次氯酸的检测位点有硫醚键、羟胺、苯胺基等，因此，发展新的识别位点应用于次氯酸的检测尤为重要，并且通过新识别位点的改变可以实现次氯酸的快速检测。
发明内容
本发明要解决的技术问题是针对目前次氯酸荧光探针所面临的问题，提供一种次氯酸荧光探针，该荧光探针选择性好，响应速度快；该荧光探针可作为显示水溶液中和生物细胞内次氯酸分子存在的专一性指示剂，可进行实时定性的目视比色法检测；
本发明还提供了一种次氯酸荧光探针的制备方法，该方法合成步骤简单，原料易得，且后处理过程相对简单；
本发明还提供了一种上述荧光探针的应用。
本发明采用以下技术方案，通过有机分子设计和识别位点的改进，合成出一种可以快速检测次氯酸的有机小分子荧光探针。
本发明的所设计的有机小分子荧光探针的分子结构式如下:
探针CoPh-ClO的合成路线如下：
将化合物CoPh(C20H19NO3，2mmol，624mg)(是否可以提供相关分子式)和化合物1(C6H7N3O4S，2mmol，434mg)加入含有5mL乙醇的反应瓶中，点板检测反应至原料消失，萃取，浓缩，柱层析分离得到探针CoPh-ClO。
本发明次氯酸荧光探针的用途：该荧光探针可以应用于活动物体系中HClO的含量传感检测；所述的传感检测包含荧光检测和细胞成像。
本发明采用上述技术方案具有以下优点：
(1)探针的合成步骤简单，原料易得，且后处理过程相对简单；
(2)本发明所采用的次氯酸识别位点未被使用过，并且次氯酸分子探针的选择性好，响应速度快；
(3)基于其特异性和显著的荧光特性变化，该试剂可作为显示水溶液中和生物细胞内次氯酸分子存在的专一性指示剂，可进行实时定性的目视比色法检测；
(4)故而，本发明是一种简单，快速，灵敏的次氯酸分子特异性检测试剂，在生物分子检测领域具有广阔的应用前景。
附图说明
图1是实施例一中探针CoPh-ClO的1H NMR图谱；
图2是探针CoPh-ClO随HClO的加入荧光强度的变化情况；
图3是探针CoPh-ClO随时间变化荧光强度变化情况；
图4是探针CoPh-ClO选择性柱状图数据；
图5是探针CoPh-ClO应用于细胞中外源性HClO的荧光成像；
图6是探针CoPh-ClO应用于细胞中内源性HClO的荧光成像。
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，实施例中化合物的号码对于上述方案中化合物的号码，CoPh-ClO代表次氯酸荧光探针。
实施例1，探针化合物CoPh-ClO的合成路线如下：
化合物CoPh-ClO的合成：
将化合物CoPh(分子式为C20H19NO3，2mmol，624mg)和化合物1(分子式为C6H7N3O4S，2mmol，434mg)加入含有5mL乙醇的反应瓶中，点板检测反应至原料消失，萃取，浓缩，柱层析分离得到探针CoPh-ClO。产率92％。1H NMR(400MHz,CDCl3)δ11.92(s,1H),8.45(d,J＝8.8Hz,2H),8.17(s,1H),8.15(s,2H),7.97(s,1H),7.76(d,J＝8.4Hz,2H),7.63(d,J＝8.4Hz,2H),7.52(d,J＝8.8Hz,1H),6.75(dd,J＝9.2,6.8Hz,1H),6.56(d,J＝2.0Hz,1H),3.48-3.43(m,4H),1.90-1.12(m,6H).该探针的1H NMR图谱见图1。
探针化合物CoPh-ClO的分子式为：C26H24N4O6S。
实施例2，取实施例1制备的探针CoPh-ClO溶于二甲基亚砜(DMSO)中，制成1mmol/L储备液。在含有5％DMSO的PBS缓冲溶液(0.1mol/L，pH＝7.5)中加入15μL储备液，加入不同当量(0-20equiv)的HClO标准溶液，终体积为3mL，测量其荧光性质(λex＝420nm，光栅宽度为5nm，5nm)。如图2所示，探针化合物CoPh-ClO荧光探针随HCLO加入当量的增加荧光谱图的变化，由图2可见，随着HClO加入当量的增加荧光逐渐增强。
