CN105693600A - 一种识别半胱氨酸的小分子荧光探针及其制备方法和应用 - Google Patents

一种识别半胱氨酸的小分子荧光探针及其制备方法和应用 Download PDF

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CN105693600A
CN105693600A CN201610171754.2A CN201610171754A CN105693600A CN 105693600 A CN105693600 A CN 105693600A CN 201610171754 A CN201610171754 A CN 201610171754A CN 105693600 A CN105693600 A CN 105693600A
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林伟英
王建勇
刘展榕
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Abstract

本发明公开了一种识别半胱氨酸的小分子荧光探针及其制备方法和应用，属于有机小分子荧光探针领域。该探针得制备只需要一步即可完成，合成方法简单，实现了Cys分子探针的选择性快速检测，并且选择性好，抗其他分子干扰能力强。可以应用于水环境和生物细胞体系中Cys的传感检测，如荧光检测和细胞成像检测。因而本发明是一种简单，快速，灵敏的Cys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。

Description

一种识别半胱氨酸的小分子荧光探针及其制备方法和应用
技术领域
本发明涉及一种快速检测半胱氨酸的小分子荧光探针及其制备方法和应用，属于有机小分子荧光探针领域。
背景技术
半胱氨酸（Cys）是谷胱甘肽的前体，在调节人的生理机能方面有着非常关键的生物化学作用，包括：生物催化、蛋白质转录后修饰和针对外源物质进行解毒作用等。体内Cys的缺乏可能会导致许多疾病产生，例如：当体内缺乏Cys时，可能会导致儿童发育缓慢、头发褪色、水肿、疲乏、肝脏受到损伤、肌无力、肥胖以及皮肤病等。因此，该类小分子在体内起着非常重要的作用；对生物体内的Cys进行检测具有非常重要的科学意义。
传统的Cys检测方法主要有：高效液相法、电泳法、电化学分析法、紫外可见光谱法、傅立叶转换红外光谱法、质谱分析法等。近年来随着有机小分子荧光探针的不断发展逐渐显现出特有的性质，比如：灵敏度高、操作简便、重现性好、膜透性好、原位检测等众多优点，使得有机小分子荧光探针日益成为现代生命科学及疾病诊断等领域不可缺少的研究手段，已被越来越多地应用于多种复杂生物、环境样品中的Cys的检测及成像分析。因此，发展新型的有机小分子荧光探针应用于Cys的检测中具有较强的应用价值。
在生物体内，存在着大量的不同类型的干扰离子或分子，因此，在其他存在的情况下，专一性的对体内Cys进行识别是探针设计的关键所在，这也就需要探针分子具有较好的抗干扰性——专一性。然而就目前现有的Cys探针存在着响应时间慢和选择专一性差等问题，本专利通过分子设计，通过电子效应来提高化合物对Cys的响应速度；并且利用专一识别位点提高探针的专一性。
发明内容
针对目前有机小分子荧光探针在Cys分子的检测中所面临的问题，本发明通过分子设计，合成出一种具有响应时间快和选择性高的Cys荧光探针。
本发明采用以下技术方案：
一种识别半胱氨酸的小分子荧光探针，其特征在于，它的分子式为C19H15NO2，具有式（I）所示结构式：。
一种上述识别半胱氨酸的小分子荧光探针的制备方法，其特征在于，它包括如下步骤：
氮气氛围下，将化合物1、化合物2和哌啶加至反应器中，以乙醇作为反应溶剂，于氮气氛围下加热回流5h后，确认反应完全，分离提取即得到目标探针化合物NP-Cys；所述化合物1的结构式如下：
；所述化合物2的结构式如下：。该探针的具体合成路线如下：
所述的分离提取的方法为：先用二氯甲烷萃取，无水硫酸钠干燥，然后旋干溶剂后用柱色谱分离得到产物。
本发明Cys探针的用途：该荧光探针可以应用于水环境和生物细胞体系中Cys的传感检测；所述的传感检测包含荧光检测和细胞成像检测。
本发明的有益效果是：（1）探针的合成只需要一步就可以完成，且后处理过程相对简单；（2）本发明实现了Cys分子探针的选择性快速检测，并且选择性好，抗其他分子干扰能力强。基于其特异性且显著的颜色变化，该试剂可作为显示水溶液中和生物细胞内Cys分子存在的专一性指示剂，可进行实时定性及定量的目视比色法检测。故而，本发明是一种简单，快速，灵敏的Cys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1中探针NP-Cys的1HNMR图谱；
图2是探针NP-Cys随Cys的加入荧光强度的变化情况图；
图3是探针NP-Cys随时间变化荧光强度变化情况图；
图4是探针NP-Cys选择性柱状图数据，其中1：Cys；2：GSH；3：Hcy；4：Al3+；5：Ca2+；6：Co2+；7：Cu+；8：Cu2+；9：Mg2+；10：S2-；11：SO3 2-；12：Ni2+；13：Zn2+；
图5是探针NP-Cys应用于细胞中检测内源性Cys荧光成像图，a）探针浓度为20μM加入到HeLa细胞中培养0.5h后明场图；b）a）的荧光成像图；c）将a）和b）成像图叠加图；d）将1mM的NEM加至育有HeLa细胞的培养液中在二氧化碳培养箱中培养1h，然后加入20μM探针孵育0.5h，明场成像图；e）将d）用蓝光进行激发得到的成像图；f）d）和e）成像图叠加图；g）将600μM的Cys加至育有HeLa细胞的培养液中在二氧化碳培养箱中培养1h，然后加入20μM探针孵育0.5h，明场成像图；h）将g）用蓝光进行激发得到的成像图；i）g）和h）成像图叠加图。
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。
实施例1
探针化合物NP-Cys的合成
将化合物1（0.5mmol，100.0mg）与化合物2（1.1eq.，58.9mg）在氮气氛围下加至反应瓶中，然后将哌啶（1.1eq.46.8mg）和乙醇（5.0mL）一次加至上述反应器中，于氮气氛围下在加热回流5h后，点板检测反应至原料消失，萃取，使用二氯甲烷萃取，无水Na2SO4干燥，减压旋干溶剂得粗产品，并用硅胶柱进行分离得到探针化合物NP-Cys，硅胶颗粒大小为200-300目，产率为85%。1H-NMR(400MHz,CDCl3)δ8.74(d,J=3.6Hz,1H),8.66(s,1H),8.41(d,J=15.2Hz,1H),8.16(dd,J=8.4,2.8Hz,1H),7.92(d,J=9.2Hz,1H),7.82-7.80(m,3H),7.54(d,J=8.0Hz,1H),7.38-7.35(m,1H),7.22(dd,J=8.8,2.4Hz,1H),7.18(d,J=2.4Hz1H),3.96(s,3H).该探针的1HNMR图谱见图1。
实施例2
探针化合物NP-Cys荧光探针随Cys加入当量的增加荧光谱图的变化
取实施例1制备的探针NP-Cys溶于N,N-二甲基甲酰胺（DMF）中，制成1mmol/L储备液。从储备液中取出30μL加入到5mL的离心管当中，加入不同当量（0-30eq.）的Cys标准溶液，用PBS缓冲溶液（0.1mol/L，pH=7.5）与MeOH体积比为19:1的溶液稀释至3mL，以360nm为激发光测量其荧光性质。荧光光谱如图2所示。由图2可见，随着Cys加入当量的增加荧光逐渐增强。
实施例3
探针NP-Cys对随时间变化的荧光谱图的变化
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，加入Cys(20eq.)标准溶液，用MeOH/PBS(19:1,v/v)稀释至3mL(10μM)，以360nm为激发光测量其荧光性质。荧光光谱如图3所示。由图3可见，加入探针NP-Cys后，直接加入Cys，随时间的增加荧光强度迅速达到最大，实现了Cys的快速检测。
实施例4
化合物NP-Cys荧光探针对不同离子的选择性
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Cys标准溶液，20min后以360nm为激发光检测溶液的荧光发射光谱变化，结果见图4。由图4可以发现，其他干扰离子对化合物NP-CYS的荧光几乎没有影响，而Cys溶液的加入使化合物NP-Cys的荧光显著增强。
实施例5
化合物NP-Cys荧光探针对细胞内源性Cys荧光成像
我们将本发明探针应用于HeLa细胞中对内源性的Cys进行荧光成像（图5）。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）用蓝光进行激发观得到成像图；c）将a）和b）图成像叠加；d）将1mM的NEM加至育有HeLa细胞的培养液中在二氧化碳培养箱中培养1h，然后加入20μM探针孵育0.5h，明场成像，可以看到细胞大致的轮廓；e）将d）用蓝光进行激发观得到成像图；f）将d）和e）图成像叠加；g）将600μM的Cys加至育有HeLa细胞的培养液中在二氧化碳培养箱中培养1h，然后加入20μM探针孵育0.5h，明场成像，可以看到细胞大致的轮廓；h）将g）用蓝光进行激发观得到成像图；i）将g）和h）图成像叠加；说明此荧光探针可以对内源性的Cys进行荧光成像。