实施例3，从实施例2中荧光探针储备液中取出15μL加入含有5％DMSO的PBS缓冲溶液(0.1mol/L，pH＝7.5)中，加入HClO(20equiv)标准溶液最终体积为3mL，测量其荧光性质。荧光光谱如图3所示，探针CoPh-ClO对随时间变化的荧光谱图的变化，由图3可见，加入探针CoPh-ClO后，直接加入HClO，荧光强度增加迅速达到最大，并保持稳定荧光强度10分钟，实现了HClO的检测。
实施例4，从实施例2中荧光探针储备液中取出30μL加入到5mL的离心管当中，分别加入等摩尔量的竞争分子标准溶液，其中一个加入等摩尔量的HClO标准溶液，测试体系溶液体积为3mL，20min后检测溶液的荧光发射光谱变化，化合物CoPh-ClO荧光探针对不同离子的选择性由图4可以发现，其他干扰离子对化合物CoPh-ClO的荧光几乎没有影响，而HClO溶液的加入使化合物CoPh-ClO的荧光显著增强。
在含有DMSO(5％)的PBS溶剂中，探针CoPh-ClO(10μM)对不同离子和分子的选择性柱状谱图：1:None；2:GSH；3:Cys；4:Hcy；5:F-；6:Cl-；7:Br-；8:·OH；9:ONOO-；10:DTBP；11:TBHP；12:NO；13:H2O2；14:NO2 -；15:Co2+；16:Cu2+；17:Ni+；18:ClO-。
实施例5，CoPh-ClO荧光探针对细胞中HClO荧光成像。
我们将本发明探针应用于HeLa细胞中HClO的检测进行荧光成像应用，如图5所示，具体操作步骤如下：
a)将20μM探针DMF溶液加入到育有HeLa细胞的培养液中在二氧化碳培养箱中培养0.5h，明场成像，可以看到细胞大致的轮廓；
b)将a)用405nm激光激发得到成像图；
c)将a)和b)图成像叠加；
d)将20μM探针DMF溶液加入到育有HeLa细胞的培养液中在二氧化碳培养箱中培养0.5h，加入HClO后，明场成像，可以看到细胞大致的轮廓；
e)将d)用405nm激光激发得到成像图；
f)将d)和e)图成像叠加。
说明此荧光探针实现细胞中HClO的检测。
实施例6，探针CoPh-ClO针对细胞内源性HClO的细胞成像。
我们将本发明探针应用与Raw 246.7细胞中对内源性的HClO进行荧光成像应用。如图6所示，具体操作步骤如下：
a)将20μM探针DMF溶液加入到育有Raw 264.7细胞的培养液中在二氧化碳培养箱中培养0.5h，明场成像，可以看到细胞大致的轮廓；
b)将a)用蓝光进行激发得到成像图；用405nm激光激发观察在未加入探针前的荧光成像情况，此时观察不到荧光发射；
c)将a)和b)图成像叠加；
d)先将Raw 264.7细胞加入LPS(2μg/mL)和PMA(2μg/mL)孵育2h，再将10μM探针DMF溶液加入到细胞的培养液中，在二氧化碳培养箱中培养0.5h后得到的明场成像，可以看到细胞大致的轮廓；
e)用蓝光进行激发得到成像图；向体系中加入探针CoPh-ClO(20μM)的DMF溶液，等待30min后用405nm激光激发可以观察到有蓝光发出，说明此荧光探针可以对内源性的HClO进行荧光成像；
f)将d)和e)图成像叠加。

Claims (5)

1.一种次氯酸荧光探针，其特征在于：该探针的分子式为：C26H24N4O6S。
2.根据权利要求1所述的次氯酸荧光探针，其特征在于：该探针结构如下：
3.一种如权利要求1所述的次氯酸荧光探针的制备方法，其特征在于：按照以下步骤进行：将化合物CoPh，化合物CoPh的分子式为C20H19NO3和化合物4，化合物4的分子式为C6H7N3O4S，加入乙醇的反应瓶中，点板检测反应至原料消失，萃取，浓缩，柱层析分离得到探针CoPh-ClO。
4.一种如权利要求1所述的次氯酸荧光探针的应用，其特征在于：该荧光探针应用于生物细胞体系中HClO的含量传感检测。
5.根据权利要求4所述的次氯酸荧光探针的应用，其特征在于：所述的传感检测包含荧光检测和细胞成像检测。
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