Claims (4)

1.一种识别半胱氨酸的小分子荧光探针，其特征在于，它的分子式为C19H15NO2，具有式（I）所示结构式：。
2.一种权利要求1所述的识别半胱氨酸的小分子荧光探针的制备方法，其特征在于，它包括如下步骤：
氮气氛围下，将化合物1、化合物2和哌啶加至反应器中，以乙醇作为反应溶剂，于氮气氛围下加热回流5h后，确认反应完全，分离提取即得到目标探针化合物NP-Cys；所述化合物1的结构式如下：
；所述化合物2的结构式如下：。
3.根据权利要求2所述的识别半胱氨酸的小分子荧光探针的制备方法，其特征在于，所述的分离提取的方法为：先用二氯甲烷萃取，无水硫酸钠干燥，然后旋干溶剂后用柱色谱分离得到产物。
4.一种权利要求1或2所述的识别半胱氨酸的小分子荧光探针的应用，其特征在于，该荧光探针可以应用于水环境和生物细胞体系中Cys的传感检测；所述的传感检测包含荧光检测和细胞成像检测。
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109369570A (zh) * 2018-12-03 2019-02-22 山东交通学院 一种快速专一性识别半胱氨酸的小分子荧光探针及其制备方法和应用
CN109897625A (zh) * 2017-12-08 2019-06-18 南京理工大学 选择性检测半胱氨酸荧光探针及其合成方法和应用

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101726476A (zh) * 2009-11-12 2010-06-09 浙江大学 检测生物巯基分子的荧光探针及制备和使用方法
CN104447421A (zh) * 2014-10-28 2015-03-25 苏州罗兰生物科技有限公司 一种新型半胱氨酸和同型半胱氨酸荧光探针的制备与应用
WO2015198341A1 (en) * 2014-06-25 2015-12-30 Council Of Scientific And Industrial Research Method for selective detection and estimation of histidine and cystein
CN105418662A (zh) * 2015-10-14 2016-03-23 济南大学 一种基于bodipy的半胱氨酸荧光探针化合物的制备与应用

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101726476A (zh) * 2009-11-12 2010-06-09 浙江大学 检测生物巯基分子的荧光探针及制备和使用方法
WO2015198341A1 (en) * 2014-06-25 2015-12-30 Council Of Scientific And Industrial Research Method for selective detection and estimation of histidine and cystein
CN104447421A (zh) * 2014-10-28 2015-03-25 苏州罗兰生物科技有限公司 一种新型半胱氨酸和同型半胱氨酸荧光探针的制备与应用
CN105418662A (zh) * 2015-10-14 2016-03-23 济南大学 一种基于bodipy的半胱氨酸荧光探针化合物的制备与应用

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
WEIYING LIN，等: "A Sensitive and Selective Fluorescent Thiol Probe in Water Based on the Conjugate 1,4-Addition of Thiols to a,b-Unsaturated Ketones", 《CHEM. EUR. J.》 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109897625A (zh) * 2017-12-08 2019-06-18 南京理工大学 选择性检测半胱氨酸荧光探针及其合成方法和应用
CN109897625B (zh) * 2017-12-08 2022-04-19 南京理工大学 选择性检测半胱氨酸荧光探针及其合成方法和应用
CN109369570A (zh) * 2018-12-03 2019-02-22 山东交通学院 一种快速专一性识别半胱氨酸的小分子荧光探针及其制备方法和应用
CN109369570B (zh) * 2018-12-03 2022-04-26 山东交通学院 一种快速专一性识别半胱氨酸的小分子荧光探针及其制备方法和应用

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